EP1485350A1 - Utilisation de cetones insaturees en tant que substances odorantes - Google Patents

Utilisation de cetones insaturees en tant que substances odorantes

Info

Publication number
EP1485350A1
EP1485350A1 EP03744331A EP03744331A EP1485350A1 EP 1485350 A1 EP1485350 A1 EP 1485350A1 EP 03744331 A EP03744331 A EP 03744331A EP 03744331 A EP03744331 A EP 03744331A EP 1485350 A1 EP1485350 A1 EP 1485350A1
Authority
EP
European Patent Office
Prior art keywords
compounds
unsaturated
methyl
ppm
cyclic
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.)
Granted
Application number
EP03744331A
Other languages
German (de)
English (en)
Other versions
EP1485350B1 (fr
Inventor
Thomas Markert
Volker Porrmann
Frank Rittler
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 EP1485350A1 publication Critical patent/EP1485350A1/fr
Application granted granted Critical
Publication of EP1485350B1 publication Critical patent/EP1485350B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • C11B9/0026—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

Definitions

  • the present invention relates to the use of unsaturated ketones of special structure as fragrances.
  • 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 present invention firstly relates to the use of unsaturated ketones of the general structure (I)
  • radicals R h R 2 , R 3 , R and R 5 independently of one another denote hydrogen or alkyl groups having 1 to 6 carbon atoms, which may be saturated or unsaturated, straight-chain or branched or cyclic, as odoriferous substances.
  • the invention relates to fragrance concentrates consisting of one or more of the compounds of the general structure (I) specified above.
  • the compounds (I) according to the invention are distinguished by an odor characteristic in which fruity-herbaceous notes dominate. They have excellent stability in cosmetic and consumer perfume formulas.
  • the compounds (I) can be prepared per se by known synthetic methods of organic chemistry. Particularly suitable options for the preparation of the compounds (I) can be found in the example section.
  • Another object of the invention is a process for the preparation of compounds of the above general formula (I):
  • the OH group of the alkanols is preferably primary, but can also be secondary or tertiary.
  • the compounds (I) enhance 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 constituents of the composition.
  • the compounds 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,
  • aldehydes such as citral, HelionaP% alpha-hexylcinnamaldehyde, hydroxycitronellal
  • ketones such as allylionone, ⁇ -ionone, ⁇ -ionone, isoraldein, methylionone, nootkatone, calone, ⁇ -, ß- and ⁇ -irone, Damascone,
  • esters such as allylphenoxyacetate, benzyl salicylate, cinnamyl propionate, citronellyl acetate, decyl acetate, dimethylbenzylcarbinylacetate, ethyl acetoacetate, witch- nyl isobutyrate, linalyl acetate, methyl dihydrojasmonate, vetiveryl acetate, cyclohexyl salicylate, isobornyl isobutyrate, evernyl, (f) lactones such as gamma-undecalactone, l-oxaspiro [4.4] nonan-2-one, cyclopentadex-xanolidone, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bromide, ethylene bro
  • the usable proportions of the compounds (I) according to the invention or their mixtures in fragrance compositions range from about 1-70% by weight, based on the mixture as a whole.
  • Mixtures of the compounds (I) according to the invention and compositions of this type can be used for perfuming cosmetic preparations such as lotions, creams, shampoos, soaps, ointments, powders, aerosols, toothpastes, mouthwashes, deodorants as well as in alcoholic perfumery (e.g. Eau de Cologne, Eau de toilet, tincts) can be used.
  • 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 achieve effects with even lower concentrations or build up new types of complexes with even higher doses. Examples
  • the 4 olefinic protons gave the following signals: 2 doublets (2H, terminal proto- side chain) at 5.0 ppm, the olefinic proton in the cyclohexane ring gave a weakly split signal at 5/35 ppm and the single olefinic proton in the side chain gave 2 strongly split signals (quintets, 1 H) at 5.65 ppm, superimposed.
  • smell In the smell Davana, fruity, green, muguet and in the smell, after 24 hours on the smell strip, weak rhubarb.
  • Apparatus 0.5 L agitator with thermometer, reflux condenser and water separator
  • the proton adjacent to the keto group on the cyclohexene ring appeared as a strongly split multiplet at 2.2 ppm.
  • the olefinic protons gave a ddd at 5.9 ppm (IH), a doublet from the doublet at 5.0 ppm (2Hs) and a broad signal for the olefinic proton in the cyclohexene ring at 5.4 ppm).
  • Odor characteristics Green, fruity, greasy, lime in the smell and after smell, fruity, woody, muguet, bergamot after 24 hours on the smell strip.
  • Apparatus 0.5 L agitator with thermometer, reflux condenser and water separator.
  • the methyl group at the end of the side chains gave a signal mountain from superimposed triplets at 0.9 ppm (3Hs). Two multiplets (approx. 4 Hs) were between 1.1 and 1.4 ppm; these are probably assigned to the 2 CH 2 groups from the side chain.
  • the methyl group a cyclohexene ring gave broad singlets at 1.6 and 1.7 ppm (approx. 1.5 Hs each).
  • At 2.1 and 2.15 ppm there were 2 singlets with one echo each (approx.
  • Odor characteristics Green, herbaceous, fresh, citrus, jasmine note in the smell and after smell, after 24 hours on the smell strip: terpene, grapefruit, skin.

