[go: up one dir, main page]

WO1999021847A1 - Nouveau compose de parfum - Google Patents

Nouveau compose de parfum Download PDF

Info

Publication number
WO1999021847A1
WO1999021847A1 PCT/GB1998/003129 GB9803129W WO9921847A1 WO 1999021847 A1 WO1999021847 A1 WO 1999021847A1 GB 9803129 W GB9803129 W GB 9803129W WO 9921847 A1 WO9921847 A1 WO 9921847A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
perfume
acetate
products
reaction
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.)
Ceased
Application number
PCT/GB1998/003129
Other languages
English (en)
Inventor
David Munro
Charles Stanley Sell
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 Nederland Services BV
Original Assignee
Quest International BV
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 Quest International BV filed Critical Quest International BV
Priority to AU95483/98A priority Critical patent/AU9548398A/en
Publication of WO1999021847A1 publication Critical patent/WO1999021847A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
    • 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
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms

Definitions

  • This invention concerns a novel fragrance compound, its method of production and its use in perfumes and perfumed products.
  • the invention provides 2-methylperhydro-as- ⁇ ndaceno [3a, 3-b] furan.
  • the compound is one of the minor products of Lewis acid-catalysed reaction of 1 ,5,9- cyclododecat ⁇ ene with propylene oxide, and can be separated and purified by chromatographic techniques
  • the reaction is preferably carried out at -70° C, using AICI 3 as the Lewis acid.
  • the invention provides a method of making the compound of the invention, comprising Lewis acid-catalysed reaction of 1 ,5,9- cyclododecat ⁇ ene with propylene oxide.
  • the compound of the invention exhibits an intense odour of blackcurrant or cassis of high impact and substantivity, and so may be used as such to impart, strengthen or improve the odour of a wide variety of products, or it may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume.
  • a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissoved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or any product for which an agreeable odour is indispensible or desirable.
  • Such products are: fabric washing powders, washing liquids, fabric softeners and other fabric care products; detergents and household cleaning, scouring and disinfection products; air fresheners, room sprays and pomanders; soaps, bath and shower gels, shampoos, hair conditioners and other personal cleansing products; cosmetics such as creams, ointments, toilet waters, preshave, aftershave, skin and other lotions, talcum powders, body deodorants and antiperspirants, etc.
  • fragrance materials which can be advantageously combined with the compound according to the invention in a perfume are, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.
  • fragrance materials are mentioned, for example, in S. Arctander, “Perfume and Flavor Chemicals” (Montclair, N.J., 1969), in S. Arctander, “Perfume and Flavor Materials of Natural Origin” (Elizabeth, N.J., 1960) and in “Flavor and Fragrance Materials - 1991", Allured Publishing Co. Wheaton, III. USA.
  • fragrance materials which can be used in combination with the compound according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citroneilyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethylphenylcarbinyl acetate, p-tert-butylcyclohexyl acetate, isononyl acetate
  • Solvents which can be used for perfumes which contain the compound according to the invention are, for example ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, t ⁇ ethyl citrate, isopropyl my ⁇ state, etc
  • the quantities in which the compound according to the invention can be used in perfumes or in products to be perfumed may vary within wide limits and depend, inter alia, on the nature of the product, on the nature and the quantity of the other components of the perfume in which the compound is used and on the olfactive effect desired It is therefore only possible to specify wide limits which, however, provide sufficient information for the specialist in the art to be able to use the compound according to the invention for his specific purpose
  • an amount of 0 01 % by weight or more of the compound according to the invention will generally have a clearly perceptible olfactive effect
  • the amount is 0 1 to 80% by weight, more preferably at least 1 %
  • the amount of the compound according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm However, levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed
  • the invention also covers a perfumed product comprising the compound of the invention
  • Figure 1 shows the structure of 2-methylperhydro-as- ⁇ ndaceno [3a,3-b] furan
  • Figure 2 shows the major products of Lewis acid-catalysed reaction of 1 ,5,9-cyclododecatr ⁇ ene with propylene oxide
  • Figure 3 illustrates the possibilities of double bond rearrangement and of internal ring closure of 1 ,5,9-cyclododecatr ⁇ ene and an ionic cascade reaction leading to production of the compound of the invention
  • the compound of the invention is associated with the furan fraction, and is a tetracyclic 5 furan formed in low yield (isolated in this example in ⁇ 0 1 % yield) by an ionic cascade reaction following formation of the initial carbonium ion, as shown in the reaction scheme of Figure 3.
  • Figure 3 also shows the possibilities of double bond rearrangement and of internal ring closure of 1 ,5,9-cyclododecatr ⁇ ene following formation of the initial carbonium ion, illustrated for attack to give the propan-2-ol side chain Reducing the reaction temperature to -70° C gives an increased yield of the compound of the invention, but remains only 1.6% (by glc), and extensive chromatographic purification is necessary to give a 0.5% isolated yield.
  • Experiments using SnCI 4 as catalyst failed to give any of the novel compound.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)

Abstract

L'invention concerne un nouveau composé 2-méthylperhydro-as-indaceno[3a,3-b] furane. Ce composé présente une forte odeur de cassis avec une affinité élevée. Il offre ainsi une grande utilité dans les parfums et les produits parfumés.
PCT/GB1998/003129 1997-10-28 1998-10-21 Nouveau compose de parfum Ceased WO1999021847A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU95483/98A AU9548398A (en) 1997-10-28 1998-10-21 Novel fragrance compound

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97308581 1997-10-28
EP97308581.4 1997-10-28

Publications (1)

Publication Number Publication Date
WO1999021847A1 true WO1999021847A1 (fr) 1999-05-06

Family

ID=8229574

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/003129 Ceased WO1999021847A1 (fr) 1997-10-28 1998-10-21 Nouveau compose de parfum

Country Status (2)

Country Link
AU (1) AU9548398A (fr)
WO (1) WO1999021847A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1252291A (fr) * 1968-07-23 1971-11-03

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1252291A (fr) * 1968-07-23 1971-11-03

Also Published As

Publication number Publication date
AU9548398A (en) 1999-05-17

Similar Documents

Publication Publication Date Title
WO1994013766A2 (fr) Esters d'acide dimethyl-cyclohexanecarboxylique en parfumerie
EP0819161B1 (fr) Substance de parfum
EP0841333A1 (fr) 14-Methyl-hexadecenolide et 14-methyl-hexadecanolide
US6559118B1 (en) Fragrance compounds
US5776884A (en) Cyclopentylidene-cyclopentanol in pereumery
US5849685A (en) Fragrance material
EP0770671B1 (fr) Cyclopentylidène-cyclopentanol en parfumerie
US7384905B2 (en) Pyridine derivates useful as fragrance materials
US5831101A (en) 14-methyl-hexadecenolide and 14-methyl-hexadecanolide
EP1087923B1 (fr) Nouveaux composes parfumes
WO1999021847A1 (fr) Nouveau compose de parfum
US5888961A (en) 1,3-dioxane and its use in perfumery
EP1399413B1 (fr) Composes aromatiques
EP1029845A1 (fr) 2-(4-Tert-pentylcyclohexyl)acétaldehyde et son utilisation comme agent parfumant
US20050148492A1 (en) Fragrance compounds
WO1999021813A1 (fr) Nouveau compose de parfum
EP0797569A1 (fr) Cyclohex(en)yl-propionitriles
WO1998009933A1 (fr) 2-cyclohexyl-propan-1-ol substitue et son utilisation dans des compositions pour parfums
EP1036792A1 (fr) Composé odorant
WO2000024705A1 (fr) Nitrile dienique et son utilisation dans les parfums
WO1999024386A1 (fr) Produits de reaction de prins de 5,7-dimethyl-oct-6-en-2-one et leur utilisation en tant que materiaux aromatiques
EP0967195A1 (fr) Cétones aldéhydiques et leur utilisation dans des parfums

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH GM HR HU ID IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT UA UG US UZ VN YU ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW SD SZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
NENP Non-entry into the national phase

Ref country code: KR

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

NENP Non-entry into the national phase

Ref country code: CA

122 Ep: pct application non-entry in european phase