EP0085352A2 - Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum - Google Patents

Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum Download PDF

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Publication number
EP0085352A2
EP0085352A2 EP83100415A EP83100415A EP0085352A2 EP 0085352 A2 EP0085352 A2 EP 0085352A2 EP 83100415 A EP83100415 A EP 83100415A EP 83100415 A EP83100415 A EP 83100415A EP 0085352 A2 EP0085352 A2 EP 0085352A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
oxime
compounds
hydrocarbon radical
nonen
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
EP83100415A
Other languages
German (de)
English (en)
Other versions
EP0085352B1 (fr
EP0085352A3 (en
Inventor
Paul Albert Dr. Ochsner
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.)
Givaudan SA
Original Assignee
L Givaudan and Co 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 L Givaudan and Co SA filed Critical L Givaudan and Co SA
Publication of EP0085352A2 publication Critical patent/EP0085352A2/fr
Publication of EP0085352A3 publication Critical patent/EP0085352A3/de
Application granted granted Critical
Publication of EP0085352B1 publication Critical patent/EP0085352B1/fr
Expired 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

Definitions

  • the invention relates to new fragrances. These are the compounds of the formula wherein R is an olefinically monounsaturated hydrocarbon radical, the unsaturation being in the ⁇ , ⁇ position, and R 'is a saturated hydrocarbon radical having 1 to 4 carbon atoms, and the number of carbon atoms in R + R' is 10-13.
  • Formula I is intended to encompass the syn and anti forms of oxime I.
  • the anti form is preferred.
  • radicals R and R ' can be straight-chain or branched.
  • R and R ' preferably contain 10 to 12, particularly preferably 10 or 11 carbon atoms.
  • the invention further relates to a process for the preparation of the compounds I.
  • This method is characterized in that a compound of the formula wherein R and R 'have the above meanings, reacted with hydroxylamine or one of its salts.
  • the reaction of the compound of formula II with hydroxylamine or a salt thereof can be carried out according to methods known per se, see, for example, organic medicine, basic organic chemical internship, collective of authors; 7th edition; VEB German Publishing House of Sciences; Berlin 1967, 375:
  • the hydroxylamine is expediently left as a salt, for example as hydrochloride or sulfate in an alkaline solution containing pyridine or in an aqueous alkaline solution with the K etonII react; the reaction temperature is preferably the reflux temperature of the reaction mixture.
  • the oximes can be purified by distillation.
  • the starting ketones II are known or can be prepared by methods known per se, e.g. by chain extension of simple, commercially available ketones, for example using allyl halides.
  • the compounds I have special organoleptic properties which make them particularly suitable as fragrances.
  • the invention accordingly also relates to the use of the compounds I as fragrances.
  • the oximes according to the invention are distinguished by a special combination of perfume properties. They are all either colorless or at most weakly colored, easily accessible, the individual approaches are constant in smell, not irritating, stable and easy to use.
  • the compounds of the formula I are generally pronounced of notes of black currant, sage, ivy, grapefruit; Due to their natural smell and their retention time (long-term effect, especially regarding freshness) they are particularly suitable for the modification of known, e.g.
  • Smell black currant, natural, earthy, herbaceous.
  • Smell black currant, sage, lavender, grapefruit, leek.
  • Smell of fresh vegetables, of peas, daisies, dogwood shrubs, well adhering.
  • Smell of fresh vegetables, of ivy, dogwood shrub.
  • Smell of fresh vegetables, of tomato leaves, of black currants, very natural looking.
  • Smell of grapefruit, currants, well adhering.
  • Smell like yolk flowers, very natural.
  • the compounds of the formula I can be used within wide limits, which can range, for example, from 0.1 (detergents) to 50% (alcoholic solutions) in compositions, without these values being intended to represent limit values, however, since the experienced perfumer can use even lower ones Concentrations can achieve effects or can build up new types of complexes with even higher doses.
  • the preferred concentrations are between 0.5 and 25%.
  • the compositions produced with I can be used for all types of perfumed consumer goods (Eaux de Cologne, Eaux de Toilette, extras, lotions, creams, shampoos, soaps, ointments, powders, deodorants, detergents, tobacco, etc.).
  • the compounds I can be used in the production of compositions and - as the composition above shows - using a wide range of known odoriferous substances.
  • the known fragrances listed above can be used in a manner known to the perfumer, e.g. from W.A. Poucher, Perfumes, Cosmetics and Soaps 2, 7th edition, Chapman and Hall, London 1974.
  • Perfumery base generally floral

