WO2023199324A1 - Mélange d'isomères d'ester 3-hexényle et ses utilisations - Google Patents

Mélange d'isomères d'ester 3-hexényle et ses utilisations Download PDF

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WO2023199324A1
WO2023199324A1 PCT/IL2023/050391 IL2023050391W WO2023199324A1 WO 2023199324 A1 WO2023199324 A1 WO 2023199324A1 IL 2023050391 W IL2023050391 W IL 2023050391W WO 2023199324 A1 WO2023199324 A1 WO 2023199324A1
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Prior art keywords
hexen
cis
odor
trans
salicylate
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Inventor
Ad Cohen
Maia AIZENMAN
Rotem SELLA-EREZ
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Agan Aroma and Fine Chemicals Ltd
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Agan Aroma and Fine Chemicals Ltd
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
    • A23L27/2028—Carboxy compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • 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

Definitions

  • the present invention relates to odoriferous and/or flavourous substances, and more particularly to novel odoriferous and/or flavourous mixture of ester of czs- 3 -hexenyl and ester of trans-3-hexenyl, and to fragrance and/or flavor compositions containing the same.
  • Odoriferous and flavourous substances are widely used in fields such as beverages, cosmetics, sanitary and hygienic goods, detergents, bath refreshing additives, medicines, and agricultural chemicals. Odoriferous substances are used for imparting scent, odor, aroma, or fragrance to the product or to the body.
  • a fragrance results from a combination of a variety of components in a fragrance composition.
  • fragrances are created by blending odoriferous substances, optionally along with carrier and other chemical materials. These materials are blended in order to achieve what are known as substances with “high volatility”, (molecules with high vapor pressure, evaporate quickly, and give the first impression-high volatility), substances with “medium volatility” and substances with “low volatility” components (molecules with relatively low vapor pressure, low volatility, which evaporate slowly and keep the main character of the odor).
  • substances with “high volatility” molecules with high vapor pressure, evaporate quickly, and give the first impression-high volatility
  • substances with “medium volatility” and substances with “low volatility” components molecules with relatively low vapor pressure, low volatility, which evaporate slowly and keep the main character of the odor.
  • the character of the odor often referred to as “odor profile” may change overtime.
  • green odor descriptors are of a particular interest.
  • the fresh aroma of freshly cut green grass fragrance-imparting agents are widely used, for example, in perfumery, candles, potpourri, bath and body products, melt-and-pour soap, cold process soap, gel wax, and the like, and for imparting a grass scent to artificial grass or turf.
  • green odor descriptor-imparting odoriferous substance is cis-3-hexen- l-ol, which is also known as “leaf alcohol”.
  • Other green odor descriptor-imparting agents which are widely used in the industry include, for example, n-hexanal, n-hexanol, trans-2-hexenal, trans- 2-hexen-l-ol, cis-3-hcxcnal, and the corresponding ester derivatives thereof.
  • Leaf alcohol derivatives are a common type of green leaf volatiles (GLVs) and are produced within plant cells during developmental processes or in response to external stress. GLVs are mainly known for controlling plant-plant and plant-herbivore interactions. Ester derivatives of leaf alcohol were also found to act as microbial agents [Lopez-Gresa et al. (2017) Front. Plant Sci. 8, 1188; Scala et al. (2013) Int. J. Mol. Sci. 14(9), 17781-17811], and in some cases it is used as odor and/or food additive.
  • Extracting green-scent imparting substances from green plants and leaves typically involve high production costs and low production amounts and are therefore commercially ineffective.
  • the demand for green odor descriptors has grown to exceed their supply from traditional natural sources such as mint (Mentha arvensis) oil and other plant oils. This has motivated research efforts toward finding alternative ways for obtaining these materials.
  • the present invention is related to a fragrance and/or flavor composition comprising a mixture of esters of trans-3-hexen-l-ol and esters of cis-3-hexen-l-ol.
  • the present invention is related to a process of preparing of said fragrance and/or flavor composition, comprising reaction of the compound of formula I: RCOOR 1 (I) wherein;
  • R is C 2 -C 12 alkyl, C 1 -C 12 alkyl carbonyl, C 2 -C 12 alkenyl, C2-C12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl, optionally interrupted by at least one heteroatom;
  • R 1 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, heteroaryl, arylene, cycloalkyl, optionally interrupted by at least one heteroatom; with a mixture of trans-3-hexen-l-ol present in an amount of from 55 % to 95 % by weight and cis-3-hexen-l-ol, present in amount of from 5 % to 45 % by weight, based on the weight of total mixture, in the presence of an esterification agent, optionally in the presence of a solvent.
  • the present invention is related to a process of preparing of said fragrance and/or flavor composition, comprising reaction of compound of formula II RC(O)OC(O)R 2 (II) wherein;
  • R is C 2 -C 12 alkyl, C 1 -C 12 alkyl carbonyl, C 2 -C 12 alkenyl, C2-C12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl optionally interrupted by at least one heteroatom;
  • R 2 is C 1 -C 6 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl optionally interrupted by at least one heteroatom; with a mixture of trans-3-hexen-l-ol present in an amount of from 55 % to 95 % by weight and cis-3-hexen-l-ol present in an amount of from 5 % to 45 % by weight, based on the weight of total mixture, optionally in the presence of a solvent.
