EP0424787B1 - Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen - Google Patents

Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen Download PDF

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Publication number
EP0424787B1
EP0424787B1 EP19900119869 EP90119869A EP0424787B1 EP 0424787 B1 EP0424787 B1 EP 0424787B1 EP 19900119869 EP19900119869 EP 19900119869 EP 90119869 A EP90119869 A EP 90119869A EP 0424787 B1 EP0424787 B1 EP 0424787B1
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European Patent Office
Prior art keywords
olide
pentadec
weight
mixture
product
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Expired - Lifetime
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EP19900119869
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English (en)
French (fr)
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EP0424787A2 (de
EP0424787A3 (en
Inventor
Peter Fankhauser
Piero C/O Prof. Wenkert Lab. Fantini
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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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0084—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing more than six atoms

Definitions

  • the present invention relates to the field of perfumery. It relates more particularly to the use as perfuming ingredient of at least one pentadecenolide of formula having a trans configuration double bond in one of positions 11 or 12 as indicated by the dotted lines.
  • the above-mentioned compounds are unsaturated macrocyclic lactones whose chemical structure is known. They have, in fact, been cited as secondary or intermediate products of a process for the preparation of odoriferous saturated macrolides such as pentadecanolide, known under the trade name of EXALTOLIDE® (origin: Geneva, Switzerland), and the like [see, for example, French Patent FR-A-2,043,784 or J. Becker and G. Ohloff, Helv. Chim. Acta 54 , 2889 (1971)].
  • an appropriate peroxide was split by means of thermal energy or radiation, or else chemical agents, to obtain a mixture containing the desired saturated lactones, as well as the corresponding unsaturated lactones.
  • the saturated lactones were then either separated from this mixture by the usual separation techniques, or obtained by hydrogenation of said mixture or of the unsaturated lactones contained.
  • the unsaturated lactones and in particular those of trans configuration mentioned above, namely the trans-pentadec-12-en-15-olide and trans-pentadec-11-en-15-olide, have properties very interesting odorants and that they can therefore be used advantageously for the preparation of perfume compositions and perfumed products.
  • these lactones and their mixtures are used to develop fragrant notes of musk, animal type, very powerful and very effective for notes of this type, the smell of trans-pentadec-11-en-15-olide being however less potent than that of trans-pentadec-12-en-15-olide.
  • the latter also has a more marked musk-ambrette and fruity-pear connotation and is preferred according to the invention.
  • pentadecanolide Compared to their saturated analogue, namely pentadecanolide or EXALTOLIDE®, the aforementioned pentadecenolides, as well as their mixtures, have clearly more animal-like fragrant notes, with a connotation reminiscent of natural musk. In addition, they have the advantage of having fragrant notes whose power, volume and tenacity are much higher than those of the fragrant note characterizing pentadecanolide.
  • the compounds of formula (I) have odorous notes which are distinct from those of their isomers represented by the formula having a double bond of cis configuration in one of the positions 11 or 12 as indicated by the dotted lines.
  • the latter present, in fact, musky-type olfactory notes, less animal and elegant, as well as less powerful, than those of the corresponding trans-pentadecenolides (I).
  • the abovementioned unsaturated macrocyclic lactones can be used in perfumery in very varied applications. They lend themselves as well to the preparation of perfumes and colognes, as to the scenting of functional products such as soaps, shower or bath gels, shampoos, body or room air fresheners, cosmetic products and cleaning products. Due to the substantiality of their rating, they prove to be particularly advantageous for the perfuming of detergents or textile conditioners.
  • these unsaturated lactones can be used in the pure state or in a mixture with one or more perfuming ingredients, solvents or usual supports.
  • these pentadecenolides combine very harmoniously with one another, or else with the corresponding saturated lactone already mentioned, namely pentadecanolide.
  • the mixtures of trans-pentadec-11-en-15-olide and trans-pentadec-12-en-15-olide may contain relative proportions of these two lactones varying over a very wide range of values.
  • trans-pentadec-11-en-15-olide and trans-pentadec-12-en-15-olide, or their mixtures, can be used for the perfume applications according to the invention.
  • concentrations of the order of 1 to 10%, or even 20% by weight, relative to the weight of composition in which these lactones are incorporated can be used. These concentrations may be lower than the values quoted when perfuming articles such as soaps and shower or bath gels, shampoos, cosmetic products or detergents or textile conditioners.
  • the aforementioned unsaturated macrocyclic lactones can be prepared from 2- (3-hydroxypropyl) -1-cyclododecanone (the preparation of which is described in patent FR-A-2 043 784 cited above) according to a process analogous to that described by SL Schreiber and aI. in J. Am. Chem. Soc. 102 , 6163 (1980) and 107 , 2980 (1985) for the preparation of macrolides.
  • the specific conditions for the preparation of these lactones were as follows.
  • trans-pentadec-11-en-15-olide trans-pentadec-12-en-15-olide, as well as their mixtures according to the invention, are designated under the generic name of (E, Z ) -pentadéc-11 (12) -én-15-olide.
  • a basic musk-type perfume composition was prepared for a masculine cologne by mixing the following ingredients:
  • composition A 400 parts by weight of (E, Z) -pentadec-11 (12) -en-15-olide were added on the one hand to prepare a new composition A and, on the other hand, 400 parts by weight of EXALTOLIDE® to prepare a composition B.
  • Compositions A and B were evaluated by a panel of expert perfumers. In the unanimous opinion of the latter, composition A had a much more musky, animal and powerful fragrant note than that of composition B.

