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EP0214588B1 - Oxime cyclique - Google Patents

Oxime cyclique Download PDF

Info

Publication number
EP0214588B1
EP0214588B1 EP86112050A EP86112050A EP0214588B1 EP 0214588 B1 EP0214588 B1 EP 0214588B1 EP 86112050 A EP86112050 A EP 86112050A EP 86112050 A EP86112050 A EP 86112050A EP 0214588 B1 EP0214588 B1 EP 0214588B1
Authority
EP
European Patent Office
Prior art keywords
oxime
oil
givaudan
mixture
linalyl
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
EP86112050A
Other languages
German (de)
English (en)
Other versions
EP0214588A2 (fr
EP0214588A3 (en
Inventor
Roman Kaiser
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 EP0214588A2 publication Critical patent/EP0214588A2/fr
Publication of EP0214588A3 publication Critical patent/EP0214588A3/de
Application granted granted Critical
Publication of EP0214588B1 publication Critical patent/EP0214588B1/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
    • C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms

Definitions

  • the invention relates to a new fragrance. It is the 2- (1'-hydroximino-ethyl) -1,3,3,4,4-pentamethylcyclopentene, that is to say the compound of the formula
  • Formula 1 is intended to loosen both geometrical forms, ie the syn and anti forms of oxime I.
  • I can be obtained by using 2 acetyl-1,3,3,4,4-pentamethylcyclopentene, ie the ketone of the formula reacted with hydroxylamine or one of its salts. (Bull. Soc. Chim. De France, No. 5, 1961).
  • a II-rich product can now easily be obtained by treating the product mixture mentioned with a base, such as aqueous sodium hydroxide solution, and working up the acidified reaction mixture.
  • a base such as aqueous sodium hydroxide solution
  • the product remaining after distilling off the more volatile compounds now contains, for example, 67% II in addition to the acyclic ketones Ilb (approx. 15%), IIc (approx. 7%) and Ild (approx. 8%)
  • the compound I or the oxime mixture described above, has special organoleptic properties which make it particularly suitable as a fragrance.
  • the invention accordingly relates to the use of the compound I or its mixture with the above acyclic oximes Ib-Id as a fragrance.
  • the oxime or oxime mixture according to the invention is distinguished by a special combination of valuable properties. It is colorless, easily accessible, the individual approaches are constant in smell, not irritating, stable and easy to use.
  • the compound of formula I has in particular the characteristic smell aspect of the fresh flowers of Salvia sclarea (clary sage), this smell is accompanied by herbaceous nuances.
  • Odor of the mixture of the acyclic oximes in the specified ratio i.e. the ratio obtained during production:
  • organoleptic properties of I are accordingly completely different from the organoleptic properties of this known oxime, and in particular also completely different from the olfactory properties of compound II: warm, spicy, peppery, camphorous, woody (see FR-A-2 433 941). Such an olfactory "shift” cannot be observed even in the case of the ketones / oximes of E-A-0 045 861.
  • Another important and typical property of the new oxime I according to the invention is its high integration capacity in the creation of perfume compositions.
  • the new oxime I develops its full effect particularly in the medium to volatile range of composition by enriching, harmonizing or harmonizing the desired odor complexes modified and fixed the same excellent.
  • 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 content of I in (new) perfumery bases can easily be up to 80% and in the perfumery compositions produced with it, up to 20-30% of this base can be used without problems to achieve the desired effects.
  • the experienced perfumer can already interest with concentrations of 0.1-0.5% achieve significant odor nuances so that the concentration used covers a fairly large area.
  • compositions made with I can be used for all types of perfumed consumer goods.
  • the compounds I can accordingly be used in the production of compositions and - as the above compilation shows - using a wide range of known fragrances.
  • 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.
  • the oxime product mixture thus obtained is separated into the individual constituents by column chromatography on a 100-fold amount of silica gel using hexane / ether 10: 1 as the eluent.
  • the "new compound I" is always understood to mean a mixture of I in combination with the acyclic oximes, as is e.g. is accessible according to Example I.
  • this flowery composition resembles lily-of-the-valley gains a radiance by now underlining the rhodinol note in the composition very advantageously and in harmony with the less volatile components.
  • a very natural-looking freshness aspect also gives the composition the impression of dewy flowers.

