EP0045534B1 - Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same - Google Patents

Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same Download PDF

Info

Publication number
EP0045534B1
EP0045534B1 EP19810200744 EP81200744A EP0045534B1 EP 0045534 B1 EP0045534 B1 EP 0045534B1 EP 19810200744 EP19810200744 EP 19810200744 EP 81200744 A EP81200744 A EP 81200744A EP 0045534 B1 EP0045534 B1 EP 0045534B1
Authority
EP
European Patent Office
Prior art keywords
phenyl
hexyl ketone
same
compositions containing
perfume compositions
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
Application number
EP19810200744
Other languages
German (de)
French (fr)
Other versions
EP0045534A1 (en
Inventor
Bruno Maurer
Alan Francis Thomas
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 EP0045534A1 publication Critical patent/EP0045534A1/en
Application granted granted Critical
Publication of EP0045534B1 publication Critical patent/EP0045534B1/en
Expired 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
    • C11B9/0061Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • the invention relates to the field of perfumery. It more particularly relates to the use of phenyl-n-hexyl ketone as a perfuming ingredient for the preparation of perfumes and perfumed products. It also relates to a fragrance composition containing said phenyl-n-hexyl ketone as an odoriferous ingredient.
  • Phenyl-n-hexyl ketone is a known chemical entity, described in particular in Beestein 7, 337; however, the state of the art is silent as to its organoleptic properties.
  • this compound has very interesting olfactory properties and can therefore find wide use as an odoriferous ingredient in compositions of various kinds.
  • phenyl-n-hexyl ketone can be used to give interesting olfactory effects vary relatively widely. Thus, concentrations of approximately 0.5 to 1%, by weight, relative to the total weight of the composition considered can already produce marked effects when perfuming products such as soaps, shampoos or cosmetic articles for example.
  • a basic perfume composition of the "yellow narcissus" type was prepared by mixing the following ingredients (parts by weight): The addition to 85 g of the composition indicated above of 15 g of phenyl-n-hexyl ketone makes its odor more intense and more rounded by giving it a more natural and pleasant character.

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)
  • Cosmetics (AREA)

Description

L'invention se rapporte au domaine de la parfumerie. Elle a plus particulièrement pour objet l'utilisation de phényl-n-hexyl cétone à titre d'ingrédient parfumant pour la préparation de parfums et produits parfumés. Elle a également pour objet une composition parfumante contenant ladite phényl-n-hexyl cétone en tant qu'ingrédient odoriférant.The invention relates to the field of perfumery. It more particularly relates to the use of phenyl-n-hexyl ketone as a perfuming ingredient for the preparation of perfumes and perfumed products. It also relates to a fragrance composition containing said phenyl-n-hexyl ketone as an odoriferous ingredient.

La phényl-n-hexyl cétone est une entité chimique connue, décrite notamment dans Beil- stein 7, 337; cependant l'état de la technique est muet quant à ses propriétés organo- leptiques.Phenyl-n-hexyl ketone is a known chemical entity, described in particular in Beestein 7, 337; however, the state of the art is silent as to its organoleptic properties.

Il a été découvert que ce composé possède des propriétés olfactives fort intéressantes et peut de ce fait trouver une utilisation étendue en tant qu'ingrédient odoriférant dans des compositions de nature variée.It has been discovered that this compound has very interesting olfactory properties and can therefore find wide use as an odoriferous ingredient in compositions of various kinds.

Son odeur, de bonne puissance, est de type fleuri et rappelle l'odeur développée par certaines fleurs appartenant à famille des amaryllidacées, la jonquille ou le narcisse en particulier.Its scent, of good power, is of the flowery type and recalls the smell developed by certain flowers belonging to the amaryllidaceae family, the daffodil or the narcissus in particular.

Ses propriétés odoriférantes sont cependant nettement distinctes de celles exhibées par des produits analogues, telle la phényl-n-amyl cétone par exemple qui ne trouve qu'une utilisation limitée en parfumerie, en tant que modifac- teur de l'effet exercé par la combinaison coumarine-salicylate d'amyle dans des compositions de type fourgère (voir S. ARCTANDER: "Perfume and flavor chemicals", 1969, Mont- clair, N. J. (US), no. 211).Its odoriferous properties are however clearly distinct from those exhibited by analogous products, such as phenyl-n-amyl ketone for example which finds only limited use in perfumery, as a modifier of the effect exerted by the combination amyl coumarin-salicylate in fourger-type compositions (see S. ARCTANDER: "Perfume and flavor chemicals", 1969, Mont-clair, NJ (US), no. 211).

