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A green, lily of the valley perfuming ingredient

a perfuming ingredient and green lily of the valley technology, applied in the field of perfume, can solve the problems of no prior art document reporting or suggesting any organoleptic properties

Active Publication Date: 2018-10-04
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to the use of compounds of formula (I) as perfusing ingredients in perfumery. These compounds are novel and have not been previously reported in the prior art. The invention provides a new solution for creating perfumes with green, floral notes. The compounds have a unique structure and are useful in creating perfume compositions and consumer products with the desired odor notes.

Problems solved by technology

Therefore, none of these prior art documents reports or suggests any organoleptic properties of the compounds of formula (I), or any use of said compounds in the field of perfumery.

Method used

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  • A green, lily of the valley perfuming ingredient
  • A green, lily of the valley perfuming ingredient
  • A green, lily of the valley perfuming ingredient

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of Compounds of Formula (I)

a) Preparation of a Mixtures of 3-[5-(2-propanyl)-1-cyclohexen-1-yl]propanal and its Isomer 3-[3-(2-propanyl)-1-cyclohexen-1-yl]propanal

i) 7-isopropyl-1-oxaspiro[4.5]decan-2-one

[0070]3-isopropyl-1-cyclohexanol (140 g; 984 mmol; 2 eq.) was heated in an oil bath at 155° C. under nitrogen. Di-tert-butyl peroxide (18.36 g; 123 mmol; 0.25 eq.) and n-butyl acrylate (63.7 g; 492 mmol; 1 eq.) were added simultaneously and separately over a period of 1 hour. After 4 more hours at 150° C., the reaction was cooled to 50° C. and MTBE (100 mL) was added, followed by 30% aqueous NaOH solution (118 g; 886 mmol). After stirring for 30 minutes, water (140 mL) was added, followed by MTBE (140 mL). The phases were separated and the aq. phase was treated with diethyl ether (2×300 mL) and MTBE (300 mL). Each organic phase was treated with water (210 mL). The combined aqueous phases were treated with 50% aqueous H2SO4 solution (280 g), extracted twice with diethyl eth...

example 2

Preparation of a Perfuming Composition

[0095]A perfuming composition, of the floral type, was prepared by admixing the following ingredients:

Parts byweightIngredient100Acropal 1)40C 12 Aldehyde10C 8 Aldehyde501%* Cuminic aldehyde20(3,7-Dimethyl-6-octenyloxy)acetaldehyde209-Undecenal1000Coranol ®2)300Hivernal ®3)10003-(4-Isopropylphenyl)-2-methylpropanal5000Florol ®4)2010%* (4-methylphenoxy)acetaldehyde500Lilyflore ®5)300Mayol ®6)500(4E)-4-methyl-5-(4-methylphenyl)-4-pentenal5003 -(4,4-dimethyl-1-cyclohexen-1-yl)propanal1401%* Trans Decenal1007-(2-methyl-2-propanyl)-2H-1,5-benzodioxepin-3(4H)-one9600*in dipropyleneglycol1) 3 / 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde a)2) 4-cyclohexyl-2-methyl-2-butanol a)3) 3-(3,3 / 1,1-dimethyl-5-indanyl)propanal a)4) tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol a)5) (2,5-dimethyl-2,3-dihydro-1H-inden-2-yl)methanol a)6) cis-4-(1methylethyl)-cyclohexanemethanol a)a) origin: Firmenich SA, Geneva, Switzerland

[0096]The addition of 400 parts by w...

example 3

Preparation of a Perfuming Composition

[0099]A perfume, of the herbaceous, floral lily of the valley type, was prepared by admixing the following ingredients:

Parts byweightIngredient200Hexyl acetate500Isobornyl acetate100Geranyl acetate100Phenylethyl acetate50Styrallyl acetate400Verdyl acetate500Hexylcinnamic aldehyde1002-Methyl undecanal50Allyl Amyl Glycolate50Methyl anthranilate40Methyl benzoate250Benzylacetone150(1-Methyl-2-phenyl)ethyl butanoate107-Isopropyl-2H,4H-1,5-benzodioxepin-3-one100Cetalox ®1)30Raspberry ketone50Citronellyl Nitrile250Coumarine30Damascone Alpha600Dihydromyrcenol40Ethylvanilline100Eugenol300Fructalate ®2)400Gamma Undecalactone200Geraniol500Habanolide ®3)400Hedione ®4)100Allyl heptanoate100Ionone Beta300Iralia ®5)500Iso E ® Super 6)100Lavandin Grosso essential oil201-(2,2,3,6-Tetramethyl-cyclohexyl)-3-hexanol a)30Methyl Phenylethyl Ether502-Ethyl methylbutyrate20Methylparacresol30Crystal Moss oil100Muscenone ® Delta 7)20Neobutenone ® Alpha 8)100Nirvanol ®9)2...

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Abstract

The present invention concerns compound of formulain the form of any one of its stereoisomers or a mixture thereof, and wherein the exocyclic dotted line represents a carbon-carbon single or double bond, and one endocyclic dotted to line represents a carbon-carbon single bond and the other endocyclic dotted line represents a carbon-carbon double bond; and R, R1 and R2 represent, independently from each other, a hydrogen atom or a C1-3 alkyl group; and their use in perfumery to impart odor notes of the green, floral type.

Description

TECHNICAL FIELD[0001]The present invention relates to the field of perfumery. More particularly, it concerns the use as perfuming ingredient of compounds of formula (I) as defined below, which are useful perfuming ingredients of the green, floral type. Therefore, following what is mentioned herein, the present invention comprises the invention's compound as part of a perfuming composition or of a perfuming consumer product.PRIOR ART[0002]To the best of our knowledge, the compounds of formula (I) are novel.[0003]To the best of our knowledge, the prior art reports some structural analogues as perfuming ingredients.[0004]WO 08 / 053148 reports some cyclohexyl (i.e. saturated) analogues of the present invention which are described as having perfuming properties of the lily of the valley type. Said document does not suggest unsaturated compounds, and the only compounds having also green note do have a significantly different substitution pattern compared to the present ones.[0005]US 2009 / 0...

Claims

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Application Information

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IPC IPC(8): C11B9/00C07C47/225
CPCC11B9/0034C07C47/225C07C2601/16A61Q13/00
Inventor MORETTI, ROBERTBIRKBECK, ANTHONY ALEXANDER
Owner FIRMENICH SA
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