EP1390335A1 - 2-methyl-4-ethyl-2-octene-1-aldehyde - Google Patents

2-methyl-4-ethyl-2-octene-1-aldehyde

Info

Publication number
EP1390335A1
EP1390335A1 EP02701297A EP02701297A EP1390335A1 EP 1390335 A1 EP1390335 A1 EP 1390335A1 EP 02701297 A EP02701297 A EP 02701297A EP 02701297 A EP02701297 A EP 02701297A EP 1390335 A1 EP1390335 A1 EP 1390335A1
Authority
EP
European Patent Office
Prior art keywords
methyl
aldehyde
ethyl
octene
oil
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02701297A
Other languages
German (de)
English (en)
Inventor
Thomas Markert
Ralph Nemitz
Marc Speitkamp
Theo Ten Pierik
Markus Schneider
Ralph Bunn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kao Corp
Original Assignee
Kao Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kao Corp filed Critical Kao Corp
Publication of EP1390335A1 publication Critical patent/EP1390335A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
    • C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation

Definitions

  • the present invention relates to 2-methyl-4-ethyl-2-octene-1-aldehyde, a process for its preparation and its use as a fragrance.
  • fragrance industry has a constant need for new fragrances with interesting fragrance notes.
  • the range of naturally available fragrances can be supplemented, on the other hand it is possible to make the necessary adjustments to changing fashionable tastes. It also makes it possible to meet the ever-increasing need for odor improvers for everyday products such as cosmetics and cleaning agents.
  • the compound of the general formula (I) fulfills the abovementioned requirements excellently in all respects and can advantageously be used as a fragrance with perfume-rich odor notes with good adhesive strength.
  • the present invention initially relates to 2-methyl-4-ethyl-2-octene-1-aldehyde of structure (I):
  • the invention relates to the use of 2-methyl-4-ethyl-2-octene-1-aldehyde (I) as a fragrance.
  • the compound (I) according to the invention is characterized by an odor characteristic in which iris and costus notes dominate. It has excellent stability in cosmetic and consumer perfume formulations.
  • the invention further relates to a process for the preparation of compound (I) by reacting 2-ethylhexanal with propionaldehyde in the presence of one or more nitrogen-containing organic compounds as catalysts in an organic solvent.
  • the catalysts used are preferably those nitrogen-containing organic compounds which contain at least one positively charged N atom per molecule, for example benzyltrimethylammonium hydroxide. Suitable catalysts are also nitrogen-containing bases such as 1,8-diazabicyclo [5.4.0] undec-7-ene and similar compounds known to those skilled in the art.
  • the reaction is preferably carried out in the absence of alkali metal hydroxides.
  • Organic solvent is also to be understood as meaning mixtures of organic solvents. Suitable solvents are, for example, toluene, xylenes, cyclohexane, methylcyclohexane and the like.
  • the reaction temperature is preferably set in the range from 20 to 200 ° C.
  • the range from 50 to 150 ° C. is particularly preferred.
  • the compound (I) ideally enhances the harmony and charisma as well as the naturalness and also the adhesion, the dosage being matched to the desired fragrance note, taking into account the other components of the composition.
  • the compound of formula (I) is particularly suitable for modifying and enhancing known compositions.
  • their extraordinary olfactory strength should be emphasized, which generally contributes to the refinement of the composition.
  • the compound of the formula (I) can be combined with numerous known fragrance ingredients, for example other fragrances of natural, synthetic or partially synthetic origin, essential oils and plant extracts.
  • the range of natural fragrances can include both volatile, medium and low volatile components.
  • the range of synthetic fragrances can include representatives from practically all classes of substances.
  • Natural products such as tree moss absolute, basil oil, agricultural oils such as bergotte oil, mandarin oil, etc., mastic absolute, myrtle oil, palmarosa oil, patchouli oil, petitgrain oil, wormwood oil, myrrh oil, olibanum oil, cedarwood oil, sandalwood oil, East Indian oil, guaiac oil Cabreuva,
  • alcohols such as farnesol, geraniol, citronellol, linalool, nerol, phenylethyl alcohol, rhodinol, cinnamon alcohol, sandalore [3-methyl-5- (2.2.3- trimethylcyclopent-3 -en- 1 -yl) pentan-2-ol], Sandela [3-isocamphyl- (5) - cyclohexanol], muguetanol,
  • aldehydes such as citral, helional ⁇ -, alpha-hexylcinnamaldehyde, hydroxycitronellal, lilial ⁇ - [p-tert-butyl- ⁇ -methyldihydrozimtaldehyde], methylnonylacetaldehyde,
  • ketones such as allylionone, ⁇ -ionone, ⁇ -ionone, isoraldein, methylionone, nootkatone, calone, ⁇ -, ß- and ⁇ -irone, Damascone,
  • esters such as allylphenoxyacetate, benzylsalicylate, cinnamylpropionate, citronellyl acetate, decyl acetate, dimethylbenzylcarbinyl acetate, ethyl acetoacetate, hexyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, vetivery acetate, cyclyl hexyl isyl nyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylylnyl isyl, nylyln
  • lactones such as gamma-undecalactone, l-oxaspiro [4.4] nonan-2-one, cyclopentadecanolide, ethylene brassylate, g) ethers such as herbavert, ambroxan, and various other components often used in perfumery such as musk and sandalwood Fragrance substances, indole, p-menthan-8-thiol-3-one, methyleugenol and methyl anthranilate.
  • lactones such as gamma-undecalactone, l-oxaspiro [4.4] nonan-2-one, cyclopentadecanolide, ethylene brassylate
  • ethers such as herbavert, ambroxan, and various other components often used in perfumery such as musk and sandalwood Fragrance substances, indole, p-menthan-8-thiol-3-one, methyleugenol and methyl anthranilate.
  • the usable proportions of the compound (I) according to the invention in fragrance compositions range from about 1-70% by weight, based on the mixture as a whole.
  • Compound (I) and compositions containing (I) can be used both for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants and in alcoholic perfumery (e.g. Eau de Cologne, Eau de Toilet, tincts) be det.
  • perfuming technical products such as detergents and cleaning agents, fabric softeners and textile treatment agents.
  • compositions are added to them in an olfactory effective amount, in particular in a concentration of 0.01-2% by weight, based on the entire product.
  • these values are not limiting limits, since the experienced perfumer can still achieve effects with even lower concentrations or build up novel complexes with even higher doses.
  • Example 1 shows the preparation of 2-methyl-4-ethyl-2-octen-1-al (I) in two different ways.
  • Example 1 demonstrates the process according to the invention, while Example 2 shows a process known from DE-A-26 13 996. It can be seen that the process according to Example 2 gives the compound (I) in considerably less yield than the process according to the invention according to Example 1.
  • Odor characteristic In the smell of Iris, Costus; after smell (after 24 hours on the smell strip) balsamic, myrrh resin, woman hair note.
  • Perfume rating The use of 2-methyl-4-ethyl-2-octen-l-al (I) brought about the natural aroma of a freshly cut, juicy and sour lemon in the composition.
  • a comparative composition that, like recipe B, was built, but did not contain the component (I) according to the invention, on the other hand, smelled into individual components, reminiscent of the bitter aroma of bitten lemon kernels, of fat, leather and walnut.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne du 2-méthyl-4-éthyl-2-octène-1-aldéhyde de structure (I), qui se caractérise par une odeur originale et intéressante à large diffusion et qui est adapté pour être utilisé comme matière odorante, par exemple dans des préparations cosmétiques, des produits techniques ou des produits de parfumerie à base d'alcool.
EP02701297A 2001-03-07 2002-02-26 2-methyl-4-ethyl-2-octene-1-aldehyde Withdrawn EP1390335A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10110857 2001-03-07
DE10110857A DE10110857A1 (de) 2001-03-07 2001-03-07 2-Methyl-4-ethyl-2-octen-1-aldehyd
PCT/EP2002/001990 WO2002070448A1 (fr) 2001-03-07 2002-02-26 2-methyl-4-ethyl-2-octene-1-aldehyde

Publications (1)

Publication Number Publication Date
EP1390335A1 true EP1390335A1 (fr) 2004-02-25

Family

ID=7676550

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02701297A Withdrawn EP1390335A1 (fr) 2001-03-07 2002-02-26 2-methyl-4-ethyl-2-octene-1-aldehyde

Country Status (5)

Country Link
US (1) US20040162447A1 (fr)
EP (1) EP1390335A1 (fr)
JP (1) JP4077726B2 (fr)
DE (1) DE10110857A1 (fr)
WO (1) WO2002070448A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040138510A1 (en) * 2003-01-13 2004-07-15 Kramarz Kurt W. Process for the co-production of alcohols
DE10361466A1 (de) * 2003-12-23 2005-07-28 Symrise Gmbh & Co. Kg Neutralisationsmittel für Gasodoriermittel

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH547250A (de) * 1970-03-24 1974-03-29 Givaudan & Cie Sa Verfahren zur herstellung von neuen (gamma),(delta)-ungesaettigten aldehyden.
DE2613996A1 (de) * 1975-04-04 1976-10-28 Grace W R & Co Aldehyde, deren entsprechende alkohole und ester dieser alkohole sowie verfahren zur herstellung dieser verbindungen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO02070448A1 *

Also Published As

Publication number Publication date
DE10110857A1 (de) 2002-09-12
JP4077726B2 (ja) 2008-04-23
WO2002070448A1 (fr) 2002-09-12
JP2004529109A (ja) 2004-09-24
US20040162447A1 (en) 2004-08-19

Similar Documents

Publication Publication Date Title
EP1280763B1 (fr) Composes trimethyldecene
EP0975570B1 (fr) Cetals de phenone et leur utilisation comme substances odoriferantes
EP1280790B1 (fr) Cetals cycliques et leur utilisation comme substances odoriferantes
EP1390335A1 (fr) 2-methyl-4-ethyl-2-octene-1-aldehyde
EP1284951B1 (fr) Derives de 3,3-dimethylcyclohexane
EP1296918B1 (fr) Dérivés de diméthylbenzène en tant qu'agents parfumants
EP1487816B1 (fr) Lactone ether
EP1373193A2 (fr) Derives de 2,3,5,5-tetramethyle hexanal
EP1476527B1 (fr) Utilisation de derives d'hexenal comme parfums
EP0863864B1 (fr) Composes carbonyle
DE10022971B4 (de) Verwendung von 4-(2,2,3-Trimethylcyclopentan-1-yl)-2-methylbutanal als Riechstoff
EP1485350B1 (fr) Utilisation de cetones insaturees en tant que substances odorantes
WO2001085663A1 (fr) Composes bicycloheptenyle
DE19521364A1 (de) Cyclohexyl-substituierte Alkanole
WO1995030406A1 (fr) Utilisation de 3-phenyl-4-pentenals et de leurs derives comme substances odorantes
WO1996025382A1 (fr) Produits de condensation
DE10143533A1 (de) Verwendung von Di-n-Hexylether als Riechstoff

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20030826

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE TR

17Q First examination report despatched

Effective date: 20040325

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20041005