EP1069176B1 - Aliphatische Ester und Ihre Verwendung als Duftstoff - Google Patents

Aliphatische Ester und Ihre Verwendung als Duftstoff Download PDF

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Publication number
EP1069176B1
EP1069176B1 EP00113222A EP00113222A EP1069176B1 EP 1069176 B1 EP1069176 B1 EP 1069176B1 EP 00113222 A EP00113222 A EP 00113222A EP 00113222 A EP00113222 A EP 00113222A EP 1069176 B1 EP1069176 B1 EP 1069176B1
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EP
European Patent Office
Prior art keywords
compound
ethyl
formula
perfume
cdcl
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.)
Expired - Lifetime
Application number
EP00113222A
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English (en)
French (fr)
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EP1069176A1 (de
Inventor
Wolfgang Klaus Giersch
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.)
Firmenich SA
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Firmenich SA
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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
    • C11B9/0019—Aliphatic compounds containing oxygen as the only heteroatom carbocylic acids; Salts or esters thereof

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to a compound of formula in which the corrugated line indicates that the asymmetric carbon located in position 2, can adopt a configuration of R or S type, R 1 represents a methyl or ethyl radical and R 2 represents an ethyl radical, linear or branched propyl, or isobutyl, under form of an optically active isomer or as a mixture of isomers.
  • esters of formula (I) have very useful odorous qualities and appreciated. They can thus be used to prepare perfumes, perfume compositions and scented articles. They are used to impart fragrant notes of character fruity very natural.
  • esters of structure similar to the compounds (I) are known. We can cite for example Rev. Agroquim. Tecnol. Food. (1986), 26 (4), 597-601 which discloses the use of ethyl 2-ethoxypropanoate as a racemic mixture for the flavoring of cheese, especially parmesan cheese. Many others compounds having a structure close to that of the compounds which are the subject of this invention were described in the field of organic synthesis but to our knowledge, there exists in the prior art no reference or even suggestion of the possible usefulness of these esters as perfuming ingredients.
  • esters of formula (I) have olfactory properties quite surprising in view of the art and make their use in perfumery very interesting.
  • the compounds of formula (I) are characterized by an odor whose note of Fruity type head, very natural, makes them particularly appreciated by perfumers.
  • the intensity of this note declines from one compound to another.
  • the sub-notes that accompany it and which also vary from one compound to another allow to impart base compositions a whole range of olfactory nuances and thus make each composed to contribute to the variety of the perfumer's palette.
  • a chamomile-type connotation This one is particularly distinct in the odor of ethyl (R) -2- (1,1-dimethylpropoxy) propanoate whose fruity is also very strong.
  • Ethyl (S) -2- (1,1-dimethylpropoxy) propanoate has a more spicy smell but also includes a fragrant subnote of chamomile type, this time with notes pronounced of 2-acetyl-4-methyl-4-pentanoate (EP B1 0178532, origin: Firmenich SA, Geneva, Switzerland), the dregs of wine, linalool or coriander.
  • the chamomile note of (S) -2-tert-butoxypropanoate of propyl is she accompanied by a liquorice sub-note with a very pretty peach-apricot connotation.
  • (S) -2-tert-butoxypropanoate ethyl has a scent the fruity character is also velvety, ethereal, sweet, but it also has notes reminiscent of mint. Its fresh smell keeps the natural side common to all compounds of the invention.
  • Propyl is a fragrant ingredient of choice. It has an odor whose top note fruity is accompanied by smoky and refreshing notes. The smell keeps its side natural. In the background, it is pronounced of 8-p-menthen-2-ol acetate, floral connotation, linalool, mint citrata. This floral, fruity note with sage connotation sclarée, mint citrata, has a fresh side, very natural, which is worth to be particularly appreciated by perfumers.
  • the compounds of the invention are equally suitable for use in perfumery, in perfumes, eau de toilette or after-shave lotions, than at other current perfumery jobs such as the perfuming of soaps, shower gels or bath, hygiene products, or products for the treatment of hair such as shampoos or after shampoos or other hair care products, as well as body deodorants and ambient deodorants, or cosmetic preparations.
  • Esters (I) can also be used in applications such as liquid or solid detergents for the treatment of textiles, textile softeners or in detergent compositions or cleaning products intended for cleaning of dishes or various surfaces, for domestic or industrial purposes.
  • the compounds of the invention can be used alone or mixed with other perfuming ingredients, solvents or adjuvants current in perfumery.
  • perfuming ingredients such as sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate
  • fragrance ingredients belong to chemical classes too various alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, hydrocarbons terpene, nitrogenous or sulfur-containing heterocyclic compounds and essential oils of natural or synthetic origin. Many of these ingredients are also listed in reference texts such as S. Arctander's book, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature.
  • the first step is that described under a) .
  • the second was carried out according to an operating procedure similar to that described under b) , by choosing the alcohol used as reagent according to the desired final product (see diagram 1).
  • the compound was prepared in one step according to a procedure similar to that described under a) by selecting the appropriate reagent as described in Scheme 1 (step a).
  • the first step is that described under e) .
  • the second was carried out according to an operating procedure similar to that described under b) , by choosing the alcohol used as reagent according to the desired final product (see diagram 1).
  • This compound was synthesized in two stages.
  • the first step is that described under h) .
  • the second step is performed according to a protocol similar to that described under b) , using a suitable reagent as shown in diagram 1.
  • a basic composition for male toilet water was prepared from the following ingredients: ingredients Parts by weight Benzyl acetate 40 Geranyl acetate 10 Linalyl acetate 100 cedarleaf 20 Allyl amyl glycolate 10 Ambrox ® 20 Essence of aspic 100 Bergamot essence 180 citral 30 coumarin 20 Tarragon essence 10 Juniper ess. synth 40 English clove oil 10 Essence of lavandin 120 linalool 170 Lyral ® 60 Mandarin essence 30 Crystal foam 50 10% Rose Oxide 20 Siberian pine species 20 Essence of patchouli 150 Polysantol ® 30 Amyl salicylate 20 Benzyl salicylate 440 Ylang extra 30 Zestover at 10% 70 Total 1800
  • a base composition for a body deodorant was prepared from the following ingredients: ingredients Parts by weight Allyl amyl glycolate 20 Ambrox ® at 10% 15 Bergamot synth. 180 Civet synth. at 1% 30 ⁇ -Damascone at 10% 50 Lorysia ® 10 Galaxolide ® 50 MIP 45 Galbex ® 30 Essence of Chinese geranium 15 Hedione ® 60 Indolene at 10% 10 Iso E super 10 Iralia ® 10 Lavandin grosso 50 Lyral ® 15 Crystal foam 10% 50 Tonalide ® 40 Vertofix heart 110 Total 750