Landscapes

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

Abstract

Cétones insaturées de structure générale (I) dans laquelle les restes R1, R2, R3, R4 et R5 représentent indépendamment les uns des autres hydrogène ou des groupes alkyle ayant 1 à 6 atomes de carbone qui peuvent être saturés ou insaturés, linéaires ou ramifiés ou cycliques. Lesdites cétones présentent des propriétés odoriférantes intéressantes et originales à forte diffusion et sont adaptées en tant que substances odorantes, par exemple dans des préparations cosmétiques, des produits techniques ou la parfumerie à base d'alcool.
EP03744331.4A 2002-03-19 2003-02-17 Utilisation de cetones insaturees en tant que substances odorantes Expired - Lifetime EP1485350B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10212026A DE10212026A1 (de) 2002-03-19 2002-03-19 Verwendung von ungesättigten Ketone als Riechstoffe
DE10212026 2002-03-19
PCT/EP2003/001561 WO2003078391A1 (fr) 2002-03-19 2003-02-17 Utilisation de cetones insaturees en tant que substances odorantes

Publications (2)

Publication Number Publication Date
EP1485350A1 true EP1485350A1 (fr) 2004-12-15
EP1485350B1 EP1485350B1 (fr) 2013-07-17

Family

ID=27797897

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03744331.4A Expired - Lifetime EP1485350B1 (fr) 2002-03-19 2003-02-17 Utilisation de cetones insaturees en tant que substances odorantes

Country Status (6)

Country Link
US (2) US20050119158A1 (fr)
EP (1) EP1485350B1 (fr)
JP (1) JP4346448B2 (fr)
DE (1) DE10212026A1 (fr)
ES (1) ES2426001T3 (fr)
WO (1) WO2003078391A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3532018B1 (fr) * 2016-10-28 2024-07-17 Basf Se Utilisation du 1-[(4r)-4-methylcyclohexen-1-yl]ethanone en tant que compose aromatique

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH586551A5 (fr) * 1974-01-29 1977-04-15 Firmenich & Cie
CH645337A5 (fr) * 1980-08-22 1984-09-28 Firmenich & Cie Composes cycloaliphatiques insatures, procede pour leur preparation et composition parfumante les contenant.
US4507225A (en) 1983-04-21 1985-03-26 International Flavors & Fragrances Inc. Process for augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles with 1-phenylpenten-4-one-1 and methyl homologues thereof
US4548743A (en) * 1984-04-20 1985-10-22 International Flavors & Fragrances Inc. Ketal and use in perfumery
JPH0570449A (ja) 1991-09-12 1993-03-23 Sumitomo Chem Co Ltd 青カメムシ類の性フエロモンの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO03078391A1 *

Also Published As

Publication number Publication date
WO2003078391A1 (fr) 2003-09-25
DE10212026A1 (de) 2003-10-02
US7582600B2 (en) 2009-09-01
US20090054299A1 (en) 2009-02-26
JP2005520875A (ja) 2005-07-14
JP4346448B2 (ja) 2009-10-21
US20050119158A1 (en) 2005-06-02
EP1485350B1 (fr) 2013-07-17
ES2426001T3 (es) 2013-10-18

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