WO1999024386A1 - Produits de reaction de prins de 5,7-dimethyl-oct-6-en-2-one et leur utilisation en tant que materiaux aromatiques - Google Patents

Produits de reaction de prins de 5,7-dimethyl-oct-6-en-2-one et leur utilisation en tant que materiaux aromatiques Download PDF

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Publication number
WO1999024386A1
WO1999024386A1 PCT/GB1998/003309 GB9803309W WO9924386A1 WO 1999024386 A1 WO1999024386 A1 WO 1999024386A1 GB 9803309 W GB9803309 W GB 9803309W WO 9924386 A1 WO9924386 A1 WO 9924386A1
Authority
WO
WIPO (PCT)
Prior art keywords
products
odour
hexanone
dimethyl
acetate
Prior art date
Application number
PCT/GB1998/003309
Other languages
English (en)
Inventor
David Munro
Original Assignee
Quest International B.V.
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 B.V. filed Critical Quest International B.V.
Priority to AU97560/98A priority Critical patent/AU9756098A/en
Publication of WO1999024386A1 publication Critical patent/WO1999024386A1/fr

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
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D309/22—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • 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
    • C11B9/0003—Compounds of unspecified constitution defined by the chemical reaction for their preparation
    • 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 novel fragrance compounds, their method of production and their use in perfumes and perfumed products.
  • the present invention provides products of a Prins reaction on isoelgenone.
  • the resulting reaction mixture has a very noticeable strong odour reminiscent of cooked or stewed plum, and therefore contains materials with desirable organoleptic or odour properties.
  • Prins reaction see, for example, Adams and
  • the reaction mixture resulting from a Prins reaction of isoelgenone is a useful fragrance material in its own right.
  • Products or mixtures having the odour of plum separated or purified from the initial mixture, for example distillation fractions or chromatographically separated fractions, are also useful fragrance materials, as are the 2 major components noted above, 5-(4-methyl-3,6-dihydro-2H-5-pyranyl)-2 hexanone and 5-(4,4-dimethyl-1 ,3-dioxolan-5-yl)-2-hexanone.
  • the present invention therefore includes within its scope all such mixtures and products.
  • the invention thus provides 5-(4-methyl-3,6-dihydro-2H-5-pyranyl)-2 hexanone.
  • the invention also thus provides 5-(4,4-dimethyl-1 ,3-dioxolan-5-yl) -2-hexanone.
  • 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 products and mixtures 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, nitrites, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic and heterocyclic compounds.
  • fragrance materials which can be used in combination with the products and mixtures according to the invention are: geraniol, geranyl acetate, iinalol, linalyl acetate, tetrahydrolinaiol, citronellol, citronellyl 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
  • Solvents which can be used for perfumes which contain products and mixtures according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • the quantities in which products and mixtures 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 material is used and on the olfactive effect desired.
  • the invention thus provides a perfume comprising a product or mixture according to the invention in an oifactively effective amount.
  • the invention also covers a perfumed product comprising a product or mixture according to the invention.
  • Figure 1 is a reaction scheme for production of isoelgenone from pinanol.
  • reaction mixture was then quenched into a 50/50 mixture of H 2 0/Et 2 0 (800ml), and the organic layer was separated, washed with saturated NaHC0 3 (aq), then water, and dried over MgS0 4 .
  • the solvent was removed in vacuo to give a pale brown oil (41 g). This material was split into two 20g batches.

Landscapes

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

Abstract

Produits obtenus par réaction de Prins sur isoelgénone et présentant une forte odeur de prune cuite, ce qui permet de les utiliser dans des parfums et dans des produits parfumés. De nouveaux composés responsables de l'odeur de prune contiennent 5-(4-méthyl-3,6-dihydro-2H-5-pyranyl)-2-hexanone et 5-(4,4-diméthyl-1,3-dioxolane-5-yl)-2-hexanone (1).
PCT/GB1998/003309 1997-11-12 1998-11-04 Produits de reaction de prins de 5,7-dimethyl-oct-6-en-2-one et leur utilisation en tant que materiaux aromatiques WO1999024386A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU97560/98A AU9756098A (en) 1997-11-12 1998-11-04 Prins reaction products of 5,7-dimethyl-oct-6-en-2-one and their use as fragrance materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP97309100.2 1997-11-12
EP97309100 1997-11-12

Publications (1)

Publication Number Publication Date
WO1999024386A1 true WO1999024386A1 (fr) 1999-05-20

Family

ID=8229611

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1998/003309 WO1999024386A1 (fr) 1997-11-12 1998-11-04 Produits de reaction de prins de 5,7-dimethyl-oct-6-en-2-one et leur utilisation en tant que materiaux aromatiques

Country Status (2)

Country Link
AU (1) AU9756098A (fr)
WO (1) WO1999024386A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018833A2 (fr) * 1979-05-04 1980-11-12 BUSH BOAKE ALLEN Limited Composition de parfums
EP0021013A1 (fr) * 1979-06-21 1981-01-07 BASF Aktiengesellschaft Dérivés de pyrane 2,4-disubstitués, leur préparation et leur utilisation comme agents parfumants

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0018833A2 (fr) * 1979-05-04 1980-11-12 BUSH BOAKE ALLEN Limited Composition de parfums
EP0021013A1 (fr) * 1979-06-21 1981-01-07 BASF Aktiengesellschaft Dérivés de pyrane 2,4-disubstitués, leur préparation et leur utilisation comme agents parfumants

Also Published As

Publication number Publication date
AU9756098A (en) 1999-05-31

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