Les proportions dans lesquelles la phényl-n-hexyl cétone peut être utilisée pour donner des effets olfactifs intéressants varient de façon relativement étendue. C'est ainsi que des concentrations de 0,5 à 1% environ, en poids, par rapport au poids total de la composition considérée peuvent déjà produire des effets marqués lors du parfumage de produits tels que savons, shampoings ou articles cosmétiques par exemple.The proportions in which phenyl-n-hexyl ketone can be used to give interesting olfactory effects vary relatively widely. Thus, concentrations of approximately 0.5 to 1%, by weight, relative to the total weight of the composition considered can already produce marked effects when perfuming products such as soaps, shampoos or cosmetic articles for example.

Des proportions supérieures, allant jusqu'à 20% ou au-delà, peuvent par contre être utilisées pour la préparation de compositions ou bases parfumantes. Bien entendu, de telles limites de concentration ne sauraient être interprétées de façon restrictive car elles dépendent de la nature des coingrédients odorants de la compostion donnée ou de celle des articles que l'on désire parfumer.Higher proportions, up to 20% or more, can however be used for the preparation of perfume compositions or bases. Of course, such concentration limits should not be interpreted restrictively because they depend on the nature of the odorous co-ingredients of the given composition or on that of the articles which one wishes to perfume.

La phényl-n-hexyl cétone peut être préparée selon l'une des méthodes de synthèse courante, par exemple par acylation du benzène au moyen d'une réaction du type de Friedel-Crafts à l'aide de chlorure d'heptanoyle [voir par exemple: Organikum, Org. Chem. Grund-praktikum, Berlin (1964), p. 290]. Le produit ainsi obtenu possédait Eb. 85-90°/1 Pa. Ses'caractères analytiques étaient les suivants:

  • SM: 190 (M+, 5); m/e:105(100), 120(76), 77(43), 51 (10), 43(9), 106(7), 133(6), 121(6);
  • IR (liquide, film): 1675 cm i;
  • RMN (60 MHz, CDCI3): 0,89 (t, 3H); 1,0-2,0 (8H, bande large); 2,90 (2H, t, J=7 Hz); 7,2-7,5 (3H, m); 7,8-8,05 (2H, m) b ppm.
Phenyl-n-hexyl ketone can be prepared according to one of the current synthesis methods, for example by acylation of benzene by means of a Friedel-Crafts type reaction using heptanoyl chloride [see by example: Organikum, Org. Chem. Grund-praktikum, Berlin (1964), p. 290]. The product thus obtained possessed Eb. 85-90 ° / 1 Pa. Its analytical characteristics were as follows:
  • MS: 190 (M + , 5); m / e: 105 (100), 120 (76), 77 (43), 51 (10), 43 (9), 106 (7), 133 (6), 121 (6);
  • IR (liquid, film): 1675 cm i ;
  • NMR (60 MHz, CDCI 3 ): 0.89 (t, 3H); 1.0-2.0 (8H, broadband); 2.90 (2H, t, J = 7 Hz); 7.2-7.5 (3H, m); 7.8-8.05 (2H, m) b ppm.

L'exemple suivant est destiné à illustrer l'invention de façon plus détaillée, sans pour autant la limiter.The following example is intended to illustrate the invention in more detail, without however limiting it.

ExempleExample

Une composition parfumante de base de type "narcisse jaune" a été préparée en mélangeant les ingrédients suivants (parties en poids):

Figure imgb0001
L'adjonction à 85 g de la composition indiquée ci-dessus de 15 g de phényl-n-hexyl cétone rend son odeur plus intense et plus arrondie en lui conférant un caractère plus naturel et agréable.A basic perfume composition of the "yellow narcissus" type was prepared by mixing the following ingredients (parts by weight):
Figure imgb0001
The addition to 85 g of the composition indicated above of 15 g of phenyl-n-hexyl ketone makes its odor more intense and more rounded by giving it a more natural and pleasant character.

