EP4279568A1 - Utilisation de terpènes ou terpénoïdes non canoniques comme substances chimiques aromatiques - Google Patents

Utilisation de terpènes ou terpénoïdes non canoniques comme substances chimiques aromatiques Download PDF

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EP4279568A1
EP4279568A1 EP22174377.6A EP22174377A EP4279568A1 EP 4279568 A1 EP4279568 A1 EP 4279568A1 EP 22174377 A EP22174377 A EP 22174377A EP 4279568 A1 EP4279568 A1 EP 4279568A1
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Prior art keywords
composition
canonical
combination
conferring
methyl
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German (de)
English (en)
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Svenja Sommer
Marco Alexander Fraatz
Holger Zorn
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0007—Aliphatic compounds
    • C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C11B9/0046—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings
    • C11B9/0049—Essential oils; Perfumes compounds containing condensed hydrocarbon rings containing only two condensed rings the condensed rings sharing two common C atoms

Definitions

  • the present invention relates to the use of non-canonical terpenes or terpenoids, mixtures thereof, stereoisomers thereof or mixtures of different stereoisomers thereof as an aroma chemical; to the use thereof for modifying and/or enhancing the aroma of a composition; to a composition comprising such non-canonical terpenes or terpenoids, mixtures thereof, stereoisomers thereof or mixtures of different stereoisomers thereof and at least one of aroma chemicals different from said non-canonical terpenes and terpenoids, non-aroma chemical carriers, anti-oxidants and deodorant-active agents; to a method for preparing an aroma chemical composition comprising incorporating said non-canonical terpenes or terpenoids, mixtures thereof, stereoisomers thereof or mixtures of different stereoisomers thereof into the composition or comprising mixing said non-canonical terpenes or terpenoids, mixtures thereof, stereoisomers thereof or mixtures of different stereoisomers thereof simultaneously or consecutively
  • Aroma chemicals, especially fragrances, are of great interest especially in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural origin are mostly expensive, often limited in their available amount and, on account of fluctuations in environmental conditions, are also subject to variations in their content, purity etc. To circumvent these undesirable factors, it is therefore of great interest to create synthetic substances which have sensory properties that resemble more expensive natural fragrances or which have novel and interesting sensory profiles.
  • aroma chemicals should have advantageous odiferous (olfactory) or gustatory properties.
  • aroma chemicals should also have additional positive secondary properties, such as e.g. an efficient preparation method, the possibility of providing better sensory profiles as a result of synergistic effects with other aroma chemicals, a higher stability in a wide range of compositions as well as under certain application conditions, a higher extendability and/or a better staying power.
  • Terpenes and terpenoids form a large and heterogeneous group of chemical compounds, whose common feature is that their backbone is based on isoprene units:
  • the carbon number in the backbone of terpenes and terpenoids is thus a multiple of 5 (i.e. n ⁇ 5 carbon atoms; n being an integer; isoprene rule).
  • Terpenes and terpenoids occur naturally in organisms, often in form of secondary metabolites in plants, animals and microorganisms. Terpenes are pure hydrocarbons of the molecular formula (C 5 H 8 ) n , whereas terpenoids contain additional functional groups, usually oxygen-containing groups. Terpenes and terpenoids wherein n is 1 are termed hemiterpenes and hemiterpenoids, respectively, terpenes and terpenoids wherein n is 2 are termed monoterpenes and monoterpenoids, respectively, and terpenes and terpenoids wherein n is 3 are termed sesquiterpenes and sesquiterpenoids, respectively.
  • Short-chain terpenes and terpenoids are relevant as aroma compounds, including hemi- (C 5 ), mono- (C 10 ), and sesquiterpenes and -terpenoids (C 15 ).
  • C 5 hemi-
  • C 10 mono-
  • sesquiterpenes and -terpenoids C 15
  • a known examples for a hemiterpenoid with aroma properties is prenol, which occurs e.g.
  • examples for monoterpenoids and monoterpenes with aroma properties include linalool with a citrus- and lavender-like scent, thymol with a thyme-like flavor, and limonene with a fresh, orange-like odor of the (R)-enantiomer and a pine-like flavor of the (S)-enantiomer; and farnesol and (S)-nerolidol are examples of sesquiterpenoids with aroma properties; they are associated with a flowery scent.
  • terpenes and terpenoids can however also differ from the sequential condensation of C 5 units, resulting thus in structures with a number of carbon atoms different from a multiple of five. These terpenes/terpenoids are called non-canonical.
  • Non-canonical terpenes or terpenoids are also available via biosynthesis involving the action of methyltransferases, enzymes which catalyze the addition of methyl groups to the prenyl pyrophosphate precursors, thereby changing the final number of carbon atoms of the terpene or terpenoid structures.
  • the methyltransferases sometimes also cyclize the classical isoprenyl diphosphate substrates.
  • the invention relates to the use of a non-canonical terpene or of a non-canonical terpenoid or of a stereoisomer thereof or of a mixture of different stereoisomers thereof or of a mixture of different non-canonical terpenes and/or non-canonical terpenoids as an aroma chemical.
  • the invention relates furthermore to the use of a non-canonical terpene or terpenoid or of a stereoisomer thereof or of a mixture of different stereoisomers thereof or of a mixture of different non-canonical terpenes and/or terpenoids for modifying and/or enhancing the aroma of a composition.
  • the invention relates moreover to a composition
  • a composition comprising a non-canonical terpene or a non-canonical terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or non-canonical terpenoids, and at least one further component selected from the group consisting of aroma chemicals different from said non-canonical terpenes and non-canonical terpenoids, non-aroma chemical carriers, anti-oxidants and deodorant-active agents.
  • the invention relates also to a method for preparing an aroma chemical composition, in particular a fragranced composition, specifically a fragranced ready-to-use composition, comprising incorporating a non-canonical terpene or a non-canonical terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or non-canonical terpenoids into said composition; or mixing a non-canonical terpene or a non-canonical terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or non-canonical terpenoids simultaneously or consecutively with the other components of said composition or with pre-formed mixtures of a part of the other components of said composition.
  • the invention relates also to a method for conferring an aroma, preferably a fragrance, to a composition, comprising incorporating a non-canonical terpene or a non-canonical terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or non-canonical terpenoids into said composition.
  • aroma refers to a sensory property and comprises an odor and/or a flavor.
  • aroma chemical denotes a substance which is used to obtain an aroma impression (the term “aroma impression” is used interchangeably herein with the term “note”) and comprises its use to obtain an olfactory and/or a flavor impression.
  • olfactory impression or “odor impression” denotes an odor impression without any positive or negative judgement
  • cent impression or “fragrance impression” (used interchangeably herein) as used herein is connected to an odor impression which is generally felt as pleasant.
  • a "fragrance” or “scent” denotes an aroma chemical which predominately induces a pleasant odor impression.
  • a flavor denotes an aroma chemical which induces a taste impression.
  • aroma profile denotes the overall aroma impression of an aroma chemical and is composed of the individual aroma impressions of an aroma chemical.
  • aroma composition refers to a composition which induces an aroma.
  • aroma composition comprises "odor composition” and/or "flavor composition”.
  • An odor composition is a composition which predominately induces an odor impression, whereas a flavor composition is a composition which predominantly induces a taste impression.
  • odor composition comprises "fragrance composition” or “scent composition” (used interchangeably herein), which predominately induce an odor impression which is generally felt as pleasant.
