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Perfuming ingredients of the floral and/or anis type

A compound, methyl technology, applied in the field of C12-C17 substituted derivatives

Inactive Publication Date: 2014-03-26
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] To the best of our knowledge, none of the known perfuming ingredients can be considered as close structural analogues

Method used

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  • Perfuming ingredients of the floral and/or anis type
  • Perfuming ingredients of the floral and/or anis type
  • Perfuming ingredients of the floral and/or anis type

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Synthesis of compounds of general formula (I)

[0074] 1-[(1E)-3-(allyloxy)-2-methyl-1-propenyl]-4-methylbenzene

[0075] Solid potassium tert-butyrate (47 g, 0.411 mol) was added portionwise to E-3-(4-methylphenyl)-2-methyl-2-propen-1-ol (68.05 g, 0.420mol) in dry THF (800ml) solution (exotherm to 30°C). After 1 hour at room temperature, the reaction was cooled to 5°C and tetrabutylammonium iodide (7.9 g, 0.021 mol) was added dropwise followed by allyl bromide (102.65 g, 0.840 mol). The reaction was warmed to room temperature overnight and poured into water (800ml). The reaction was extracted twice with ethyl acetate. Each organic phase was washed with water and brine. The combined extracts were dried over solid anhydrous sodium sulfate. The solid was filtered off, washed with diethyl ether and the solvent was removed under vacuum. The product was purified by distillation under vacuum through a 20 cm Widmer column. 79 g of the desired product were obtained (yi...

Embodiment 2

[0153] Preparation of Perfuming Compositions

[0154] A musk-herbal type cologne for men is prepared by mixing the following ingredients:

[0155]

[0156]

[0157] * in dipropylene glycol

[0158] ** in isopropyl myristate

[0159] 1) 8,12-Epoxy-13,14,15,16-destetramethylrebadan; source: Firmenich SA, Geneva, Switzerland

[0160] 2) 3-(4 / 2-ethylphenyl)-2,2-dimethylpropanal; source: International Flavors & Fragrances, USA

[0161] 3) 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran; source: International Flavors & Fragrances, USA

[0162] 4) cis-methyl dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0163] 5) (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate; source: Firmenich SA , Switzerland, Geneva

[0164] 6) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone; source: International Flavors & Fragrances, USA

[0165] 7) 3-(4-tert-Butylphenyl)-2-methylpropanal; Source: Givaudan SA, Geneva,...

Embodiment 3

[0170] Preparation of Perfuming Compositions

[0171] Prepare a floral-water cologne by mixing the following ingredients:

[0172]

[0173]

[0174] * in dipropylene glycol

[0175] ** in isopropyl myristate

[0176] 1) 2,6-Dimethyl-2-heptanol; source: Givaudan SA, Geneva, Switzerland

[0177] 2) Cyclopentadecanolide; Source: Firmenich SA, Geneva, Switzerland

[0178] 3) 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran; source: International Flavors & Fragrances, USA

[0179] 4) Methyl dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0180] 5) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone; source: International Flavors & Fragrances, USA

[0181] 6) 3-(4-tert-Butylphenyl)-2-methylpropanal; Source: Givaudan SA, Geneva, Switzerland

[0182] 7) 4 / 3-(4-Hydroxy-4-methylphenyl)-3-cyclohexene-1-carbaldehyde; source: International Flavors & Fragrances, USA

[0183] 8) (1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetic acid (+)-me...

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Abstract

The present invention concerns the use as perfuming ingredient, for instance to impart odor notes of the floral and / or green type, of a compound of formula 5 wherein R is an ortho, meta or para substituent of the phenyl, and represents a hydrogen atom or a C 1-2 alkyl or alkoxyl group; R 1 represents a hydrogen atom or a methyl or ethyl group; 10 R 2 represents a hydrogen atom or a C 1-3 alkyl group; and X represents a CHO, COOR 3, CH(OR 4) 2 or CN group, R 3 being a methyl or ethyl group, and R 4, taken seperately, being a methyl or ethyl group, or said R 4, taken together, a C 2-5 alkanediyl group; and at least one of said R, R 1 or R 2 represents a group containing at least one carbon atom.

Description

technical field [0001] The present invention relates to the field of spices, more specifically to the C of 3-phenyl-4-pentenal 12 ~C 17 substituted derivatives. [0002] The invention also relates to the use of said compounds in the fragrance industry, as well as compositions and articles containing said compounds, and some of said compounds. Background technique [0003] To our knowledge, none of the compounds of the present invention has been described as a perfuming ingredient. [0004] Among the compounds of the present invention, only 4-methyl-3-phenyl-4-pentenal (see J.A.C.S of K.Maruoka et al., 1994, 116 , 4131) and 2,4-dimethyl-3-phenyl-4-pentenal (see S.Gladiali et al. Chimica e Industria, 1981, 63 , 506) two known in the prior art. Both compounds are described as pure compounds and neither of these documents suggests that said compounds are used as perfuming ingredients. [0005] To our knowledge, none of the known perfuming ingredients can be considered as c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C11B9/00C07C47/232C07C47/277C07C45/29C07C45/51C07C69/618C07C67/27C07C255/33C07C253/02
CPCC07C47/277A61Q13/00A61Q5/02A61Q9/02C07C45/513C07C45/292C07C255/33C11B9/0065C07C47/232A61Q19/00C11B9/0061
Inventor R·莫雷蒂
Owner FIRMENICH SA
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