  • the present invention is also related to odor-imparting formulations comprising fragrance and/or flavor composition disclosed herein.
  • the present invention is also related to flavor-imparting formulation comprising fragrance and/or flavor compositions disclosed herein.
  • alkyl refers to a branched, unbranched, or cyclic carbon chain.
  • halogen or “halo” as used herein refers to one or more halogen atoms, defined as F, Cl, Br, and I.
  • hydroxy refers to a hydrogen attached to the parent molecular moiety through an oxygen atom.
  • alkoxy refers to an alkyl group attached to the parent molecular moiety through an oxygen atom.
  • aryloxy refers to an aryl group attached to the parent molecular moiety through an oxygen atom.
  • alkenyl describes an unsaturated aliphatic hydrocarbon end group which comprises at least one carbon-carbon double bond, including straight chain and branched chain groups.
  • the alkenyl group may be substituted or non-substituted.
  • Substituted alkenyl may have one or more substituents, whereby each substituent group can independently be, for example, alkynyl, aryl, heteroaryl, cycloalkyl optionally interrupted by heteroatom atoms, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, and hydrazine.
  • alkynyl describes an unsaturated aliphatic hydrocarbon end group which comprises at least one carbon-carbon triple bond, including straight chain and branched chain groups.
  • the alkynyl group may be substituted or non-substituted.
  • Substituted alkynyl may have one or more substituents, whereby each substituent group can independently be, for example, alkenyl, aryl, heteroaryl, cycloalkyl optionally interrupted by heteroatom atoms, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, and hydrazine.
  • cycloalkyl describes an all-carbon monocyclic or fused ring (i.e., rings which share an adjacent pair of carbon atoms) group where one or more of the rings does not have a completely conjugated pi-electron system.
  • the cycloalkyl group may be substituted or nonsubstituted.
  • Substituted cycloalkyl may have one or more substituents, whereby each substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl optionally interrupted by heteroatom atoms, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, and hydrazine.
  • substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl optionally interrupted by heteroatom atoms, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano
  • the cycloalkyl group can be an end group, as this phrase is defined herein, wherein it is attached to a single adjacent atom, or a linking group, as this phrase is defined herein, connecting two or more moieties.
  • cycloalkyl optionally interrupted by heteroatom atoms means monocyclic or fused carbon atom ring group having in the ring(s) one or more atoms such as nitrogen, oxygen and sulfur. The rings may also have one or more double bonds. However, the rings do not have a completely conjugated pi-electron system.
  • the “cycloalkyl optionally interrupted by heteroatom atoms” may be substituted or nonsubstituted.
  • Substituted cycloalkyl optionally interrupted by heteroatom atoms may have one or more substituents, whereby each substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, hydrazine and cycloalkyl optionally interrupted by heteroatom atoms.
  • substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azi
  • the cycloalkyl optionally interrupted by heteroatom atoms group can be an end group, as this phrase is defined herein, where it is attached to a single adjacent atom, or a linking group, as this phrase is defined herein, connecting two or more moieties.
  • Representative examples are piperidine, piperazine, tetrahydrofuran, tetrahydropyran, morpholine and the like.
  • aryl describes an all-carbon monocyclic or fused-ring polycyclic (i.e., rings which share adjacent pairs of carbon atoms) end group (as this term is defined herein) having a completely conjugated pi-electron system.
  • the aryl group may be substituted or non-substituted.
  • Substituted aryl may have one or more substituents, whereby each substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, hydrazine and cycloalkyl optionally interrupted by heteroatom atoms.
  • Phenyl and naphthyl are representative aryl end groups.
  • heteroaryl describes a monocyclic or fused carbon-based ring (i.e., rings which share an adjacent pair of atoms) having in the ring(s) one or more heteroatoms, such as, for example, nitrogen, oxygen and sulfur and, in addition, having a completely conjugated pi-electron system.
  • heteroaryl groups include pyrrole, furan, thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrimidine, quinoline, isoquinoline and purine.
  • the heteroaryl group may be substituted or non-substituted.
  • Substituted heteroaryl may have one or more substituents, whereby each substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy, thiocarbamate, urea, thiourea, carbamate, amide, hydrazine and cycloalkyl optionally interrupted by heteroatom atoms.
  • substituent group can independently be, for example, alkyl, alkenyl, alkynyl, aryl, heteroaryl, amine, halide, sulfonate, sulfoxide, phosphonate, hydroxy, alkoxy, aryloxy, cyano, nitro, azo, azide, sulfonamide, carboxy,
  • the heteroaryl group can be an end group, as this phrase is defined herein, where it is attached to a single adjacent atom, or a linking group, as this phrase is defined herein, connecting two or more moieties.
  • Representative examples are pyridine, pyrrole, oxazole, indole, purine and the like.
  • arylene is a group derived from an aromatic hydrocarbon by removal of a hydrogen atom from each of two carbon atoms of the aryl nucleus, such as, for example, Furan, Pyrrole, Thiophene, Indole, Benzofuran, Carbazole, Quinoline, Isoquinoline, Imidazole, Oxazole, Pyrazole, Pyridazine, Pyrimidine and Purine. It is appreciated that certain features of the invention, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment.
  • salts refers to organic salts such as chloride, bromide, fluoride, iodide, acetate, hydrogen sulfates, phosphates, formats, nitrate, carbonate etc., or, if applicable, alkaline metal salts such as sodium, potassium, calcium, lithium, cesium, magnesium, barium and the like.