  • “Pleasant odor”, “pleasant odor impression”, “pleasant odiferous properties”, "odor impression felt as pleasant” and similar terms are hedonistic expressions which describe the niceness and conciseness of an odor impression conveyed by an aroma chemical.
  • the more general hedonistic expressions "advantageous sensory properties” or “advantageous organoleptic properties” describe the niceness and conciseness of an organoleptic impression conveyed by an aroma chemical.
  • the terms “organoleptic” and “sensory” relate to olfactory or flavor properties.
  • “Niceness” and “conciseness” are terms which are familiar to the person skilled in the art, a perfumer.
  • Niceness generally refers to a spontaneously brought about, positively perceived, pleasant sensory impression. However, “nice” does not have to be synonymous with “sweet”. “Nice” can also be the odor of musk or sandalwood. “Conciseness” generally refers to a spontaneously brought about sensory impression which - for the same test panel - brings about a reproducibly identical reminder of something specific. For example, a substance can have an odor which is spontaneously pronounced of that of an "apple”: the odor would then be concisely of "apples”. If this apple odor were very pleasant because the odor is reminiscent, for example, of a sweet, fully ripe apple, the odor would be termed "nice". However, the odor of a typical apple tart can also be concise. If both reactions arise upon smelling the substance, in the example thus a nice and concise apple odor, then this substance has particularly advantageous sensory properties.
  • odor-intensive substances refers to substances or aroma chemicals exhibiting intense odor impressions. Intense odor impressions are to be understood as meaning those properties of aroma chemicals which permit a striking perception even in very low gas space concentrations.
  • the intensity can be determined via a threshold value determination.
  • a threshold value is the concentration of a substance in the relevant gas space at which an odor impression can just still be perceived by a representative test panel, although it no longer has to be defined.
  • tenacity describes the evaporation behavior over time of an aroma chemical.
  • the tenacity can for example be determined by applying the aroma chemical to a test strip, and by subsequent olfactory evaluation of the odor impression of the test strip.
  • aroma chemicals with high tenacity the time span after which the panel can still identify an aroma impression is long.
  • substantially describes the interaction of an aroma chemical with a surface, such as for example the skin or a textile, especially after subsequent treatment of the surface, such as for example washing.
  • the substantivity can for example be determined by washing a textile with a textile detergent composition comprising the aroma chemical and subsequent olfactory evaluation of the textile directly after washing (wet textile) as well as evaluation of the dry textile after prolonged storage.
  • Stability describes the behavior of an aroma chemical upon contact with oxygen, light and/or other substances.
  • An aroma chemical with high stability maintains its aroma profile over a long period in time, preferably in a large variety of compositions and under various storage conditions.
  • the tenacity, the substantivity as well as the stability of the aroma chemical in the compositions should preferably be high.
  • boost boosting
  • boost boost
  • boosting boost
  • boost boost
  • boosting boost
  • boost boost
  • Booster effects are particularly desired in fragrance composition when top-note-characterized applications are required, in which the odor is to be conveyed particularly quickly and intensively, for example in deodorants, air fresheners or in the taste sector in chewing gums.
  • terpenes and terpenoids are a group of chemical compounds whose common feature is that their backbone is based on isoprene units.
  • the carbon number in their backbone is thus a multiple of 5 (i.e. n ⁇ 5 carbon atoms; n being an integer; isoprene rule).
  • Terpenes are pure hydrocarbons of the molecular formula (C 5 H 8 ) n
  • Terpenes and terpenoids wherein n is 1 are termed hemiterpenes and hemiterpenoids, respectively; terpenes and terpenoids wherein n is 2 are termed monoterpenes and monoterpenoids, respectively; and terpenes and terpenoids wherein n is 3 are termed sesquiterpenes and sesquiterpenoids, respectively.
  • Non-canonical terpenes and non-canonical terpenoids are structurally related to terpenes or terpenoids; due to a different biosynthesis or structural modification, the number of their carbon atoms is however different from a multiple of five.
  • Metalated in context with the present non-canonical terpenes or terpenoids means that one or more hydrogen atoms bound to a carbon atom of a basic, “classical” terpene or terpenoid structure (i.e. having n ⁇ 5 carbon atoms) is/are replaced by a methyl (CH 3 ) group.
  • non-canonical terpene or terpenoid is defined to be a specific, defined compound (and not to be a mixture of different non-canonical terpenes and/or terpenoids)
  • Matture of different non-canonical terpenes and/or terpenoids means a mixture of two or more different non-canonical terpenes or a mixture of two or more different non-canonical terpenoids or a mixture of one or more non-canonical terpenes and one or more non-canonical terpenoids.
  • stereoisomers as used in context with the present invention relates to optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one stereogenic center in the molecule, as well as to (Z/E) isomers (due to the presence of correspondingly substituted double bonds or ring systems).
  • the non-canonical terpene or terpenoid is a methylated or methylenated terpene or terpenoid.
  • a methylated terpene or terpenoid one or more hydrogen atoms bound to a carbon atom of the basic, "classical" terpene or terpenoid structure (i.e. having n ⁇ 5 carbon atoms) is/are replaced by a methyl (CH 3 ) group.
  • the non-canonical terpene is derived from a hemiterpene (C 5 ), monoterpene (C 10 ) or sesquiterpene (C 15 ), and the non-canonical terpenoid is derived from a hemiterpenoid (C 5 ), monoterpenoid (C 10 ) or sesquiterpenoid (C 15 ).
  • the non-canonical hemiterpene or hemiterpenoid contains thus 5+x carbon atoms, x being an integer and generally 1, 2 or 3, most frequently 1 or 2; the non-canonical monoterpene or monoterpenoid contains 10+x carbon atoms, x being an integer and generally 1, 2 or 3, most frequently 1 or 2; and the non-canonical sesquiterpene or sesquiterpenoid contains 15+x carbon atoms, x being an integer and generally 1, 2 or 3, most frequently 1 or 2.
  • the non-canonical terpenoid contains a hydroxyl group as only functional group.
  • the non-canonical terpene or terpenoid is derived from bornane, camphene, 3-carene, limonene, prenol, isoprenol, ⁇ -fenchol, ⁇ -terpineol, citronellol, geraniol, nerol, linalool or farnesol and is even more preferably selected from the group consisting of methylated or methylenated bornane, camphene, 3-carene, limonene, prenol, isoprenol, ⁇ -fenchol, ⁇ -terpineol, citronellol, geraniol, nerol, linalool and farnesol.
  • the basic terpene or terpenoid is preferably methylated or methylenated with 1, 2 or 3, more preferably with 1 or 2 methyl and/or methylene groups.
  • the non-canonical terpene or terpenoid is selected from the group consisting of monomethylenated or monomethylated bornane, monomethylated camphene, monomethylated 3-carene, monomethylated limonene, mono- or dimethylated prenol, mono- or dimethylated isoprenol, monomethylated ⁇ -fenchol, monomethylated ⁇ -terpineol, monomethylated citronellol, monomethylated geraniol, monomethylated nerol, monomethylated linalool and monomethylated farnesol.
  • the non-canonical terpene or terpenoid is selected from the group consisting of 2-methylenebornane, 1-methylcamphene, 4-methyl-3-carene, 2-methyllimonene, 2-methylisoprenol, 4-methylisoprenol, 5-methylisoprenol, 2,4-dimethylisoprenol, 2,5-dimethylisoprenol, 4,4-dimethylisoprenol, 4,5-dimethylisoprenol, 5,5-dimethylisoprenol, 2-methylprenol, 4-methylprenol, 2,4-dimethylprenol, 4,4-dimethylprenol, 4,5-dimethylprenol, 2-methyl- ⁇ -fenchol, 2-methyl- ⁇ -terpineol, 2-methylcitronellol, 2-methylgeraniol, 4-methylgeraniol, 8-methylgeraniol, 2-methylnerol, 4-methylnerol
  • the non-canonical terpene or terpenoid is selected from the group consisting of 2-methylenebornane, 1-methylcamphene, (S)-1-methylcamphene, 4-methyl-3-carene, 2-methyllimonene, 2-methylisoprenol, 4-methylisoprenol, (E)-4-methylisoprenol, (Z)-4-methylisoprenol, 5-methylisoprenol, 2,4-dimethylisoprenol, 2,5-dimethylisoprenol, 4,4-dimethylisoprenol, 4,5-dimethylisoprenol, 5,5-dimethylisoprenol, 2-methylprenol, 4-methylprenol, (Z)-4-methylprenol, (E)-4-methylprenol, 2,4-dimethylprenol, 4,4-dimethylprenol, 4,5-dimethylprenol, 2-methyl-methyl
  • the non-canonical terpene or terpenoid is selected from the group consisting of 2-methylenebornane, (S)-1-methylcamphene, 4-methyl-3-carene, 2-methyllimonene, 2-methylisoprenol, (E)-4-methylisoprenol, (Z)-4-methylisoprenol, 5-methylisoprenol, 2,4-dimethylisoprenol, 2,5-dimethylisoprenol, 4,4-dimethylisoprenol, 4,5-dimethylisoprenol, 5,5-dimethylisoprenol, 2-methylprenol, (Z)-4-methylprenol, (E)-4-methylprenol, 2,4-dimethylprenol, 4,4-dimethylprenol, 4,5-dimethylprenol, (S)-2-methyl- ⁇ -fenchol, 2-methyl- ⁇ -terpineol, 2-methyl-
  • the specified compounds have following structures: 2-methylenebornane (1), 1-methylcamphene (2), 4-methyl-3-carene (3), 2-methyllimonene (4), 2-methylisoprenol (5), 4-methylisoprenol (6), (Z)-4-methylisoprenol (Z-6), (E)-4-methylisoprenol (E-6), 5-methylisoprenol (7), 2,4-dimethylisoprenol (8), 2,5-dimethylisoprenol (9), 4,4-dimethylisoprenol (10), 4,5-dimethylisoprenol (11), 5,5-dimethylisoprenol (12), 2-methylprenol (13), 4-methylprenol (14), (E)-4-methylprenol (E-14), (Z)-4-methylprenol (Z-14), 2,4-dimethylprenol (15), 4,4-dimethylprenol (16), 4,5-dimethylpre
  • the asterisk denotes the methyl or methylene group(s) which distinguish(es) the non-canonical terpene/terpenoid from the corresponding basic, "classical” terpene/terpenoid. Wavy bonds indicate that the stereochemistry is not determined or the compound is a mixture of the possible stereoisomers.
  • non-canonical terpenes and terpenoids different from those listed above can be prepared by or in analogy to methods known in the art, generally by biotechnological methods as described, for example, by C. Ignea et al., Nat. Chem. Biol. 2018, 14, 1090-1098 , M.J. Kschowak et al., PLoS One 2018, 13, e0196082 or L. Drummond et al., ACS Synth. Biol. 2019, 8, 1303-1313 .
  • an easy-to-cultivate microorganism suitable for biotechnological processes mostly a bacterium, such as Escherichia coli, or a yeast, such as Saccharomyces cerevisae, is modified by transferring genes encoding prenyl methyltransferases (just by way of example geranyl pyrophosphate transferase from Streptomyces coelicolor or isopentenyl pyrophosphate methyltransferase from Streptomyces monomycini ) and optionally also the suitable synthase (just by way of example 2-methylene bornane synthase from Pseudomonas fluorescens for producing 2-methylenebornane).
  • the thusly modified microorganism is used for the production of the desired compound. If the microorganism produces more than one compound, this can be isolated from the obtained mixture by usual means, such as chromatography, or by distillative or extractive methods.
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers and the mixtures of different non-canonical terpenes and/or terpenoids are used as a fragrance.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers and the mixture of different non-canonical terpenes and/or terpenoids is generally used in a ready-to-use composition, in particular in a fragranced ready-to-use composition.
  • "Fragranced ready-to-use composition” refers to a ready-to-use composition which predominately induces a pleasant odor impression.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers and the mixture of different non-canonical terpenes and/or terpenoids is also used for modifying and/or enhancing the aroma of a composition; in particular for modifying and/or enhancing the fragrance impression of a composition; specifically for modifying the scent character of a fragranced ready-to-use composition.
  • Fragranced ready-to-use compositions are for example compositions used in personal care, in home care, in industrial applications as well as compositions used in other applications, such as pharmaceutical compositions or crop protection compositions.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers and the mixture of different non-canonical terpenes and/or terpenoids is used in a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • a composition selected from the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers and the mixture of different non-canonical terpenes and/or terpenoids exhibit advantageous secondary properties.
  • they can provide better sensory profiles as a result of synergistic effects with other fragrances, which means that they can provide a booster effect for other fragrances. They are therefore suitable as boosters for other fragrances.
  • another aspect of the invention relates to the use of non-canonical terpenes or terpenoids, of stereoisomers thereof, of mixtures of different stereoisomers and of mixtures of different non-canonical terpenes and/or terpenoids for modifying the scent character of a fragranced composition; and specifically to the use as a booster for other fragrances.
  • Booster effect means that the substances enhance and intensify in perfumery formulations the overall impression of the mixture.
  • Menthyl methyl ether intensifies the perfumery or taste mixtures of peppermint oils and particularly in top notes brings about a considerably more intensive and more complex perception although the ether itself, being a pure substance, develops no particular intensive odor at all.
  • Hedione ® methyl dihydrojasmonate
  • Booster effects are particularly desired when top-note-characterized applications are required, in which the odor impression is to be conveyed particularly quickly and intensively, for example in deodorants, air fresheners or in the taste sector in chewing gums.
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers and the mixtures of different non-canonical terpenes and/or terpenoids are generally used in an overall amount of 0.1 to 20% by weight, preferably in an amount of 0.5 to 5% by weight, in particular in an amount of from 0.6 to 3% by weight, based on the total weight of the fragrance mixture.
  • non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers and the mixture of different non-canonical terpenes and/or terpenoids can have further positive effects on the composition in which they are used. For example, they can enhance the overall performance of the composition into which they are incorporated, such as the stability, e.g. the formulation stability, the extendability or the staying power of the composition.
  • a further embodiment of the invention is directed to a method of preparing an aroma chemical composition, in particular a fragranced composition, especially a fragranced ready-to-use composition, comprising incorporating at a non-canonical terpene or terpenoid, a stereoisomer thereof, a mixture of different stereoisomers or a mixture of different non-canonical terpenes and/or terpenoids into the target composition, e.g. a ready-to-use composition, resulting in an aroma chemical composition, in particular in a fragranced composition, especially in a fragranced ready-to-use composition.