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)
  • Medicinal Preparation (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (4)

1. Composition de parfum, caractérisé en ce qu'elle comporte du 2-(1'-hydroximino-éthyl)-1,3,3,4,4-pentaméthyl-cyclopentène.
2. Composition de parfum, caractérisé en ce qu'elle comporte du 2-(1'-hydroximino-éthyl)-1,3,3,4,4-pentaméthyl-cyclopentène en combinaison avec la 3,5-diméthyl-3-(2'-méthyl-propène-1'-yl)-4-hexène-2- one oxime, la 5-méthylène-4,4,7-triméthyl-6-octène-2-one oxime et la 4,4,5,7-tétraméthyl-5,7-octadiène-2- one oxime.
3. Utilisation de 2-(1'-hydroximino-éthyl)-1,3,3,4,4-pentaméthyl-cyclopentène comme parfum.
4. Utilisation de 2-(1'-hydroximino-éthyl)-1,3,3,4,4-pentaméthyl-cyclopentène en combinaison avec la 3,5-diméthyl-3-(2'-méthyl-propène-1'-yl)-4-hexène-2-one oxime, la 5-méthylène-4,4,7-triméthyl-6-octène-2- one oxime et la 4,4,5,7-tétraméthyl-5,7-octadiène-2-one oxime comme parfum.
EP86112050A 1985-09-13 1986-09-01 Oxime cyclique Expired - Lifetime EP0214588B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3974/85 1985-09-13
CH397485 1985-09-13

Publications (3)

Publication Number Publication Date
EP0214588A2 EP0214588A2 (fr) 1987-03-18
EP0214588A3 EP0214588A3 (en) 1988-02-03
EP0214588B1 true EP0214588B1 (fr) 1990-09-26

Family

ID=4267438

Family Applications (1)

Application Number Title Priority Date Filing Date
EP86112050A Expired - Lifetime EP0214588B1 (fr) 1985-09-13 1986-09-01 Oxime cyclique

Country Status (4)

Country Link
US (1) US4678604A (fr)
EP (1) EP0214588B1 (fr)
JP (1) JPS6267060A (fr)
DE (1) DE3674517D1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0618897B1 (fr) * 1991-12-20 1997-09-17 Union Camp Corporation Composes nitrile et aldoxime indane, et leur emploi comme parfum
EP0672746B1 (fr) * 1994-03-18 2002-05-29 Givaudan SA Ethers d'oximes et compositions parfumantes et aromatisantes les contenant
MX2020003957A (es) * 2017-10-17 2020-08-03 S H Kelkar & Company Ltd Odorantes y composiciones que contienen olores.

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1205534B (de) * 1962-04-11 1965-11-25 Edison Soc Verfahren zur Herstellung von Cycloalkanonoximen mit 5 bis 12 Ring-kohlenstoffatomen
CH644757A5 (de) * 1978-08-21 1984-08-31 Givaudan & Cie Sa Riechstoffkompositionen.
DE3166476D1 (en) * 1980-08-08 1984-11-08 Givaudan & Cie Sa Unsaturated compounds, process for their preparation, their use as perfumes and the perfumed compositions containing them
DE3129934C2 (de) * 1981-07-29 1983-09-15 Dragoco Gerberding & Co Gmbh, 3450 Holzminden Verwendung von 1,5-Dymethyl-8-hydroximino-bicyclo[3.2.1]octan als Riech- und Aromastoff
EP0085352B1 (fr) * 1982-02-03 1986-01-22 L. GIVAUDAN & CIE Société Anonyme Oximes insaturées, leurs procédés de préparation et leur utilisation comme parfum et dans les compositions de parfum

Also Published As

Publication number Publication date
JPS6267060A (ja) 1987-03-26
DE3674517D1 (de) 1990-10-31
EP0214588A2 (fr) 1987-03-18
US4678604A (en) 1987-07-07
EP0214588A3 (en) 1988-02-03

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