  • each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques. In an embodiment, use of the term “about” herein specifically includes ⁇ 10% from the indicated values in the range.
  • the endpoints of all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges.
  • odoriferous substance describes a chemical substance or a mixture of chemical substances featuring an odor which is commonly conceived as pleasant.
  • odor descriptor and “odor profiles” described herein, such as “green”, “floral”, “sweet”, “soapy-like”, etc., are well defined by the Dravnieks atlas (ASTM publication code number 05-061000-36).
  • descriptive analysis refers to a sensory methodology utilizing a panel of trained assessors to identify and describe specific sensory attributes, also called “descriptors”.
  • flavourous substances any odoriferous description and use of these disclosed mixtures herein can also be acknowledged as flavourous description and can be use in flavourous applications.
  • the present invention provides a fragrance and/or flavor composition comprising a mixture of esters of trans-3-hexen-l-ol and esters of cis-3-hexen-l-ol.
  • a fragrance and/or flavor composition comprises a mixture of the same esters of trans-3-hexen-l-ol and the cis-3-hexen-l-ol derived from a particular carboxylic acid.
  • a fragrance and/or flavor composition comprises a mixture of the same esters of trans-3-hexen-l-ol and cis-3-hexen-l -ol, derived from a particular organic anhydride.
  • a fragrance and/or flavor composition comprises a mixture of the same esters of trans-3-hexen-l-ol and cis-3-hexen-l-ol, derived from a particular organic ester.
  • the present invention provides a fragrance and/or flavor composition comprising a mixture of an ester of trans-3-hexen-l-ol in an amount of from 55 % to 95 % by weight and an ester of cis-3-hexen-l-ol in an amount of from 5 % to 45 % based on the weight of the total composition.
  • the present invention provides a fragrance and/or flavor composition
  • a fragrance and/or flavor composition comprising a mixture of an ester of trans-3-hexen-l-ol in an amount of from 60 % to 90 % by weight of the total mixture and an ester of cis-3-hexen-l-ol in an amount of from 10 % to 40 % based on the weight of the total composition.
  • the present invention provides a fragrance and/or flavor composition
  • a fragrance and/or flavor composition comprising a mixture of an ester of trans-3-hexen-l-ol in an amount of from 65 % to 85 % by weight of the total mixture and an ester of cis-3-hexen-l-ol in an amount of from 15 % to 35 % based on the weight of the total composition.
  • the present invention provides a fragrance and/or flavor composition
  • a fragrance and/or flavor composition comprising a mixture of an ester of trans-3-hexen-l-ol in an amount of from 67 % to 82 % by weight of the total mixture and an ester of cis-3-hexen-l-ol in an amount of from 18 % to 33 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprising a mixture of an ester of trans-3-hexen-l-ol in an amount of from 70 % to 80 % by weight of the total mixture and an ester of cis-3-hexen-l-ol in an amount of from 20 % to 30 % based on the weight of the total composition.
  • the weight ratio of the ester of trans-3-hexen- l-ol to the ester of cis-3-hexen-l-ol in the mixture is in a range of from about 9.5:0.5 to 5.5:4.5.
  • the weight ratio of the ester of trans-3-hexen- l-ol to the ester of cis-3-hexen-l-ol in the mixture is in a range of from about 9.5:0.5 to 5.5:4.5.
  • the weight ratio of the ester of trans-3-hexen- l-ol to the ester of cis-3-hexen-l-ol in the mixture is in a range of from about 9:1 to 6:4.
  • the weight ratio of the ester of trans-3-hexen- l-ol to the ester of cis-3-hexen-l-ol in the mixture is in a range of from about 8.5:2.5 to 6.5:4.5.
  • the weight ratio of the ester of trans-3-hcxcn-l -ol to the ester of cis- 3-hexen-l-ol in the mixture is in a range of from about 8:2 to 7:3.
  • the fragrance and/or flavor composition of the ester of trans- 3-hexen-l-ol and the ester of cis-3-hexen- 1 -ol, disclosed herein, features alike odor profile of the corresponding ester of the cis-3-hexen-l-ol.
  • the fragrance and/or flavor composition of the ester of trans- 3-hexen-l-ol and the ester of cis-3-hexen-l-ol, disclosed herein features an odor profile, that differs from the ester of the cis-3-hexen-l-ol by at least one odor descriptor.
  • the fragrance and/or flavor composition of the ester of trans- 3-hexen-l-ol and the ester of cis-3-hexen-l-ol, disclosed herein features an odor profile, that differs from the ester of the cis-3-hexen-l-ol by at least two odor descriptors.
  • the fragrance and/or flavor composition of the ester of trans- 3-hexen-l-ol and the ester of cis-3-hexen-l-ol, disclosed herein features an odor profile, that differs from the ester of the cis-3-hexen-l-ol by at least three odor descriptors.
  • the odor descriptor is selected from a group comprising floral, citrus, fruity, aquatic, spicy, edible, animalic, green, woody, earthy, amber, aldehydes, balsamic, mecanicy, grain, herbaceous, mineral, mossy, musk, oriental, resinous, smokey, textile, tobacco odor.
  • the odor descriptor is selected from a group comprising fresh, rose, mushroom, coconut, soapy, jasmine, lavender, lilies, violets, lilacs, orange, clementine, lemon, grapefruit, lime, apple, pineapple, berries, peach, lychee, cascalone, seaweed, seawater, cucumber, coral reef, cinnamon, cloves, coffee, ginger, coriander, saffron, mushroom, nutmeg, cotton candy, sweets, coca-cola, bubble gum, lemonade, caramel, musk, amber, civet, leather, goat hair, truffle, basil, mint, green tea, aloe vera, cilantro, fern, cedar, bamboo, sandalwood, eucalyptus, pine tree, agarwood (oud), vetiver, patchouli, labdanum, hay, dew like, powdery, amber, ambreine, aquatic, balsamic, cologne, fresh, green, anise, lavender, cham
  • the fragrance and/or flavor composition of an ester of trans- 3-hexen-l-ol and an ester of cis-3-hexen-l-ol, disclosed herein features an odor descriptor, that differs from the ester of the cis-3-hexen-l-ol by at least one score.
  • the fragrance and/or flavor composition of an ester of trans- 3-hexen-l-ol and an ester of cis-3-hexen-l-ol, disclosed herein features an odor descriptor, that differs from the ester of the cis-3-hexen-l-ol by at least two scores.
  • the fragrance and/or flavor composition of an ester of trans- 3-hexen-l-ol and an ester of cis-3-hexen-l-ol, disclosed herein features an odor descriptor, that differs from the ester of the cis-3-hexen-l-ol by at least three scores.
  • the ester of trans-3-hexen-l-ol and/or cis-3-hexen-l-ol is selected from a group comprising: acetate, salicylate, propionate, cyclopropionate, tiglate, isobutyrate, butyrate, 2-methyl butyrate, 2-methyl butanoate, 3 -methyl butanoate, benzoate, aminobenzoate, anthranilate, crotonate, phenyl acetate, 2-methyl-2-pentenoate, hexanoate, heptanoate, octanoate, nonanoate, decanoate, formate, isovalerate, lactate, levulinate, nicotinate, pyruvate, valerate, anisate, caproate, caprylate, cinnamate, dihydrocinnamate, palmitate, pivalate, senecioate, oct-2-ynoate, 5-
  • the ester is acetate
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl acetate in an amount of from 55 % to 95 % by weight and cis-3-hexen-l-yl acetate in an amount of from 5 % to 45 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans- 3 -hexen-l-yl acetate in an amount of from 60 % to 90 % by weight and cis-3 -hexen-l-yl acetate in an amount of from 10 % to 40 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans- 3 -hexen-l-yl acetate in an amount of from 65 % to 85 % by weight and cis-3 -hexen-l-yl acetate in an amount of from 15 % to 35 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans- 3 -hexen-l-yl acetate in an amount of from 67 % to 82 % by weight and cis-3 -hexen-l-yl acetate in an amount of from 18 % to 33 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans- 3 -hexen-l-yl acetate in an amount of from 70 % to 80 % by weight and cis-3 -hexen-l-yl acetate in an amount of from 20 % to 30 % based on the weight of the total composition.
  • the weight ratio of trans-3 -hexen-l-yl acetate to cis-3- hexen-l-yl acetate is from 9.5:0.5 to 5.5:4.5.
  • the weight ratio of trans-3 -hexen-l-yl acetate to cis-3- hexen-l-yl acetate is from 9:1 to 6:4.
  • the weight ratio of trans-3 -hexen-l-yl acetate to cis-3- hexen-l-yl acetate is from 6.5:4.5 to 8.5:2.5.
  • the weight ratio of trans-3 -hexen-l-yl acetate to cis-3- hexen-l-yl acetate is from 8:2 to 7:3.
  • the fragrance and/or flavor composition of trans-3 -hexen-l- yl acetate and of cis-3 -hexen-l-yl acetate featuring odor descriptors of floral, green, herbal, aromatic, sweet, dew like and fruity.
  • the fragrance and/or flavor composition of trans-3 -hexen-l- yl acetate and cis-3-hexen-l-yl acetate features an odor profile, that differs from cis-3 -hexen-l-yl acetate by at least one odor descriptor.
  • the fragrance and/or flavor composition of trans-3 -hexen-l- yl acetate and cis-3-hexen-l-yl acetate features an odor profile, that differs from the ester of cis-3-hexen-l-yl acetate by at least two odor descriptors.
  • the fragrance and/or flavor composition of trans-3 -hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features an odor profile, that differs from the ester of cis-3-hexen-l-yl acetate by at least three odor descriptors.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a green odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least four odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a green odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least three odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a green odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least two odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a sweet odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least four odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a sweet odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least three odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a sweet odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least two odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a fruity odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least four odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a fruity odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least three odor scores.
  • the fragrance and/or flavor composition of trans-3-hexen-l- yl acetate and cis-3-hexen-l-yl acetate, disclosed herein features a fruity odor descriptor, that differs from cis-3-hexen-l-yl acetate by at least two odor scores.
  • the ester is salicylate.
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl salicylate in an amount of from 55 % to 95 % by weight and cis-3-hexen-l- yl salicylate in an amount of from 5 % to 45 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl salicylate in an amount of from 60 % to 90 % by weight and cis-3-hexen-l- yl salicylate in an amount of from 10 % to 40 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl salicylate in an amount of from 65 % to 85 % by weight and cis-3-hexen-l- yl salicylate in an amount of from 15 % to 35 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl salicylate in an amount of from 67 % to 82 % by weight and cis-3-hexen-l- yl salicylate in an amount of from 18 % to 33 % based on the weight of the total composition.
  • the fragrance and/or flavor composition comprises a mixture of trans-3-hexen-l-yl salicylate in an amount of from 70 % to 80 % by weight and cis-3-hexen-l- yl salicylate in an amount of from 20 % to 30 % based on the weight of the total composition.
  • the weight ratio of trans-3-hexen-l-yl salicylate to cis-3- hexen-l-yl salicylate is from 9.5:0.5 to 5.5:4.5.
  • the weight ratio of trans-3-hexen-l-yl salicylate to cis-3- hexen-l-yl salicylate is from 9:1 to 6:4.
  • the weight ratio of trans-3-hexen-l-yl salicylate to cis-3- hexen-l-yl salicylate is from 6.5:4.5 to 8.5:2.5.
  • the weight ratio of trans-3-hexen-l-yl salicylate to cis-3- hexen-l-yl salicylate is from 8:2 to 7:3.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and of cis-3-hexen-l-yl salicylate featuring odor descriptors of floral, herbal, powdery, coconut-like and soapy.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features alike odor profile, of cis-3- hexen-l-yl salicylate.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an odor profile, that differs from cis-3-hexen-l-yl salicylate by at least one odor descriptor.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an odor profile, that differs from cis-3-hexen-l-yl salicylate by at least one odor descriptor.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an odor profile, that differs from the ester of cis-3-hexen-l-yl salicylate by at least two odor descriptors.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an odor profile, that differs from the ester of cis-3-hexen-l-yl salicylate by at least three odor descriptors.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least three odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least two odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least one odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an herbal odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least three odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features an herbal odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least two odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l- yl salicylate and cis-3-hexen-l-yl salicylate features an herbal odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least one odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a coconut-like odor descriptor, that differs from cis-3-hexen-l -yl salicylate by at least three odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a coconut-like odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least two odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a coconut-like odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least one odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate, disclosed herein features a powdery odor descriptor, that differs from cis-3-hexen-l -yl salicylate by at least three odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a powdery odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least two odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a powdery odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least one odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least three odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least two odor scores.
  • a fragrance and/or flavor composition of trans-3-hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate features a floral odor descriptor, that differs from cis-3-hexen-l-yl salicylate by at least one odor scores.
  • the present invention provides a process of preparing of fragrance or flavor composition comprising reaction of compound of formula I RCOOR 1 (I) wherein;
  • R is C 2 -C 12 alkyl, C 1 -C 12 alkyl carbonyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl, optionally interrupted by at least one heteroatom;
  • R 1 is hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, aryl, heteroaryl, arylene, cycloalkyl, optionally interrupted by at least one heteroatom; with a mixture of trans-3-hexen-l-ol present in an amount of from 55 % to 95 % by weight and cis-3-hexen-l-ol present in an amount of from 5 % to 45 % by weight, based on the weight of total mixture, in the presence of an esterification agent, optionally in the presence of a solvent.
  • the compound of formula (I) is selected from the group comprising acetic acid, salicylic acid, propionic acid, cyclopropionic acid, tiglic acid, isobutyric acid, butyric acid, 2-methyl butyric acid, 2-methyl butanoic acid, 3-methyl butanoic acid, benzoic acid, aminobenzoic acid, anthranilic acid, crotonic acid, phenyl acetic acid, 2-methyl-2-pentenoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, formic acid, isovaleric acid, lactic acid, levulinic acid, nicotinic acid, pyruvic acid, valeric acid, anisic acid, caproic acid, caprylic acid, cinnamic acid, dihydrocinnamic acid, palmitic acid, pivalic acid, senecioic acid, tiglic acid,
  • the compound of formula (I) is acetic acid.
  • the compound of formula (I) is salicylic acid. According to an embodiment, the compound of formula (I) is ethyl acetate. According to an embodiment, the compound of formula (I) is methyl salicylate.
  • the molar ratio between the mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol to the compound of formula (I) is from about 1:0.1 to 1:20, from about 1:0.5 to 1:10, preferably from about 1:0.5 to 1:5, most preferably from about 1:0.8 to 1:1.5.
  • the esterification agent is selected form a group comprising: sulfuric acid, p-toluenesulfonic, methanesulfonic acid, methanesulfonyl chloride, 4- hydroxybenzenesulfonic acid, dodecylbenzenesulfonic acid, trimethylsilyl triflate, phosphoric acid, dibutyltin oxide, dioctyltin oxide, calcium oxide, magnesium oxide, titanium isopropoxide, 4-(dimethylamino)pyridine, potassium carbonate, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium bisulfate, potassium hydroxide, sodium methoxide, sodium ethoxide, alumina, sodium bisulfate, ammonium chloride, triethylamine, pyridine, imidazole, diisopropylethylamine, acetic acid, acetic anhydride, trifluoroacetic acid, thionyl chloride, tos
  • the esterification agent is sulfuric acid.
  • the esterification agent is p-toluenesulfonic.
  • the esterification agent is methanesulfonic acid.
  • the esterification agent is dibutyltin oxide.
  • the esterification agent is dibutyltin diacetate.
  • the esterification agent is potassium carbonate.
  • the esterification agent is aluminum isopropoxide.
  • the molar ratio between the mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol to the esterification agent is from about 1:0.001 to 1:1, preferably from about 1:0.01 to 1:0.3, most preferably from about 1:0.05 to 1:0.15.
  • the reaction is performed in the presence of a solvent wherein the solvent is selected from a group comprising: water, toluene, dichloromethane, ethyl acetate, tetrahydrofuran, hexane, pentane, dimethylformamide, acetonitrile, dimethyl sulfoxide, diisopropyl ether, acetone, heptane, xylene, m-xylene, pyridine, diethyl ether, benzene, 1,4- dioxane, tert-butyl methyl ether, chloroform, 1,2-dichlorobenzene, octane, chlorobenzene, 1,2- dichloroethane, tert-butyl acetate, cyclohexane, cyclopentyl methyl ether, and the mixtures thereof.
  • the solvent is selected from a group comprising: water, toluene, dichloromethane,
  • the solvent is toluene.
  • solvent is cyclohexane
  • the reaction is performed in the absence of a solvent.
  • the reaction of the mixture of trans-3-hexen-l-ol and cis-3- hexen-l-ol and the compound of formula (I) is performed in the temperature interval of from about 0°C to 130°C.
  • a preferred temperature interval is from about 50°C to 130°C, more preferably from about 110°C to 120°C.
  • the reaction is terminated when the concentration of the mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol is between 0-50%, preferably from 0-10%, most preferably, in particular, when no more than 1% of compound of the mixture of trans-3- hexen-l-ol and cis-3-hcxcn- l -ol remains in the reaction media.
  • reaction mixture containing the product is worked up using common techniques, including, but not limited to: addition of water and/or organic solvent, stirring, cooling, heating, phase separations, distillations, precipitations, recrystallizations, concentrations, filtrations, purifications, pH adjustments, extractions, and drying.
  • the present invention provides a process of preparing of fragrance or flavor composition comprising reaction of compound of formula II RC(O)OC(O)R 2 (II) wherein;
  • R is C 2 -C 12 alkyl, C 1 -C 12 alkyl carbonyl, C 2 -C 12 alkenyl, C2-C12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl optionally interrupted by at least one heteroatom;
  • R 2 is C 1 -C 6 alkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, aryl, heteroaryl, arylene, cycloalkyl optionally interrupted by at least one heteroatom; with a mixture of trans-3-hexen-l-ol present in an amount of from 55 % to 95 % by weight and cis-3-hexen-l-ol present in an amount of from 5 % to 45 % by weight, based on the weight of total mixture, optionally in the presence of a solvent.
  • a compound of formula (II) is selected from the group comprising: acetic anhydride, salicylic anhydride, propionic anhydride, cyclopropionic anhydride, tiglic anhydride, isobutyric anhydride, butyric anhydride, 2-methyl butyric anhydride, 2-methyl butanoic anhydride, 3 -methyl butanoic anhydride, benzoic anhydride, aminobenzoic anhydride, anthranilic anhydride, crotonic anhydride, phenyl acetic anhydride, 2-methyl-2-pentenoic anhydride, hexanoic anhydride, heptanoic anhydride, octanoic anhydride, nonanoic anhydride, decanoic anhydride, formic anhydride, isovaleric anhydride, lactic anhydride, levulinic anhydride, nicotinic anhydride, pyruvic anhydride,
  • the compound of formula (II) is acetic anhydride.
  • the molar ratio between the mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol and the compound of formula (II) is from about 2:1 to 1:20, preferably from about 1 : 1 to 1 : 15, more preferably from about 1 : 1 to 1 : 10, most preferably from about 1 : 1 to 1 : 1.5.
  • the reaction is performed in the presence of a solvent, wherein the solvent is selected from a group comprising water, toluene, dichloromethane, ethyl acetate, tetrahydrofuran, hexane, pentane, dimethylformamide, acetonitrile, dimethyl sulfoxide, diisopropyl ether, acetone, heptane, xylene, m-xylene, pyridine, diethyl ether, benzene, 1,4- dioxane, tert-butyl methyl ether, chloroform, 1,2-dichlorobenzene, octane, chlorobenzene, 1,2- dichloroethane, tert-butyl acetate, cyclohexane, cyclopentyl methyl ether, and the mixtures thereof.
  • the solvent is selected from a group comprising water, toluene, dichloromethane,
  • the solvent is toluene.
  • the solvent is cyclohexane.
  • the reaction is performed in the absence of a solvent.
  • the reaction of a mixture of trans-3-hexen-l-ol and cis-3- hexen-l-ol and a compound of formula (II) is performed in the temperature interval of from about 0°C to 130°C.
  • a preferred temperature interval is from about 50°C to 100°C, more preferably from about 75°C to 85°C.
  • the reaction is terminated when concentration of the mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol is between 0-50%, more preferably from 0-10%. In an embodiment, the reaction is terminated when no more than 1% of the starting mixture of trans-3-hexen-l-ol and cis-3-hexen-l-ol remains in the reaction media.
  • reaction mixture containing the ester products is worked up using common techniques including, but not limited to: addition of water and/or organic solvent, stirring, cooling, heating, phase separations, distillations, precipitations, recrystallizations, concentrations, filtrations, purifications, pH adjustments, extractions, and drying.
  • compositions according to any of the respective embodiments described herein comprise an ester of cis-3-hexen-l-ol and an ester of trans-3-hexen-l-ol.