  • the invention is directed to a method of preparing an aroma chemical composition, in particular a fragranced composition, especially a fragranced ready-to-use composition, comprising mixing the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers or the mixture of different non-canonical terpenes and/or terpenoids with at least one aroma chemical different therefrom and/or with at least one non-aroma chemical carrier and/or with at least one antioxidant and/or with at least one deodorant-active agent.
  • Suitable and preferred aroma chemicals different from said non-canonical terpenes and terpenoids, non-aroma chemical carriers, antioxidants and deodorant-active agents are described below.
  • the method can be carried out by mixing the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers or the mixture of different non-canonical terpenes and/or terpenoids, as defined above, and at least one further component selected from the group consisting of aroma chemicals different therefrom, non-aroma chemical carriers, antioxidants and deodorant-active agents.
  • the invention is also directed to a method for modifying the scent character of an aroma chemical composition, in particular of a fragranced composition, especially of a fragranced ready-to-use composition, comprising incorporating the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers or the mixture of different non-canonical terpenes and/or terpenoids into an aroma chemical composition, in particular into a fragranced composition, especially into a fragranced ready-to-use composition.
  • the invention is directed to a method of preparing a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, comprising including the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers or the mixture of different non-canonical terpenes and/or terpenoids as defined above in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: earthy, coniferous forest, resinous or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methylenebornane in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, coniferous forest, woody, fruity or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (S)-1-methylcamphene in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: fruity, coniferous forest, resinous, sweetish, pepper, mint, citrus or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4-methyl-3-carene in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, terpene, mushroom or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methyllimonene in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, sweetish, coniferous forest, fruity or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: green, grass, herbal, coniferous forest, apple or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (E)-4-methylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: flowery, green, fruity, apple or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (Z)-4-methylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: pungent, solvent, glue, varnish or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 5-methylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: coniferous forest, green, resinous or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2,4-dimethylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, coniferous forest, mint, green, varnish or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2,5-dimethylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: green, citrus, flowery, soapy, grass or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4,4-dimethylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, woody, coniferous forest or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4,5-dimethylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: coniferous forest, resinous, woody or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 5,5-dimethylisoprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: plastic, terpene-like or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: plastic, terpene-like, chemical or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (Z)-4-methylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: sweetish, flowery, green, citrus, fresh, resinous or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (E)-4-methylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: resinous, woody, coniferous forest, glue, sweetish or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2,4-dimethylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: sweetish, fruity or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4,4-dimethylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: woody, resinous, plastic or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4,5-dimethylprenol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: earthy, mouldy, moss, beetroot or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including (S)-2-methyl- ⁇ -fenchol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: sweetish, green or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methyl- ⁇ -terpineol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: flowery, citrus, rose, sweetish, ethereal, fruity or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methylcitronellol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: flowery, citrus, resinous, rose, sweetish or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including a mixture of 2-methylgeraniol and 2-methylnerol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: citrus, lemon, lemon peel or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including a mixture of 4-methylgeraniol and 4-methylnerol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: flowery, resinous, sweetish, citrus, varnish or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including a mixture of 8-methylgeraniol and 8-methylnerol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: flowery, citrus, sweetish, fruity, bergamot, blueberry, lavender or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 2-methyllinalool in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the invention is directed to a method for imparting one of the olfactory notes: citrus, resinous, green or any combination thereof to a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition, which comprises including 4-methylfarnesol in a perfume composition, body care composition, product for oral and dental hygiene, hygiene article, cleaning composition, textile detergent composition, composition for scent dispensers, food, food supplement, pharmaceutical composition or crop protection composition.
  • the above particular methods can also be carried out by mixing the specified non-canonical terpene/terpenoid and the other components of the specified composition simultaneously or consecutively with each other.
  • the invention relates moreover to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one further component selected from the group consisting of aroma chemicals different from said non-canonical terpenes and terpenoids, non-aroma chemical carriers, anti-oxidants and deodorant-active agents.
  • non-aroma chemical carriers, anti-oxidants and deodorant-active agents are of course also different from said non-canonical terpenes or terpenoids.
  • the non-aroma chemical carrier is in particular selected from the group consisting of surfactants, oil components (emollients) and solvents.
  • the composition comprises a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one further component selected from the group consisting of aroma chemicals different from said non-canonical terpenes and terpenoids, surfactants, oil components, solvents, anti-oxidants and deodorant-active agents.
  • the pleasant aroma, low volatility and excellent solubility make the non-canonical terpenes or terpenoids suitable components in compositions where a pleasing aroma is desirable.
  • said composition is preferably an aroma chemical composition, more preferably an odor composition and in particular a fragrance composition.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids as defined above and at least one further component selected from the group consisting of oil components, solvents, anti-oxidants and deodorant-active agents.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one aroma chemical.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one non-aroma chemical carrier.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one surfactant.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one oil component.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one solvent.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one anti-oxidant.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one deodorant-active agent.
  • the non-canonical terpenes or terpenoids or the stereoisomers thereof or the mixture of different stereoisomers thereof or the mixture of different non-canonical terpenes and/or terpenoids can preferably be used in aroma compositions.
  • the aroma composition is an odor composition, i.e. a composition inducing an odor impression, and is in particular a fragrance composition, i.e. a composition inducing a pleasant odor.
  • composition according to the invention can be selected from, but is not limited to, the group consisting of perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • body care compositions including cosmetic compositions
  • cleaning compositions including dishwashing compositions
  • textile detergent compositions including textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • Aroma chemicals (different from said non-canonical terpenes and terpenoids)
  • non-canonical terpenes or terpenoids By virtue of the physical properties of the above-defined non-canonical terpenes and terpenoids, combinations of said compounds have particularly good, virtually universal solvent properties for and in aroma chemicals and other customary ingredients in aroma compositions such as, in particular, fragrance compositions. Therefore, the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof and the mixtures of different non-canonical terpenes and/or terpenoids are well combinable with aroma chemicals which are different from the above-defined non-canonical terpenes and terpenoids, allowing, in particular, the creation of aroma compositions (preferably fragrance compositions) having novel advantageous sensory profiles. Especially, as already explained above, the combinations can boost the sensory profile of aroma chemicals (such as for example of fragrances) wherein said aroma chemicals are different from the above-defined non-canonical terpenes and terpenoids.
  • aroma chemicals preferably fragrance
  • compositions of the invention can comprise at least one aroma chemical that is different from compounds the above-defined non-canonical terpenes and terpenoids.
  • Said at least one aroma chemical can for example be 1, 2, 3, 4, 5, 6, 7, 8 or more aroma chemicals, selected from the group consisting of: Geranyl acetate (3,7-dimethyl-2,6 octadien-1 yl acetate), alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate (Phenirat 1 ), dihydromyrcenol (2,6-dimethyl-7-octen-2-ol), methyl dihydrojasmonate (preferably with a content of cis isomer of more than 60 wt.%) (Hedione 9 , Hedione HC 9 ), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydro-cyclopenta[g]benzopyran (Gala
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and at least one aroma chemical selected from the group consisting of methyl benzoate, benzyl acetate, geranyl acetate, 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol and linalool.
  • a further embodiment of the invention relates to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids and 2-isobutyl-4-methyltetrahydro-2H-pyran-4-ol.
  • a further embodiment of the invention relates to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and methyl benzoate.
  • a preferred embodiment of the invention relates to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one further aroma chemical selected from the group consisting of ethylvan-illin, vanillin, 2,5-dimethyl-4-hydroxy-2H-furan-3-one (furaneol) or 3-hydroxy-2-methyl-4H-pyran-4-one (maltol).
  • the aroma chemicals different from said non-canonical terpenes and terpenoids are selected from the group consisting of geranyl acetate, alpha-hexylcinnamaldehyde, 2-phenoxyethyl isobutyrate, dihydromyrcenol, methyl dihydrojasmonate (preferably with a content of cis isomer of more than 60 wt.%), 4,6,6,7,8,8-hexamethyl-1,3,4,6,7,8-hexahydrocyclopenta[g]benzopyran, tetrahydrolinalool, ethyllinalool, benzyl salicylate, 2-methyl-3-(4-tert-butylphenyl)propanal, cinnamyl alcohol, 4,7-methano-3a,4,5,6,7,7a-hexahydro-5-indenyl acetate, 4,7-methano-3a,4,5,6,7,7a
  • a further embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one non-aroma chemical carrier.
  • the at least one non-aroma chemical carrier can be a compound, a mixture of compounds or other additives which has/have no or no noteworthy sensory properties.
  • the non-aroma chemical carrier can serve for the dilution and/or the fixing of the non-canonical terpene or terpenoid and the optionally present at least one aroma chemical, as defined above, or any other component, if comprised in the composition.
  • a further embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one non-aroma chemical carrier selected from the group consisting of solvents, surfactants and oil components.
  • said non-aroma chemical carrier(s) is/are selected from the solvents, surfactants and oil components listed below.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, as described herein and at least one solvent.
  • a “solvent” serves for the dilution of the compound(s) (I) to be used according to the invention and/or any further component of the composition without having its own aroma.
  • the one or more solvent(s) can be present in the composition in amount of 0.01 to 99 wt.% based on the composition.
  • the composition comprises 0.1 to 90 wt.%, preferably 0.5 to 80 wt.% of solvent(s) based on the total weight of the composition.
  • the amount of solvent(s) can be chosen depending on the composition.
  • the composition comprises 0.05 to 10 wt.%, preferably 0.1 to 5 wt.%, more preferably 0.2 to 3 wt.% based on the total weight of the composition.
  • the composition comprises 20 to 70 wt.%, preferably 25 to 50 wt.% of solvent(s) based on the total weight of the composition.
  • Preferred solvents are ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), and benzyl benzoate (BB).
  • DPG dipropylene glycol
  • PDP diethyl phthalate
  • IPM isopropyl myristate
  • TEC triethyl citrate
  • BB benzyl benzoate
  • Especially preferred solvents are selected from the group consisting of ethanol, propylene glycol, dipropylene glycol, triethyl citrate, benzyl benzoate and isopropyl myristate.
  • the solvent is selected from the group consisting of ethanol, isopropanol, dipropylene glycol (DPG), propylene glycol, 1,2-butylene glycol, glycerol, diethylene glycol monoethyl ether, diethyl phthalate (DEP), isopropyl myristate (IPM), triethyl citrate (TEC), benzyl benzoate and mixtures thereof.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers thereof or the mixture of different non-canonical terpenes and/or terpenoids is used according to the present invention in surfactant-containing compositions.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers thereof or the mixture of different non-canonical terpenes and/or terpenoids can especially be used to provide an odor, preferably a fragrance impression to surfactant-containing compositions such as, for example, cleaners (in particular laundry care products and all-purpose cleaners). It can preferably be used to impart a long-lasting clean note to a surfactant comprising composition.
  • One embodiment of the invention is therefore directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one surfactant.
  • the surfactant(s) may be selected from anionic, non-ionic, cationic and/or amphoteric or zwitterionic surfactants.
  • Surfactant-containing compositions such as for example shower gels, foam baths, shampoos, etc., preferably contain at least one anionic surfactant.
  • compositions according to the invention usually contain the surfactant(s), in the aggregate, in an amount of 0 to 40 wt.%, preferably 0 to 20 wt.%, more preferably 0.1 to 15 wt.%, and particularly 0.1 to 10 wt.%, based on the total weight of the composition.
  • nonionic surfactants are fatty alcohol polyglycol ethers, alkylphenol polyglycol ethers, fatty acid polyglycol esters, fatty acid amide polyglycol ethers, fatty amine polyglycol ethers, alkoxylated triglycerides, mixed ethers and mixed formals, optionally partly oxidized alk(en)yl oligoglycosides or glucuronic acid derivatives, fatty acid-N-alkyl glucamides, protein hydrolyzates (particularly wheat-based vegetable products), polyol fatty acid esters, sugar esters, sorbitan esters, polysorbates and amine oxides. If the nonionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution, although they preferably have a narrow-range homolog distribution.
  • Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one -COO (-) or -SO 3 (-) group in the molecule.
  • Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example, cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example, cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines, containing 8 to 18 carbon atoms in the alkyl or acyl group, and cocoacylaminoethyl hydroxyethyl carboxymethyl glycinate.
  • Ampholytic surfactants are also suitable, particularly as co-surfactants.
  • Ampholytic surfactants are surface-active compounds which, in addition to a C 8 to C 18 alkyl or acyl group, contain at least one free amino group and at least one -COOH- or -SO 3 H- group in the molecule and which are capable of forming inner salts.
  • ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N-hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2-alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group.
  • Particularly preferred ampholytic surfactants are N-cocoalk-ylaminopropionate, cocoacylaminoethyl aminopropionate and acyl sarcosine.
  • Anionic surfactants are characterized by a water-solubilizing anionic group such as, for example, a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic group. Dermatologically safe anionic surfactants are known to the practitioner in large numbers from relevant textbooks and are commercially available.
  • alkyl sulfates in the form of their alkali metal, ammonium or alkanolammonium salts
  • alkylether sulfates in the form of their alkali metal, ammonium or alkanolammonium salts
  • alkylether carboxylates acyl isethionates
  • acyl sarcosinates acyl taurines containing linear C 12 -C 18 alkyl or acyl groups
  • sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts.
  • Particularly suitable cationic surfactants are quaternary ammonium compounds, preferably ammonium halides, more especially chlorides and bromides, such as alkyl trimethyl ammonium chlorides, dialkyl dimethyl ammonium chlorides and trialkyl methyl ammonium chlorides, for example, cetyl trimethyl ammonium chloride, stearyl trim ethyl ammonium chloride, distearyl dimethyl ammonium chloride, lauryl dimethyl ammonium chloride, lauryl dimethyl benzyl ammonium chloride and tricetyl methyl ammonium chloride.
  • the readily biodegradable quaternary ester compounds such as, for example, the dialkyl ammonium methosulfates and methyl hydroxyalkyl dialkoyloxyalkyl ammonium methosulfates marketed under the name of Stepantexe and the corresponding products of the Dehyquart ® series, may be used as cationic surfactants.
  • "Es-terquats” are generally understood to be quaternized fatty acid triethanolamine ester salts. They can provide the compositions with particular softness. They are known substances which are prepared by the relevant methods of organic chemistry.
  • Other cationic surfactants suitable for use in accordance with the invention are the quaternized protein hydrolyzates.
  • One embodiment of the invention is directed to a composition a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one oil component.
  • the oil components are typically present in an amount of 0.1 to 80 wt.%, preferably 0.5 to 70 wt.%, more preferably 1 to 60 wt.%, even more preferably 1 to 50 wt.%, in particular 1 to 40 wt.%, more particularly 5 to 25 wt.% and specifically 5 to 15 wt.% based on the total weight of the composition.