Claims (2)

1. Utilization of phenyl-n-hexyl ketone as perfuming ingredient for the preparation of perfumes and perfumed products.
2. Perfume composition containing phenyl-n-hexyl ketone as odoriferous ingredient.
EP19810200744 1980-07-31 1981-07-01 Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same Expired EP0045534B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH5833/80 1980-07-31
CH583380 1980-07-31

Publications (2)

Publication Number Publication Date
EP0045534A1 EP0045534A1 (en) 1982-02-10
EP0045534B1 true EP0045534B1 (en) 1983-12-21

Family

ID=4300055

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19810200744 Expired EP0045534B1 (en) 1980-07-31 1981-07-01 Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same

Country Status (3)

Country Link
EP (1) EP0045534B1 (en)
JP (1) JPS5754113A (en)
DE (1) DE3161699D1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3703584A1 (en) * 1987-02-06 1988-08-18 Consortium Elektrochem Ind ALDEHYDE AND ALCOHOLS WITH 3-METHYL OR 3,5-DIMETHYLPHENYL GROUPS, THE PRODUCTION AND USE THEREOF AS A PERFUME
DE60136178D1 (en) * 2000-06-15 2008-11-27 Firmenich & Cie USE OF KETONES AS PREVIEW OF ACTIVE COMPOUNDS
EP3870563A4 (en) * 2018-10-24 2022-08-10 International Flavors & Fragrances Inc. Novel organoleptic compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH583083A5 (en) * 1973-09-25 1976-12-31 Firmenich & Cie

Also Published As

Publication number Publication date
JPS5754113A (en) 1982-03-31
JPH0138160B2 (en) 1989-08-11
DE3161699D1 (en) 1984-01-26
EP0045534A1 (en) 1982-02-10

Similar Documents

Publication Publication Date Title
EP0056109B1 (en) Use of 2,6,6-trimethyl-cyclohex-2-ene-1-yl-carboxylic-acid methyl ester as a perfuming agent
EP0180885B1 (en) Use of a cycloaliphatic carbinol as a perfuming ingredient
EP0584477B1 (en) Use of a cyclopentadecenone as a perfuming ingredient
EP0045534B1 (en) Use of phenyl-n-hexyl ketone as a perfuming agent, and perfume compositions containing the same
EP0482385A1 (en) (2E,4Z,7Z)-ethyl decatrienoate and its use as a perfuming and flavouring ingredient
EP0115278B1 (en) Use of 1-cyclopentenylacetic acid as perfuming ingredient, perfuming composition containing it and perfumed products
EP0982295A2 (en) Ethers; their use as perfuming or flavouring agents; their preparation
EP0051546B1 (en) Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained
CH616585A5 (en)
EP0809485B1 (en) Use of 4-tert-butyl-1-cyclohexanol as an antioxidant
EP0544110A1 (en) Tertiary cyclic alcools and their use as perfume component
EP0688856B1 (en) Use of an alkyl substituted pyridine as perfuming ingredient
JP2002514681A (en) Fragrance composition
EP0081699B1 (en) Alicyclic compounds, their use as perfume or flavouring agents and process for their preparation
EP0916650B1 (en) Nitriles and aldehydes derived from 3-isopropenyl-1,2-dimethyl-1-cyclopentanol and their use in perfumery
EP1069176B1 (en) Aliphatic esters and their use as perfume ingredients
CN100509749C (en) Fragrance compound
EP0080600B1 (en) Use of 2-hydroxy-3,4,4-trimethyl-cyclopent-2-ene-1-one as odorant ingredient
EP0050577B1 (en) Process for preparing perfuming compositions and perfumed products, and compositions and products so obtained
US4031034A (en) Altering perfume green notes using trithioacetone
EP0181475B1 (en) Unsaturated aliphatic ketone and its use as perfuming ingredient
EP0056500A2 (en) 2,2-Dimethyl-propionic acid esters, their use as perfuming agents and composition containing one of them
EP0504563B1 (en) Perfuming ingredient with a spiranic structure
CH636009A5 (en) USE OF A HYDROXY-ACETYLENIC DERIVATIVE AS A PERFUMING INGREDIENT.
EP0052115B1 (en) Bicyclic compounds and utilization thereof as perfuming agents

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

AK Designated contracting states

Designated state(s): CH DE FR GB NL

17P Request for examination filed

Effective date: 19820706

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

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

REF Corresponds to:

Ref document number: 3161699

Country of ref document: DE

Date of ref document: 19840126

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

Ref country code: NL

Payment date: 19840731

Year of fee payment: 4

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

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

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19860201

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19910628

Year of fee payment: 11

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

Ref country code: DE

Effective date: 19930401

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

Ref country code: FR

Payment date: 19940609

Year of fee payment: 14

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

Ref country code: GB

Payment date: 19940620

Year of fee payment: 14

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

Ref country code: CH

Payment date: 19940725

Year of fee payment: 14

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

Ref country code: GB

Effective date: 19950701

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

Ref country code: LI

Effective date: 19950731

Ref country code: CH

Effective date: 19950731

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19950701

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

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

Ref country code: FR

Effective date: 19960430

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST