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

Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen Download PDF

Info

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
Authority
EP
European Patent Office
Prior art keywords
olide
pentadec
weight
mixture
product
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
EP19900119869
Other languages
English (en)
French (fr)
Other versions
EP0424787A3 (en
EP0424787A2 (de
Inventor
Peter Fankhauser
Piero C/O Prof. Wenkert Lab. Fantini
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=4265790&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=EP0424787(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Firmenich SA filed Critical Firmenich SA
Publication of EP0424787A2 publication Critical patent/EP0424787A2/de
Publication of EP0424787A3 publication Critical patent/EP0424787A3/fr
Application granted granted Critical
Publication of EP0424787B1 publication Critical patent/EP0424787B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B9/00Essential oils; Perfumes
    • C11B9/0069Heterocyclic compounds
    • C11B9/0073Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0084Heterocyclic 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.

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)
  • Detergent Compositions (AREA)
  • Cosmetics (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
CH3894/89 1989-10-27
CH389489 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)

Country Link
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
DE59804713D1 (de) 1997-10-09 2002-08-14 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
WO2005113533A1 (en) * 2004-05-13 2005-12-01 Symrise Gmbh & Co. Kg Process for preparing unsaturated lactones
DE112006002818B4 (de) 2005-11-09 2016-08-25 Symrise Ag Verfahren zur Herstellung von (10/11/12)-Pentadecen-15-olid ausgehend von 11- und/oder 12-Pentadecen-15-olid
KR101655082B1 (ko) * 2016-03-11 2016-09-22 (주)화진테크놀로지 필름 절단용금형
CN111936608B (zh) * 2018-04-02 2024-01-09 花王株式会社 麝香味组合物
EP4312962A1 (de) * 2021-05-20 2024-02-07 Firmenich SA Makrocyclen mit moschusartigem puder

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
DE2065550C2 (de) * 1969-05-29 1982-05-06 Firmenich S.A., 1211 Genève Verfahren zur Herstellung von bicyclischen Äthern und 13-Oxa-Bicyclo[10.4.0]Hexadecen[1(12)]
JPS5837900B2 (ja) * 1977-06-21 1983-08-19 オ−エンス・コ−ニング フアイバ−グラス コ−ポレ−シヨン 積層断熱マットを製造する方法および装置
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
EP0424787A3 (en) 1991-10-23
DE69028755T2 (de) 1997-06-05
EP0424787A2 (de) 1991-05-02
JPH03167295A (ja) 1991-07-19
JP3040449B2 (ja) 2000-05-15

Similar Documents

Publication Publication Date Title
EP0424787B1 (de) Verwendung von ungesättigten macrocyclischen Ketonen sowie Parfumingredienzen
EP0694605B1 (de) Cyclischer Diester und Verwendung desselben als Duftstoff
US5266559A (en) Use of unsaturated macrocyclic lactones as perfuming ingredients
EP0584477B1 (de) Verwendung einer Cyclopentadecenone als Parfümszutat
EP0621892B1 (de) Verwendung von Furanonen wie Duftstoffe
EP0465936B1 (de) Decalinylketonen, ihre Verwendung in der Parfümerie und Verfahren zu deren Herstellung
EP0504592B1 (de) Campholenstruktureinheit enthaltender Tertiäralkohol und dessen Anwendung als Duftstoff
EP0544110A1 (de) Tertiäre cyclische Alkohole und ihre Anwendung als Riechstoffbestandteile
EP0707575B1 (de) Verwendung von dihydrobenzofuranonen als parfüminhaltstoffe
EP0449034B1 (de) Cyclische Ketone, Verfahren zu deren Herstellung und deren Verwendung als Riechstoffe
EP0882697B1 (de) Riechstoffe mit holzartigen und fruchtartigen Geruchsnoten
EP0382934B1 (de) Tricyclische Ketone, Verfahren zu deren Herstellung und deren Anwendung als Riechstoffe
EP0572797B1 (de) Ungesättigte cyclische Alkohole, ihre Anwendung als Riechstoffbestandteile und deren Zwischenprodukte
EP0282798B1 (de) Aliphatische bicyclische Alkohole und ihre Anwendung als Riechstoffe
EP0664286B1 (de) Tetralinnitrile, ihre Verwendung als Inhaltsstoffe von Parfümen und Oximzwischenprodukte für ihre Herstellung
EP0838215B1 (de) Verwendung von ungesättigten aliphatischen Estern in der Parfümerie
CH685390A5 (fr) Composés furaniques et leur utilisation à titre d'ingrédients parfumants.
EP0504563B1 (de) Geruchsstoff mit einer Spiranstruktur
WO1992003402A1 (fr) Compose cetonique polycyclique et son utilisation a titre d'ingredient parfumant
CH680853A5 (en) New (plus)-(R)-1,4-di:methyl-3-cyclohexene-1-carboxylate - useful perfume ingredient e.g. in soap, shampoo, cosmetics, etc.
CH626533A5 (de)
EP0558928B1 (de) Furanether und ihre Anwendung als Riechstoffe
EP0052115B1 (de) Bicyclische verbindungen und ihre verwendung als riechstoffe
CH673116A5 (de)
EP0148399B1 (de) Polycyclischer Alkohol, Verfahren zu seiner Herstellung als duftender Bestandteil und eine diesen enthaltende Zusammensetzung

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19901108

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): CH DE FR GB LI NL

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): CH DE FR GB LI NL

17Q First examination report despatched

Effective date: 19931011

GRAG Despatch of communication of intention to grant

Free format text: ORIGINAL CODE: EPIDOS AGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAH Despatch of communication of intention to grant a patent

Free format text: ORIGINAL CODE: EPIDOS IGRA

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): CH DE FR GB LI NL

REF Corresponds to:

Ref document number: 69028755

Country of ref document: DE

Date of ref document: 19961107

GBT Gb: translation of ep patent filed (gb section 77(6)(a)/1977)

Effective date: 19961230

PLBI Opposition filed

Free format text: ORIGINAL CODE: 0009260

26 Opposition filed

Opponent name: BAYER AG

Effective date: 19970702

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

NLR1 Nl: opposition has been filed with the epo

Opponent name: BAYER AG

PLBF Reply of patent proprietor to notice(s) of opposition

Free format text: ORIGINAL CODE: EPIDOS OBSO

PLBL Opposition procedure terminated

Free format text: ORIGINAL CODE: EPIDOS OPPC

PLBM Termination of opposition procedure: date of legal effect published

Free format text: ORIGINAL CODE: 0009276

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: OPPOSITION PROCEDURE CLOSED

27C Opposition proceedings terminated

Effective date: 19980504

NLR2 Nl: decision of opposition
REG Reference to a national code

Ref country code: GB

Ref legal event code: IF02

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 20041102

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051031

Ref country code: CH

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20051031

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 20091026

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 20091016

Year of fee payment: 20

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 20091022

Year of fee payment: 20

Ref country code: FR

Payment date: 20091110

Year of fee payment: 20

REG Reference to a national code

Ref country code: GB

Ref legal event code: PE20

Expiry date: 20101016

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20101016

REG Reference to a national code

Ref country code: NL

Ref legal event code: V4

Effective date: 20101017

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Free format text: LAPSE BECAUSE OF EXPIRATION OF PROTECTION

Effective date: 20101017