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)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)

Claims (5)

  1. Verwendung einer Verbindung der Formel
    Figure 00130001
    worin die Wellenlinie angibt, daß der asymmetrische Kohlenstoff in Position 2 eine Konfiguration vom R- oder S-Typ annehmen kann, R1 einen Methyl- oder Ethylrest darstellt und R2 einen Ethylrest, einen linearen oder verzweigten Propylrest oder einen Isobutylrest darstellt, in Form eines optisch aktiven Isomers oder in Form einer Isomerenmischung, als Duftbestandteil zur Herstellung, von Duftzusammensetzungen oder parfümierten Artikeln.
  2. Duftzusammensetzung oder parfümierter Artikel, enthaltend als Wirkstoff eine Verbindung der Formel (I), wie sie in Anspruch 1 definiert ist.
  3. Parfümierter Artikel nach Anspruch 2 in Form eines Parfums oder eines Eau de Toilette, einer After-Shave-Lotion, eines Kosmetikpräparats, einer Seife, eines Shampoos oder After-Shampoos oder eines anderen Haarpflegeprodukts, eines Bade- oder Duschgels, eines Körperdeodorants oder eines Raumlufterfrischers, eines Waschmittels oder eines Gewebeweichspülers oder eines Pflegemittels.
  4. Verbindung der Formel (I) wie in Anspruch 1 definiert, ausgenommen der (S)-2-tert-Butoxypropansäureethylester.
  5. Verbindung nach Anspruch 4, nämlich (S)-2-(1,1-Dimethylpropoxy)propansäurepropylester.
EP00113222A 1999-07-14 2000-06-21 Aliphatische Ester und Ihre Verwendung als Duftstoff Expired - Lifetime EP1069176B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH130399 1999-07-14
CH130399 1999-07-14

Publications (2)

Publication Number Publication Date
EP1069176A1 EP1069176A1 (de) 2001-01-17
EP1069176B1 true EP1069176B1 (de) 2004-09-08

Family

ID=4207286

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00113222A Expired - Lifetime EP1069176B1 (de) 1999-07-14 2000-06-21 Aliphatische Ester und Ihre Verwendung als Duftstoff

Country Status (6)

Country Link
US (1) US6509312B1 (de)
EP (1) EP1069176B1 (de)
JP (1) JP4008645B2 (de)
AT (1) ATE275617T1 (de)
DE (1) DE60013513T2 (de)
ES (1) ES2228355T3 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10047319B2 (en) 2013-07-08 2018-08-14 Firmenich Sa 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MX2010013255A (es) 2008-06-04 2010-12-21 Firmenich & Cie Aromatizante floral.
US7973194B1 (en) 2010-03-18 2011-07-05 Eastman Chemical Company High solvating cyclohexane dicarboxylate diesters plasticizers
EP3816269A4 (de) * 2018-06-26 2021-08-11 Mitsubishi Gas Chemical Company, Inc. Duftstoffzusammensetzung mit ss-methoxyisobuttersäure-esterverbindung und verwendung als duftstoff
WO2024223790A1 (en) * 2023-04-28 2024-10-31 Basf Se Use of alkyl 4-alkoxypentanoates as aroma chemicals

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0178532B1 (de) 1984-10-18 1990-06-06 Firmenich Sa Ethyl-2-acetyl-4-methyl-4-pentenoat enthaltende Duftzusammensetzungen und parfümierte Waren
JPH05258611A (ja) * 1992-03-09 1993-10-08 Toutoku Toryo Kk 絶縁電線用塗料および絶縁電線
TW305869B (de) 1993-12-24 1997-05-21 Nissan Chemical Ind Ltd
ES2232910T3 (es) * 1997-12-08 2005-06-01 Firmenich Sa Utilizacion del 3-metil-2-oxopentanoato de etilo como ingrediente perfumante.
US6159929A (en) * 1997-12-08 2000-12-12 Firmenich Sa Optically active esters and their use as perfuming ingredients

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10047319B2 (en) 2013-07-08 2018-08-14 Firmenich Sa 1-isopropoxy-1-oxopropan-2-yl pivalate as perfuming ingredient

Also Published As

Publication number Publication date
ES2228355T3 (es) 2005-04-16
DE60013513D1 (de) 2004-10-14
ATE275617T1 (de) 2004-09-15
JP2001055599A (ja) 2001-02-27
EP1069176A1 (de) 2001-01-17
DE60013513T2 (de) 2005-09-15
JP4008645B2 (ja) 2007-11-14
US6509312B1 (en) 2003-01-21

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