  • the oil components may be selected, for example, from Guerbet alcohols based on fatty alcohols containing 6 to 18, preferably 8 to 10, carbon atoms and other additional esters, such as myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl oleate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, cetyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl myristate, stearyl palmitate, stearyl stearate, stearyl isostearate, stearyl oleate, stearyl behenate, stearyl erucate, isostearyl myristate, isostearyl palmitate, isostearyl stearate,
  • esters of C 18 -C 38 alkyl-hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols are also suitable.
  • esters of C 18 -C 38 alkyl-hydroxycarboxylic acids with linear or branched C 6 -C 22 fatty alcohols are especially dioctyl malate, esters of linear and/or branched fatty acids with polyhydric alcohols (for example propylene glycol, dimer dial or trimer triol), triglycerides based on C 6 -C 10 fatty acids, liquid mono-, di- and triglyceride mixtures based on C 6 -C 18 fatty acids, esters of C 6 -C 22 fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids, more particularly benzoic acid, esters of dicarboxylic acids with polyols containing 2 to 10 car- bon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one anti-oxidant.
  • Anti-oxidants are able to inhibit or prevent the undesired changes in the compositions to be protected caused by oxygen effects and other oxidative processes.
  • the effect of the anti-oxidants consists in most cases in them acting as free-radical scavengers for the free radicals which arise during autoxidation.
  • Anti-oxidants can for example be selected from the group consisting of
  • the anti-oxidant is selected from the group consisting of pentaerythrityl, tetra-di-t-butyl hydroxyhydrocinnamate, nordihydroguaiaretic acid, ferulic acid, resveratrol, propyl gallate, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), ascorbyl palmitate and tocopherol.
  • compositions according to the invention can comprise the anti-oxidants in an amount of 0.001 to 25 wt.-%, preferably 0.005 to 10 wt.-%, preferably 0.01 to 8 wt.-%, preferably 0.025 to 7 wt.-%, preferably 0.05 to 5 wt.-%, based on the total weight of the composition.
  • One embodiment of the invention is directed to a composition
  • a composition comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, and at least one deodorant-active agent.
  • the non-canonical terpene or terpenoid, the stereoisomer thereof, the mixture of different stereoisomers thereof or the mixture of different non-canonical terpenes and/or terpenoids can be used to impart a clean, long-lasting note to deodorizing compositions as well as to the skin treated with such compositions.
  • Deodorizing compositions counteract, mask or eliminate body odors.
  • Body odors are formed through the action of skin bacteria on apocrine perspiration which results in the formation of unpleasant-smelling degradation products.
  • the at least one deodorant-active agent is selected from the groups consisting of anti-perspirants, esterase inhibitors and antibacterial agents.
  • Suitable antiperspirants can be selected from the group consisting of salts of aluminium, zirconium or zinc.
  • Examples are aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrate and complex compounds thereof, for example with 1,2-propylene glycol, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof, for example with amino acids, such as glycine.
  • Aluminium chlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex compounds thereof are preferably used.
  • compositions comprise at least one antiperspirant selected from the group consisting aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohydrate, aluminium hydroxyallantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate and aluminium zirconium pentachlorohydrate
  • compositions according to the invention can comprise the antiperspirants in an amount of 1 to 50, preferably 5 to 30 and more particularly 10 to 25 wt.-%, based on the solids content of the composition.
  • esterase inhibitors are for example trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate.
  • Esterase inhibitors inhibit enzyme activity and thus reduce odor formation. The free acid is probably released by the cleavage of the citric acid ester and reduces the pH value of the skin to such an extent that the enzymes are inactivated by acylation.
  • esterase inhibitors are sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid and malonic acid diethyl ester, hydroxycarboxylic acids and esters thereof, for example citric acid, malic acid, tartaric acid or tartaric acid diethyl ester, and zinc glycinate.
  • dicarboxylic acids and esters thereof for example glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid dieth
  • compositions comprise at least one esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol, sitosterol sulfate, sitosterol phosphate, glutaric acid, glutaric acid monoethyl ester, glutaric acid diethyl ester, adipic acid, adipic acid monoethyl ester, adipic acid diethyl ester, malonic acid, malonic acid diethyl ester, citric acid, malic acid, tartaric acid, tartaric acid diethyl ester and zinc glycinate.
  • esterase inhibitor selected from the group consisting of trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate triethyl citrate, lanosterol, cholesterol, campesterol, stigmasterol,
  • compositions according to the invention can comprise the esterase inhibitors in amounts of 0.01 to 20, preferably 0.1 to 10 and more particularly 0.5 to 5 wt.-%, based on the solids content of the composition.
  • anti-bacterial agents encompasses substances which have bactericidal and/or bacteriostatic properties. Typically these substances act against gram-positive bacteria such as, for example, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate
  • the antibacterial agent is selected from the group consisting of chitosan, phenoxyethanol, 5-chloro-2-(2,4-dichlorophenoxy)-phenol, 4-hydroxybenzoic acid and salts and esters thereof, N-(4-chlorophenyl)-N'-(3,4-dichlorophenyl)-urea, 2,4,4'-trichloro-2'-hydroxydiphenylether (triclosan), 4-chloro-3,5-dimethylphenol, 2,2'-methylene-bis-(6-bromo-4-chlorophenol), 3-methyl-4-(1-methylethyl)-phenol, 2-benzyl-4-chlorophenol, 3-(4-chlorophenoxy)-propane-1,2-diol, 3-iodo-2-propinyl butyl carbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), phenoxyethanol, glycerol monocaprate,
  • compositions according to the invention can comprise the antibacterial agents in amounts of 0.01 to 5 wt.% and preferably 0.1 to 2 wt.-%, based on the solids content of the composition.
  • compositions according to the invention can further comprise one or more substances, such as, for example: preservatives, abrasives, anti-acne agents, agents to combat skin aging, anti-cellulite agents, antidandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-alleviating agents, astringents, sweat-inhibiting agents, antiseptics, anti-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, care agents, hair removal agents, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair smoothing agents, moisture-donating agents, moisturizing substances, humectant substances, bleaching agents, strengthening agents, stain removal agents, optical brighteners, impregnating agents, soil repellents, friction-reducing agents, lubricants, moistur
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof and the mixtures of different non-canonical terpenes and/or terpenoids, as described herein, can be used in a wide range of compositions, preferably in aroma compositions, more preferably in fragrance compositions.
  • the olfactory properties and the substance properties (such as solubility in customary solvents and compatibility with further customary constituents of such compositions) of the non-canonical terpenes or terpenoids underline the particular suitability of the combinations for the stated use purposes and compositions.
  • Suitable compositions are for example perfume compositions, body care compositions (including cosmetic compositions), products for oral and dental hygiene, hygiene articles, cleaning compositions (including dishwashing compositions), textile detergent compositions, compositions for scent dispensers, foods, food supplements, pharmaceutical compositions and crop protection compositions.
  • Perfume compositions can be selected from fine fragrances, air fresheners in liquid form, gel-like form or a form applied to a solid carrier, aerosol sprays, scented cleaners, perfume candles and oils, such as lamp oils or oils for massage.
  • Examples for fine fragrances are perfume extracts, Eau de perfumes, Eau de Toilettes, Eau de Colognes, Eau de Solide and Extrait perfume.
  • Body care compositions include cosmetic compositions, and can be selected from after-shaves, pre-shave products, splash colognes, solid and liquid soaps, shower gels, shampoos, shaving soaps, shaving foams, bath oils, cosmetic emulsions of the oil-in-water type, of the water-in-oil type and of the water-in-oil-in-water type, such as e.g. skin creams and lotions, face creams and lotions, sunscreen creams and lotions, after-sun creams and lotions, hand creams and lotions, foot creams and lotions, hair removal creams and lotions, after-shave creams and lotions, tanning creams and lotions, hair care products such as e.g.
  • hairsprays hair gels, setting hair lotions, hair conditioners, hair shampoo, permanent and semi-permanent hair colorants, hair shaping compositions such as cold waves and hair smoothing compositions, hair tonics, hair creams and hair lotions, deodorants and antiperspirants such as e.g. underarm sprays, roll-ons, deodorant sticks and deodorant creams, products of decorative cosmetics such as e.g. eye-liners, eye-shadows, nail varnishes, make-ups, lipsticks and mascara.
  • decorative cosmetics such as e.g. eye-liners, eye-shadows, nail varnishes, make-ups, lipsticks and mascara.
  • Products for oral and dental hygiene can be selected from toothpaste, dental floss, mouth wash, breath fresheners, dental foam, dental gels and dental strips.
  • Hygiene articles can be selected from joss sticks, insecticides, repellents, propellants, rust removers, perfumed freshening wipes, armpit pads, baby diapers, sanitary towels, toilet paper, cosmetic wipes, pocket tissues, dishwasher and deodorizer.
  • Cleaning compositions such as e.g. cleaners for solid surfaces
  • perfumed acidic, alkaline and neutral cleaners such as e.g. floor cleaners, window cleaners, dishwashing compositions both for handwashing and machine washing use, bath and sanitary cleaners, scouring milk, solid and liquid toilet cleaners, powder and foam carpet cleaners, waxes and polishes such as furniture polishes, floor waxes, shoe creams
  • Textile detergent compositions can be selected from liquid detergents, powder detergents, laundry pretreatments such as bleaches, soaking agents and stain removers, fabric softeners, washing soaps, washing tablets.
  • Food means a raw, cooked, or processed edible substance, ice, beverage or ingredient used or intended for use in whole or in part for human consumption, or chewing gum, gummies, jellies, and confectionaries.
  • a food supplement is a product intended for ingestion that contains a dietary ingredient intended to add further nutritional value to the diet.
  • a dietary ingredient may be one, or any combination, of the following substances: a vitamin, a mineral, an herb or other botanical, an amino acid, a dietary substance for use by people to supplement the diet by increasing the total dietary intake, a concentrate, metabolite, constituent, or extract.
  • Food supplements may be found in many forms such as tablets, capsules, softgels, gelcaps, liquids, or powders.
  • compositions comprise compositions which are intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease as well as articles (other than food) intended to affect the structure or any function of the body of man or other animals.
  • Crop protection compositions comprise compositions which are intended for the managing of plant diseases, weeds and other pests (both vertebrate and invertebrate) that damage agricultural crops and forestry.
  • compositions according to the invention can further comprise one or more substances, such as, for example: preservatives, abrasives, anti-acne agents, agents to combat skin aging, antibacterial agents, anti-cellulite agents, antidandruff agents, anti-inflammatory agents, irritation-preventing agents, irritation-alleviating agents, antimicrobial agents, antioxidants, astringents, sweat-inhibiting agents, antiseptics, anti-statics, binders, buffers, carrier materials, chelating agents, cell stimulants, cleaning agents, care agents, hair removal agents, surface-active substances, deodorizing agents, antiperspirants, emulsifiers, enzymes, essential oils, fibers, film formers, fixatives, foam formers, foam stabilizers, substances for preventing foaming, foam boosters, fungicides, gelling agents, gel-forming agents, hair care agents, hair shaping agents, hair smoothing agents, moisture-donating agents, moisturizing substances, humectant substances, bleaching agents, strengthening agents, stain removal
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof and the mixtures of different non-canonical terpenes and/or terpenoids may be worked into in compositions simply by directly mixing them with the basic composition lacking only this/these compound(s).
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof or the mixtures of different non-canonical terpenes and/or terpenoids may be mixed simultaneously or consecutively with the other components of the composition or with pre-formed mixtures of a part of the other components.
  • the non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof or the mixtures of different non-canonical terpenes and/or terpenoids may, in an earlier step, be entrapped with an entrapment material, for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or may be chemically bonded to substrates, which are adapted to release said non-canonical terpenes or terpenoids upon application of an external stimulus such as light, enzyme, or the like, and then mixed with the composition.
  • an entrapment material for example, polymers, capsules, microcapsules and nanocapsules, liposomes, film formers, absorbents such as carbon or zeolites, cyclic oligosaccharides and mixtures thereof, or may be
  • non-canonical terpenes or terpenoids, the stereoisomers thereof, the mixtures of different stereoisomers thereof or the mixtures of different non-canonical terpenes and/or terpenoids and compositions comprising these compounds can also be in mi-croencapsulated form, spray-dried form, in the form of inclusion complexes or in the form of extrusion products.
  • the properties can be further optimized by so-called "coating" with suitable materials with regard to a more targeted release of the scent, for which purpose preferably waxy synthetic substances such as e.g. polyvinyl alcohol are used.
  • the microencapsulation can take place for example by the so-called coacervation method with the help of capsule materials, e.g. made of polyurethane-like substances or soft gelatin.
  • the spray-dried perfume oils can be produced for example by spray-drying an emulsion or dispersion comprising a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, or a composition of the present invention described herein, wherein carrier substances that can be used are modified starches, proteins, dextrin and vegetable gums.
  • Inclusion complexes can be prepared e.g.
  • Extrusion products can be produced by melting a non-canonical terpene or terpenoid or a stereoisomer thereof or a mixture of different stereoisomers thereof or a mixture of different non-canonical terpenes and/or terpenoids, or a composition of the present invention described herein with a suitable wax-like substance and by extrusion with subsequent solidification, optionally in a suitable solvent, e.g. isopropanol.
  • a suitable solvent e.g. isopropanol.
  • the total amount of the one or more non-canonical terpene or terpenoid in the compositions according to the present invention is typically adapted to the particular intended use or the intended application and can, thus, vary over a wide range.
  • the customary standard commercial amounts for scents are used.
  • compositions according to the invention can comprise the non-canonical terpene or terpenoid in an overall amount of from 0.001 to 99.9% by weight, preferably from 0.01 to 90% by weight, more preferably from 0.05 to 80%, in particular from 0.1 to 60% by weight, more particularly from 0.1 to 40% by weight, e.g. from 0.1 to 10% by weight or 0.1 to 15% by weight, based on the total weight of the composition.
  • the compositions comprise the non-canonical terpene or terpenoid in an overall amount of from 0.001 to 5 weight%, preferably from 0.01 to 2 weight% based on the total weight of the composition.
  • the non-canonical terpenes and terpenoids not only have a pleasant aroma, especially fragrance; they are also readily available. In particular they can be readily produced with a reduced CO 2 footprint, e.g. by using renewable sources.
  • scent strip tests were performed.
  • Fragrance composition 3 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution B.
  • Fragrance composition 4 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution B.
  • Fragrance composition 5 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution B.
  • Fragrance composition 6 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution B.
  • Fragrance composition 7 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution C.
  • Fragrance composition 8 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution C.
  • Fragrance composition 9 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution C.
  • Fragrance composition 10 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution C.
  • Fragrance composition 11 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution D.
  • Fragrance composition 12 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution D.
  • Fragrance composition 13 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution D.
  • Fragrance composition 14 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution D.
  • Fragrance composition 15 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution E.
  • Fragrance composition 16 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution E.
  • Fragrance composition 17 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution E.
  • Fragrance composition 18 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution E.
  • Fragrance composition 19 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution F.
  • Fragrance composition 20 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution F.
  • Fragrance composition 21 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution F.
  • Fragrance composition 22 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution F.
  • Fragrance composition 23 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution G.
  • Fragrance composition 24 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution G.
  • Fragrance composition 25 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution G.
  • Fragrance composition 26 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution G.
  • Fragrance composition 27 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution H.
  • Fragrance composition 28 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution H.
  • Fragrance composition 29 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution H.
  • Fragrance composition 30 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution H.
  • Fragrance composition 31 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution I.
  • Fragrance composition 32 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution I.
  • Fragrance composition 33 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution I.
  • Fragrance composition 34 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution I.
  • Fragrance composition 35 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution J.
  • Fragrance composition 36 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution J.
  • Fragrance composition 37 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution J.
  • Fragrance composition 38 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution J.
  • Fragrance composition 39 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution K.
  • Fragrance composition 40 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution K.
  • Fragrance composition 41 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution K.
  • Fragrance composition 42 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution K.
  • Fragrance composition 43 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution L.
  • Fragrance composition 44 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution L.
  • Fragrance composition 45 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution L.
  • Fragrance composition 46 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution L.
  • Fragrance composition 47 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution M.
  • Fragrance composition 48 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution M.
  • Fragrance composition 49 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution M.
  • Fragrance composition 50 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution M.
  • Fragrance composition 51 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution N.
  • Fragrance composition 52 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution N.
  • Fragrance composition 53 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution N.
  • Fragrance composition 54 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution N.
  • Fragrance composition 55 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution O.
  • Fragrance composition 56 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution O.
  • Fragrance composition 57 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution O.
  • Fragrance composition 58 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution O.
  • Fragrance composition 59 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution P.
  • Fragrance composition 60 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution P.
  • Fragrance composition 61 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution P.
  • Fragrance composition 62 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution P.
  • Fragrance composition 63 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution Q.
  • Fragrance composition 64 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution Q.
  • Fragrance composition 65 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution Q.
  • Fragrance composition 66 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution Q.
  • Fragrance composition 67 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution R.
  • Fragrance composition 68 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution R.
  • Fragrance composition 69 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution R.
  • Fragrance composition 70 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution R.
  • Fragrance composition 71 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution S.
  • Fragrance composition 72 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution S.
  • Fragrance composition 73 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution S.
  • Fragrance composition 74 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution S.
  • Fragrance composition 75 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution T.
  • Fragrance composition 76 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution T.
  • Fragrance composition 77 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution T.
  • Fragrance composition 78 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution T.
  • Fragrance composition 79 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution U.
  • Fragrance composition 80 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution U.
  • Fragrance composition 81 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution U.
  • Fragrance composition 82 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution U.
  • Fragrance composition 83 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution V.
  • Fragrance composition 84 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution V.
  • Fragrance composition 85 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution V.
  • Fragrance composition 86 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution V.
  • Fragrance composition 87 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution W.
  • Fragrance composition 88 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution W.
  • Fragrance composition 89 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution W.
  • Fragrance composition 90 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution W.
  • Fragrance composition 91 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution X.
  • Fragrance composition 92 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution X.
  • Fragrance composition 93 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution X.
  • Fragrance composition 94 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution X.
  • Fragrance composition 95 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution Y.
  • Fragrance composition 96 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution Y.
  • Fragrance composition 97 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution Y.
  • Fragrance composition 98 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution Y.
  • Fragrance composition 99 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution Z.
  • Fragrance composition 100 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution Z.
  • Fragrance composition 101 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution Z.
  • Fragrance composition 102 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution Z.
  • Fragrance composition 103 corresponds to fragrance composition 1A, where Solution A is replaced by the same amount of Solution AA.
  • Fragrance composition 104 corresponds to fragrance composition 1B, where Solution A is replaced by the same amount of Solution AA.
  • Fragrance composition 105 corresponds to fragrance composition 2A, where Solution A is replaced by the same amount of Solution AA.
  • Fragrance composition 106 corresponds to fragrance composition 2B, where Solution A is replaced by the same amount of Solution AA.
  • compositions according to tables 2 and table 3, namely 1A, 1B, 2A and 2B as well as fragrance compositions 3to 106 could be included in various compositions selected from the group consisting of deo pump spray, clean hair-conditioner, face wash gel, foam bath concentrate, hair gel, self-foaming bodywash, sprayable sun care emulsion, sprayable sun protection emulsion, emollient facial gel, 2-phases oil foam bath, shampoos, shower bath, hydro-alcoholic AP/deo pump spray, aerosol, aqueous/alcoholic AP/deo roll-on, styling gel type "Out of Bed", shaving foam, sensitive skin baby shampoo, body wash for sensitive skin, gloss enhancing shampoo for sensitive scalp, deo stick, baby wipe, after shave balm, face gel, face day care cream, face cleanser, body lotion, sun care SPF50+, sprayable lotion, hand dish cleaner - regular, hand dish cleaner - concentrate, sanitary cleaner - concentrate, all-purpose cleaner, anti-bacterial fabric softener, detergent composition, powder detergent
  • Compositions 1A, 1B, 2A, 2B and 3to 106 can for example be formulated in specific formulations as disclosed in IP.com Number: IPCOM000258614D entitled New Aroma Chemicals pages 6 to 46, Table 1 to Table D13, wherein the "Fragrance Composition 1A" is replaced by identical amounts of compositions 1A, 1B, 2A, 2B and 3 to 106.

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  • Fats And Perfumes (AREA)
EP22174377.6A 2022-05-19 2022-05-19 Utilisation de terpènes ou terpénoïdes non canoniques comme substances chimiques aromatiques Withdrawn EP4279568A1 (fr)

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US20210139811A1 (en) * 2019-11-08 2021-05-13 Bedoukian Research, Inc. Compositions containing fenchols and methods of use
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GB814636A (en) * 1956-07-30 1959-06-10 Hoffmann La Roche Novel unsaturated alcohols and esters thereof and a process for the manufacture of same
US20110266361A1 (en) * 2008-12-30 2011-11-03 Basf Se Pheromone dispenser
WO2014114733A1 (fr) * 2013-01-25 2014-07-31 Basf Se Utilisation de 4,8-diméthyl-3,7-nonadién-2-ol comme substance odorante
US20180187123A1 (en) * 2015-09-24 2018-07-05 Givaudan Sa Perfume Compositions
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WO2021198525A1 (fr) * 2020-04-02 2021-10-07 Givaudan Sa (s,z)-3,7-diméthylnon-6-én-1-ol et son utilisation comme parfum
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C. IGNEA ET AL., NAT. CHEM. BIOL., vol. 14, 2018, pages 1090 - 1098
K. BAUER, D. GARBEH. SURBURG: "Common Fragrance and Flavor Materials", vol. 4th, 2001, WILEY- VCH
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