EP1069176A1 - Aliphatische Estern und Ihre Verwendung als Duftstoff - Google Patents

Aliphatische Estern und Ihre Verwendung als Duftstoff Download PDF

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Publication number
EP1069176A1
EP1069176A1 EP00113222A EP00113222A EP1069176A1 EP 1069176 A1 EP1069176 A1 EP 1069176A1 EP 00113222 A EP00113222 A EP 00113222A EP 00113222 A EP00113222 A EP 00113222A EP 1069176 A1 EP1069176 A1 EP 1069176A1
Authority
EP
European Patent Office
Prior art keywords
compound
ethyl
formula
propanoate
dimethylpropoxy
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
EP00113222A
Other languages
English (en)
French (fr)
Other versions
EP1069176B1 (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
Original Assignee
Firmenich SA
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 Firmenich SA filed Critical Firmenich SA
Publication of EP1069176A1 publication Critical patent/EP1069176A1/de
Application granted granted Critical
Publication of EP1069176B1 publication Critical patent/EP1069176B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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 wavy line indicates that the asymmetric carbon located in position 2, can adopt an R or S type configuration, R 1 represents a methyl or ethyl radical and R 2 represents an ethyl radical, linear or branched propyl, or isobutyl, under as an optically active isomer or as a mixture of isomers.
  • esters of formula (I) have very useful odorous qualities and appreciated. They can therefore be used to prepare perfumes, perfume compositions and scented items. They are used to impart fragrant notes with character very natural fruity.
  • esters with a structure similar to the compounds (I) are known. We can quote for example Rev. Agroquim. Tecnol. Food. (1986), 26 (4), 597-601 which describes the use of ethyl 2-ethoxypropanoate as a racemic mixture for flavoring cheese, especially parmesan. Many others compounds having a structure close to that of the compounds which are the subject of the present invention have been described in the field of organic synthesis, but to our knowledge, in the prior art there is no reference or even suggestion of the possible usefulness of these esters as perfuming ingredients.
  • esters of formula (I) have completely surprising olfactory properties in view of the art that 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 varies from one compound to another.
  • the subnotes which which accompany it and which also vary from one compound to another allow outsourcing to basic compositions a whole range of olfactory nuances and thus make each compound capable of contributing to the variety of the perfumer's palette.
  • Ethyl (S) -2- (1,1-dimethylpropoxy) propanoate has a more spicy odor but which also includes a fragrant sub-note of chamomile type, this time accompanied by notes recalling 2-acetyl-4-methyl-4-pentanoate ethyl (EP B1 0178532; origin: Firmenich SA, Geneva, Switzerland), lees de wine, linalool or coriander.
  • the chamomile note of (S) -2-tert-butoxypropanoate propyl is accompanied by a licorice type sub-note with a very nice peach-apricot connotation.
  • Ethyl (S) -2-tert-butoxypropanoate has an odor which 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.
  • (S) -2- (1,1-dimethylpropoxy) propanoate propyl is a fragrance 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 recalls that of 8-p-menthen-2-ol acetate, with also a floral connotation, linalool, citrata mint. This floral, fruity note with sage connotation clary, citrata mint, has a fresh, very natural side, which is why it is particularly appreciated by perfumers.
  • the compounds of the invention are equally suitable for use in fine perfumery, in perfumes, eau de toilette or aftershave lotions, than others common jobs in perfumery such as perfuming soaps, shower gels or bath, hygiene products, or hair treatment products like 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 as liquid or solid detergents intended for the treatment of textiles, fabric softeners or in detergent compositions or cleaning products intended for cleaning of dishes or various surfaces, for domestic or industrial use.
  • the compounds of the invention can be used alone or in mixture with other perfuming ingredients, solvents or adjuvants of use 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
  • fragrance ingredients belong to chemical classes too as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, hydrocarbons terpenic, heterocyclic nitrogen or sulfur compounds, as well as essential oils of natural or synthetic origin. Many of these ingredients are also listed in reference texts such as the book by S. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or more recent versions, or in other works of a similar nature.
  • the proportions in which the compounds according to the invention can be incorporated in the aforementioned miscellaneous products vary in a range of values extent. These values depend on the nature of the article or product you want to scent and the desired olfactory effect, as well as the nature of the co-ingredients in a composition given when the compounds of the invention are used in mixture with perfume co-ingredients, solvents or adjuvants commonly used in the art.
  • the first step is that described under a) .
  • the second was carried out according to an operating protocol 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 choosing the suitable 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 protocol 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 carried out according to a protocol similar to that described under b) , using a suitable reagent as indicated in diagram 1.
  • a basic composition for male eau de toilette 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 Essen Juniper synth 40 English clove essence 10 Lavender essence 120 Linalol 170 Lyral ® 60 Mandarin essence 30 Crystal foam 50 10% rose oxide 20 Siberian pine essence 20 Essence of patchouli 150 Polysantol ® 30 Amyl salicylate 20 Benzyl salicylate 440 Ylang extra 30 Zestover at 10% 70 Total 1800
  • a basic composition intended 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 10% 10 Iso E super 10 Iralia ® 10 Gros Lavandin 50 Lyral ® 15 10% crystal foam 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)
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 true EP1069176A1 (de) 2001-01-17
EP1069176B1 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
WO2015003985A1 (en) 2013-07-08 2015-01-15 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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0659856A1 (de) * 1993-12-24 1995-06-28 Nissan Chemical Industries, Limited Polyimidlackierung

Family Cites Families (3)

* 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
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP0659856A1 (de) * 1993-12-24 1995-06-28 Nissan Chemical Industries, Limited Polyimidlackierung

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
CAINELLI G ET AL: "Diastereofacial Selectivity in the Reaction of Chiral N-Trimethylsilyl Imines with Ester Enolates: Preparation of trans -Azetidin-2-ones in High Stereocontrolled Fashion", TETRAHEDRON,NL,ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, vol. 52, no. 5, 29 January 1996 (1996-01-29), pages 1685 - 1698, XP004104473, ISSN: 0040-4020 *
PATENT ABSTRACTS OF JAPAN vol. 018, no. 017 (E - 1488) 12 January 1994 (1994-01-12) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015003985A1 (en) 2013-07-08 2015-01-15 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
DE60013513T2 (de) 2005-09-15
JP4008645B2 (ja) 2007-11-14
EP1069176B1 (de) 2004-09-08
US6509312B1 (en) 2003-01-21

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