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Tea And Coffee (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Detergent Compositions (AREA)
EP83100415A 1982-02-03 1983-01-19 Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum Expired EP0085352B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH645/82 1982-02-03
CH64582 1982-02-03

Publications (3)

Publication Number Publication Date
EP0085352A2 true EP0085352A2 (fr) 1983-08-10
EP0085352A3 EP0085352A3 (en) 1983-10-19
EP0085352B1 EP0085352B1 (fr) 1986-01-22

Family

ID=4191831

Family Applications (1)

Application Number Title Priority Date Filing Date
EP83100415A Expired EP0085352B1 (fr) 1982-02-03 1983-01-19 Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum

Country Status (4)

Country Link
US (1) US4544714A (fr)
EP (1) EP0085352B1 (fr)
JP (1) JPS58134071A (fr)
DE (1) DE3361874D1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0191365A1 (fr) * 1985-02-06 1986-08-20 L. GIVAUDAN & CIE Société Anonyme Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés
EP0672746A1 (fr) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Ethers d'oximes et compositions parfumantes et aromatisantes les contenant
WO2005110961A1 (fr) * 2004-05-13 2005-11-24 Firmenich Sa Cetones non cycliques entraves en tant qu'ingredient de parfumerie
WO2019076926A1 (fr) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Substances odorantes et compositions comprenant des substances odorantes

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4678604A (en) * 1985-09-13 1987-07-07 Givaudan Corporation 2-(1'-hydroxyimino-ethyl)-1,3,3,4,4-pentamethylcyclopentene and fragrance compositions containing same
US5066641A (en) * 1990-09-27 1991-11-19 International Flavors & Fragrances Inc. 3,5,5-trimethylhexanal oxime and organoleptic uses thereof
DE19539625A1 (de) * 1995-10-16 1997-04-17 Haarmann & Reimer Gmbh Verfahren zur Herstellung von 2,4,4,7-Tetramethyl-oct-6-en-3-on und dessen Verwendung als Riechstoff
US6872697B2 (en) * 2001-09-07 2005-03-29 Firmenich Sa Oxime as perfuming ingredient
US7494968B2 (en) 2004-05-13 2009-02-24 Firmenich Sa Non-cyclic hindered ketones as perfuming ingredient
EP2552245B1 (fr) * 2010-03-26 2018-11-14 Philip Morris Products S.A. Inhibition de l'irritation sensorielle pendant la consommation de produits de tabac non fumables

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1305994A (fr) * 1961-07-21 1962-10-13 Rhone Poulenc Sa Nouveaux dérivés terpéniques et leur préparation
US3453317A (en) * 1962-07-11 1969-07-01 Hoffmann La Roche Unsaturated carbonyl compounds and processes
US3637533A (en) * 1967-02-14 1972-01-25 Givaudan Corp Perfume-containing compositions containing certain oximes as olfactory agents
CH597125A5 (fr) * 1973-07-05 1978-03-31 Hoffmann La Roche
US4052194A (en) * 1974-01-24 1977-10-04 Merrill Wilcox Oxime abscission agents
EP0045861B1 (fr) * 1980-08-08 1984-10-03 L. GIVAUDAN & CIE Société Anonyme Composés insaturés, leur procédé de préparation, leur utilisation comme parfums ainsi que les compositions parfumantes les contenant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0191365A1 (fr) * 1985-02-06 1986-08-20 L. GIVAUDAN & CIE Société Anonyme Oximes araliphatiques, procédé pour leur préparation et compositions odoriférantes contenant de tels composés
EP0672746A1 (fr) * 1994-03-18 1995-09-20 Givaudan-Roure (International) S.A. Ethers d'oximes et compositions parfumantes et aromatisantes les contenant
WO2005110961A1 (fr) * 2004-05-13 2005-11-24 Firmenich Sa Cetones non cycliques entraves en tant qu'ingredient de parfumerie
WO2019076926A1 (fr) * 2017-10-17 2019-04-25 S H Kelkar & Company Limited Substances odorantes et compositions comprenant des substances odorantes
US11549079B2 (en) 2017-10-17 2023-01-10 S H Kelkar & Company Limited Odorants and compositions comprising odorants

Also Published As

Publication number Publication date
US4544714A (en) 1985-10-01
EP0085352B1 (fr) 1986-01-22
JPS58134071A (ja) 1983-08-10
DE3361874D1 (en) 1986-03-06
JPH0361661B2 (fr) 1991-09-20
EP0085352A3 (en) 1983-10-19

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