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  • 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)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Pyrane Compounds (AREA)

Claims (9)

  1. Gemisch, enthaltend mindestens 60 Gew.%, bezogen auf das Gewicht des Gemisches, Pentadecenolide der Formel
    Figure imgb0007
     welche eine Doppelbindung der Konfiguration E in einer der Stellungen 11 oder 12 besitzen, welche durch punktierte Linien angezeigt sind, begleitet von geringen Anteilen ihrer Isomeren der Formel
    Figure imgb0008
     welche eine Doppelbindung der Konfiguration Z in einer der Stellungen 11 oder 12 besitzen, welche durch punktierte Linien angezeigt sind.
  2. Gemisch gemäss Patentanspruch 1, dadurch gekennzeichnet, dass es 70 Gew.% und mehr Pentadecenolide der Formel (I) enthält.
  3. Gemisch gemäss den Patentansprüchen 1 oder 2, dadurch gekennzeichnet, dass es äquivalente Anteile von (E)-Pentadec-12-en-15-olid und (E)-Pentadec-11-en-15-olid oder einen Überschuss des ersteren enthält.
  4. Gemisch gemäss einem der Patentansprüche 1 bis 3, dadurch gekennzeichnet, dass es zusätzlich Pentadecanolid enthält.
  5. Gemisch gemäss Patentanspruch 4, dadurch gekennzeichnet, dass es ca. 43 Gew.% (E)-Pentadec-11-en-15-olid, 26 Gew.% (E)-Pentadec-12-en-15-olid, 18 Gew.% (Z)-Pentadec-11-en-15-olid, 5 Gew.% (Z)-Pentadec-12-en-15-olid und 8 Gew.% Pentadecanolid enthält.
  6. Riechstoffzusammensetzung oder parfümiertes Produkt, enthaltend als Riechstoffbestandteil ein Gemisch gemäss einem der Patentansprüche 1 bis 5.
  7. Als parfümiertes Produkt gemäss Patentanspruch 6, ein Parfüm oder ein Toilettwasser, eine Seife, ein Douche- oder Badegel, ein Shampoo, ein kosmetisches Erzeugnis, ein Körperdesodorant oder ein Raumluftverbesserer, ein Reinigungsmittel oder ein Textilauffrischungsmittel oder ein Pflegemittel.
  8. Verwendung eines Gemisches gemäss einem der Patentansprüche 1 bis 5 als Parfümbestandteil für die Herstellung einer Riechstoffzusammensetzung oder eines parfümierten Produktes.
  9. Verwendung gemäss Patentanspruch 8, dadurch gekennzeichnet, dass man dieses Gemisch der zu parfümierenden Zusammensetzung oder dem zu parfümierenden Produkt in genügender Menge zusetzt, um ihnen eine Duftnote vom Typ moschus-ambrette und fruchtig-birnenartig zu verleihen.
EP19900119869 1989-10-27 1990-10-17 Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen Expired - Lifetime EP0424787B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH389489 1989-10-27
CH3894/89 1989-10-27