  • Such odoriferous and/or flavourous compounds can be incorporated into the odor/flavor-imparting formulations and/or into articles-of-manufacturing wherein the presence of such odor/flavor- imparting compound is beneficial.
  • an odor-imparting formulation (a fragrance formulation) and/or flavor-imparting formulation (a flavor formulation) comprising the composition as described herein in any of the respective embodiments.
  • the odor-imparting formulation and/or flavor-imparting formulation comprises at least one additional odoriferous and/or flavourous substance.
  • the odor-imparting formulation and/or flavor-imparting formulation may optionally comprise at least one additional component which is not an odoriferous and/or flavourous substance, such as an acceptable carrier (e.g., alcoholic or water-containing carrier).
  • the acceptable carrier may optionally be cosmetically acceptable, agriculturally acceptable, edible, and/or suitable for a detergent.
  • fragrance and/or flavor composition as disclosed herein can be employed in widely varying amounts, depending upon the specific application and on the nature and quantity of other odorant ingredients and/or flavorant ingredients, if present.
  • the proportion of the fragrance and/or flavor composition is from 0.001 % to 20 % by weight, based on the total weight of the article-of-manufacturing or formulation containing same.
  • the proportion of the fragrance and/or flavor composition is from 20 % to 50 % by weight, based on the total weight of the article-of-manufacturing or formulation containing same.
  • odor-imparting and/or flavor-imparting composition may be provided as a fragrance and/or flavor concentrate which can be incorporated an article-of-manufacturing as described herein.
  • odor-imparting and/or flavor-imparting composition may be provided as a fragrance and/or flavor formulation which can be incorporated an article-of-manufacturing as described herein.
  • the present invention provides an article-of-manufacturing comprising a composition described herein.
  • the article of manufacturing includes detergents such as body care products, including bath/shower gels, hair conditioners, shampoos, liquid soaps, tablet soaps, cosmetic products and talcum powders; perfume products, particularly alcoholic perfumes; cleansing products or compositions such as fabric care products or ambient and home care such as fabric softeners; and in lifestyle products, such as pot pourri, reed diffusers, electric diffusers, candles and incense.
  • detergents such as body care products, including bath/shower gels, hair conditioners, shampoos, liquid soaps, tablet soaps, cosmetic products and talcum powders
  • perfume products particularly alcoholic perfumes
  • cleansing products or compositions such as fabric care products or ambient and home care such as fabric softeners
  • lifestyle products such as pot pourri, reed diffusers, electric diffusers, candles and incense.
  • Non-limiting examples of such article-of-manufacturing include; baby care, beauty care, fabric and home care, family care, feminine care, health care, snack and/or beverage products, and, more specifically, but without limitation, fine fragrance products or formulations (e.g. perfumes, colognes, eau de toilettes, after-shave lotions, pre-shave, face waters, tonics, and other fragrancecontaining compositions for application directly to the skin), diapers, bibs, wipes; products for and/or methods relating to treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling formulations or products; deodorants and antiperspirants, personal cleansing, cosmetics and skin care products or formulations, including creams, lotions, and other topically applied products, and shaving products; products for and/or methods relating to treating fabrics, hard surfaces and any other surfaces in the area of fabric and home care, including air care, car care, dishwashing, fabric conditioning (including softening), laundry detergent, laundry and rinse additive
  • cleaning composition includes washing agents, especially cleaning detergents, liquid, gel or paste-form all-purpose washing agents, liquid fine-fabric detergents, hand dishwashing agents or light duty dishwashing agents, machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types, cleaning and disinfecting agents, including antibacterial hand-wash types, cleaning bars, mouthwashes, denture cleaners, dentifrice, car or carpet shampoos, bathroom cleaners, hair shampoos and hair-rinses, shower gels and foam baths and metal cleaners, as well as cleaning auxiliaries such as bleach additives and “stain-stick” or pre-treat types, substrate-laden products such as dryer added sheets, dry and wetted wipes and pads, nonwoven substrates, and sponges, as well as sprays and mists.
  • cleaning and disinfecting agents including antibacterial hand-wash types, cleaning bars, mouthwashes, denture cleaners, dentifrice, car or carpet shampoos, bathroom cleaners, hair shampoos and hair-rinses, shower gels and foam
  • fabric care composition includes, unless otherwise indicated, fabric softening compositions, fabric enhancing compositions, fabric freshening compositions and combinations thereof.
  • the odor-imparting and/or flavor-imparting composition according to any of the embodiments described herein, or the formulation containing said composition may be directly mixed with the article-of-manufacturing to which it is applied.
  • the odor-imparting and/or flavor-imparting composition according to any of the embodiments described herein, or the formulation containing said composition may be entrapped or embedded in a delivery system such as, 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 the odoriferous substance(s) and/or flavourous substance(s) upon application of an external stimulus such as light, enzyme, or the like, and then applied to the article-of-manufacturing.
  • a delivery system such as, for example, polymers, capsules, microcapsules and nanocapsule
  • Embodiments of the present invention thus further encompass methods of manufacturing articles-of-manufacturing as described herein, which comprise incorporating an odoriferous and/or flavourous mixture of esters of trans-3-hexen-l-ol and esters of cis-3-hexen-l-ol or an odorimparting and/or an flavor- imparting formulation containing same in the article-of-manufacturing, typically using conventional techniques and methods.
  • the odor descriptors of the article-of-manufacturing may be improved, enhanced or modified.
  • the temperature was raised from 50 °C to 100 °C at a rate of 5 °C per minute, then from 100 °C to 220 °C at a rate of 10 °C per minute, followed by 3 minutes at 220 °C (total of 25 minutes).
  • Example 1 Preparation of trans-3 -hexen-l-yl acetate and cis-3-hexen-l-yl acetate mixture (by acetic acid):
  • trans-3-hexen-l-ol and cis-3-hexen-l-ol mixture were determined as less than 0.1 %, the reaction was cooled to room temperature and distilled under reduced pressure to obtain trans-3-hexen-l-ol acetate (69%) and cis-3-hexen-l-ol acetate (17%) mixture featuring purity of at least 86 % in at least 75 % yield, as determined by GC analysis.
  • trans-3-hexen-l-ol and cis-3-hexen-l-ol mixture were determined as less than 0.1 %, the mixture was cooled to 20 °C. Mixture was neutralized to pH 7.2 and phases were separated. Organic phase was distilled under reduced pressure to obtain trans-3-hexen-l-ol acetate (77.5%) and cis-3-hexen-l-ol acetate (19.8%) mixture featuring purity of at least 95 % in at least 82 % yield, as determined by GC analysis.
  • Example 4 Preparation of trans-3 -hexen-l-yl salicylate and cis-3-hexen-l-yl salicylate mixture (by salicylic acid):
  • aqueous phase was washed with toluene (10 mL), the organic phases were combined, toluene was evaporated, and the crude was distilled to obtain trans-3-hexen-l-yl salicylate (67.5%) and cis-3- hexen-l-yl salicylate (18.5%) mixture as a colorless oil featuring purity of at least 86 % at 60 % yield, as determined by GC analysis.
  • reaction was cooled to 80 °C and 50ml of cyclohexane were added. Temperature was raised to 125 °C and azeotrope distillation cyclohexane/methanol was proceeded until the presence of methyl salicylate was less than 0.5%.
  • the reaction mixture was distilled with PEG-2000 to obtain a mixture of trand-3 -hexenyl salicylate (78%) and cis-3-hexenyl salicylate (19.5%) as a colorless oil featuring purity of not less than 97% and yield of at least 60%. Odor of the final product was improved significantly after stirring for 84h at ambient conditions or introducing a deodorization process to the product mixture. Odor Characterization
  • Odor was analyzed by odor panels that consisted of individuals (panelists) selected and trained following the "Guidelines for Selection and Training of Sensory Panel Members" (ASTM Special Technical Publication 758). The Dravnieks descriptors was used as an acceptable guide to score the impotency level of each descriptor from 0 (not exist) to 5 (very noticeable and important in the overall odor profile)
  • FIGs. 1A-B is an odor spider chart, presenting the odor description of mixture of trans-3- hexen-l-yl acetate and cis-3-hexen-l-yl acetate alone (FIG. 1A) and in comparison, with cis-3- hexen-l-yl acetate (FIG. IB).
  • FIGs. 2A-B is an odor spider chart, presenting the odor description of mixture of trans-3- hexen-l-yl salicylate and cis-3-hexen-l-ol salicylate alone (FIG. 2A) and in comparison, with cis- 3-hexen-l-yl salicylate (FIG. 2B).
  • the inventive mixture of trans-3-hexen-l-yl acetate and cis-3-hexen-l-yl acetate features high score of green, floral, fruity and sweet odor descriptors, which are higher by 1 or 2 score than those of the cis-3 -hexen-l-yl acetate, indicating that it is a powerful odorant and may be used, inter alia, for providing mid- and top- notes in formulations and products containing same.
  • Odor descriptors such as fresh, green, herbal, aromatic, sweet, dew like, fruity, and floral, which are shared by the two substances, differ in score by more than 1.
  • trans-3-hexen-l-yl salicylate and cis-3-hexen-l -yl salicylate features floral, herbal, coconut- like odor with some dry and soapy odor descriptors.
  • odor descriptors such as floral, herbal, powdery, coconut- like, and powdery, which are shared by the trans-salicylate and czs-salicylate, differ in score by more than about 1 score.
  • Cz'.s-3-hcxcn-l -yl salicylate also, features a high odor score of mushroom and gasoline solvent - 4 and 3 score, while the mixture of lrans-3 -hexen-l-yl salicylate and cis- 3 -hexen-l-yl salicylate features nearly nullified mushroom and gasoline solvent odor descriptors (less than 1 score),
  • mixture of trans-3-hexen-l-yl salicylate and cis-3-hexen- 1 -yl salicylate feature a desirable soapy and coconut like odor descriptors (about 1 and 2 score, respectively) which are absent in cis-3-hexen-l-yl salicylate.

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Abstract

L'invention concerne une composition comprenant un mélange d'un ester trans-3-hexen-1-ol en une concentration s'inscrivant dans une plage de 55 % à 95 % en poids du mélange total et d'un ester cis.y-3-hexen-1-ol en une concentration s'inscrivant dans une plage de 5 % à 45 % en poids du mélange total, ses processus de préparation et ses utilisations.
PCT/IL2023/050391 2022-04-14 2023-04-13 Mélange d'isomères d'ester 3-hexényle et ses utilisations Ceased WO2023199324A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
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