Publications (3)

Publication Number Publication Date
EP0424787A2 EP0424787A2 (de) 1991-05-02
EP0424787A3 EP0424787A3 (en) 1991-10-23
EP0424787B1 true EP0424787B1 (de) 1996-10-02

Family

ID=4265790

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19900119869 Expired - Lifetime EP0424787B1 (de) 1989-10-27 1990-10-17 Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen

Country Status (3)

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EP (1) EP0424787B1 (de)
JP (1) JP3040449B2 (de)
DE (1) DE69028755T2 (de)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014040636A1 (de) 2012-09-14 2014-03-20 Symrise Ag Ungesättigte lactone als riechstoffe
WO2024022574A1 (en) * 2022-07-26 2024-02-01 Symrise Ag Biotechnological production of macrocyclic lactones

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5792740A (en) * 1996-03-08 1998-08-11 Firmenich Sa Fragrant macrocyclic lactones
DE19708924A1 (de) * 1997-03-05 1998-09-10 Haarmann & Reimer Gmbh Verwendung makrocyclischer Lactone als Riechstoffe
EP0908455B1 (de) * 1997-10-09 2002-07-10 Givaudan SA Macrocyclen
DE10152992A1 (de) * 2001-10-26 2003-05-08 Haarmann & Reimer Gmbh Gemische zur Verwendung als Moschusriechstoff
DE10152990A1 (de) * 2001-10-26 2003-05-08 Haarmann & Reimer Gmbh Gemische zur Verwendung als Moschusriechstoff
DE10227483A1 (de) 2002-06-19 2004-01-08 Symrise Gmbh & Co. Kg Verfahren zur Herstellung von 11(12)-Pentadecen-15-oliden
DE10348168A1 (de) * 2003-10-16 2005-05-12 Symrise Gmbh & Co Kg Verfahren zur Herstellung von 1-Hydroperoxy-16-oxabicyclo[40.4.0]hexadecan
ATE440831T1 (de) * 2004-05-13 2009-09-15 Symrise Gmbh & Co Kg Verfahren zur herstellung von ungesättigten lactonen
WO2007054429A1 (en) 2005-11-09 2007-05-18 Symrise Gmbh & Co. Kg Process for the production of (10/11/12)-pentadecen-15-olide starting from 11- and/or 12-pentadecen-15-olide
KR101655082B1 (ko) * 2016-03-11 2016-09-22 (주)화진테크놀로지 필름 절단용금형
US11352588B2 (en) * 2018-04-02 2022-06-07 Kao Corporation Musk-like composition
CN117320686A (zh) * 2021-05-20 2023-12-29 弗门尼舍有限公司 粉香、麝香气味剂大环

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB922409A (en) * 1960-04-08 1963-04-03 Boake Roberts & Co Ltd Macrocyclic lactones
DE2065551C3 (de) * 1969-05-29 1980-07-03 Firmenich S.A., Genf (Schweiz) Verfahren zur Herstellung von Lactonen mit 14 bis 17 Ringkohlenstoffatomen
BE868271A (fr) * 1977-06-21 1978-10-16 Owens Corning Fiberglass Corp Procede et appareil pour produire une nappe stratifiee
US4568470A (en) * 1983-07-18 1986-02-04 International Flavors & Fragrances Inc. Use of macrocyclic lactone in augmenting or enhancing aroma or taste of consumable materials

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014040636A1 (de) 2012-09-14 2014-03-20 Symrise Ag Ungesättigte lactone als riechstoffe
WO2024022574A1 (en) * 2022-07-26 2024-02-01 Symrise Ag Biotechnological production of macrocyclic lactones

Also Published As

Publication number Publication date
DE69028755D1 (de) 1996-11-07
DE69028755T2 (de) 1997-06-05
JP3040449B2 (ja) 2000-05-15
EP0424787A2 (de) 1991-05-02
EP0424787A3 (en) 1991-10-23
JPH03167295A (ja) 1991-07-19

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