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Pyran as floral odorant

A dotted line, compound technology, applied in lily-of-the-valley-type fragrance ingredients, floral fragrance field, can solve the problems of no reported or implied sensory properties, no reported or implied compound application, etc.

Active Publication Date: 2015-09-16
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] These prior art documents do not report or suggest any organoleptic properties of the compounds of formula (I) or formula (II), and do not report or suggest any application of said compounds in the field of fragrances

Method used

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  • Pyran as floral odorant
  • Pyran as floral odorant
  • Pyran as floral odorant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of Compounds of Formula (I)

[0067] Contains 88% of 4-(4-hydroxy-4-methylpentyl)-3,6-dihydro-2H-pyran-2-carbaldehyde and 12% of 5-(4-hydroxy-4-methylpentyl)-3,6-dihydro-2H-pyran-2-carbaldehyde The composition of (also referred to as composition 1)

[0068] a) ethyl 4-(4-hydroxy-4-methylpentyl)-3,6-dihydro-2H-pyran-2-carboxylate (as main compound) and 5-(4-hydroxy-4- Methylpentyl)-3,6-dihydro-2H-pyran-2-carboxylic acid ethyl ester (as a minor compound)

[0069] A mixture of ethyl glyoxylate (50% in toluene) (38.6 mL, 194 mmol) and myrcenol (20 g, 130 mmol) was heated at reflux for 29 hours. Excess ethyl glyoxylate and toluene were evaporated and the residue was purified by column chromatography on silica gel using a gradient mixture of heptane and ethyl acetate (85:15 to 60:40) to give the pure ester (80% yield ), a colorless oil and an 88:12 mixture of regioisomers.

[0070] Major isomer:

[0071] 1 H NMR: 5.44(m,1H),4.36(m,1H),4.18-4.28(m,4H),2....

Embodiment 2

[0084] Preparation of Perfuming Compositions

[0085] A woody-citrus type cologne for men was prepared by mixing the following ingredients:

[0086]

[0087]

[0088] *in dipropylene glycol

[0089] 1) Pentadecenolactone; Source: Firmenich SA, Geneva, Switzerland

[0090] 2) Compounded perfume base; source: Firmenich SA, Geneva, Switzerland

[0091] 3) Methyl (1R)-cis-3-oxo-2-pentyl-1-cyclopentaneacetate; source: Firmenich SA, Geneva, Switzerland

[0092] 4) 5-(2,2,3-Trimethyl-3-cyclopentenyl)-3-methylpentan-2-ol; source: Givaudan SA, Vernier, Switzerland

[0093] 5) Propyl (S)-2-(1,1-dimethylpropoxy)propionate; source: Firmenich SA, Geneva, Switzerland

[0094] 6) Methyl cedryl ketone; source: International Flavors&Fragrances, USA

[0095] 7) (1S,2S,3S)-2,6,6-Trimethyl-bicyclo[3.1.1]heptane-3-spiro-2'-cyclohexen-4'-one; Source: Firmenich SA, Geneva,Switzerland

[0096] The addition of 400 parts by weight of Composition 1 (as described in Example 1) to the above...

Embodiment 3

[0098] Preparation of Perfuming Compositions

[0099] A floral, fruity, violet type perfuming composition was prepared by mixing the following ingredients:

[0100]

[0101]

[0102]

[0103] *in dipropylene glycol

[0104] **in isopropyl myristate

[0105] 1) 16-Hexadecanolide; Source: Firmenich SA, Geneva, Switzerland

[0106] 2) Pentadecalactone; Source: Firmenich SA, Geneva, Switzerland

[0107] 3) Tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol; source: Firmenich SA, Geneva, Switzerland

[0108] 4) 1,3,4,6,7,8-Hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyran; source: International Flavors&Fragrances, USA

[0109] 5) Pentadecyl ester; source: Firmenich SA, Geneva, Switzerland

[0110] 6) cis-methyl dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0111] 7) (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate; source: Firmenich SA ,Geneva,Switzerland

[0112] 8) 3-(3,3 / 1,1-dimethyl-5-indanyl)propionaldehyde; s...

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Abstract

The present invention relates to a composition of matter comprising 1) at least 70 % of at least a compound of formula (I) in the form of any one of its stereoisomers or a mixture thereof, and wherein R represents - a hydrogen atom and the dotted line represents a carbon-carbon single or double bond; or - a CH2 group bonded with C4 and C5 and the dotted line represents a carbon-carbon single bond; 2) at most 30% of at least a compound of formula (II) in the form of any one of its stereoisomers or a mixture thereof, and wherein R represents - a hydrogen atom and the dotted line represents a carbon-carbon single or double bond; or - a CH2 group bonded with C4 and C5 and the dotted line represents a carbon-carbon single bond; and wherein the percentages are w / w percentages relative to the total weight of the composition. Said compositions are useful perfuming ingredients of the floral, lily of the valley type.

Description

technical field [0001] The present invention relates to the field of fragrances. More specifically, the present invention relates to the use of compositions of matter comprising derivatives of formula (I) and / or formula (II) as defined below as perfuming ingredients, which are useful perfuming ingredients of the floral, lily-of-the-valley type. Thus, as referred to herein below, the present invention comprises the compounds of the invention as part of a perfuming composition or a perfuming consumer product. Background technique [0002] To the best of our knowledge, the compounds of formula (I) of the present invention are novel. [0003] As far as we know, the closest analogues known in spices are described in US 2947780 as (4-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde plus isomer 3-(4-hydroxy-4-methylpentyl)-3 - Cyclohexene-1-carbaldehyde; source: International Flavors & Fragrances, Inc., New York, USA) known chemical. In addition, US 4007137 clearly show...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/06A61Q13/00C07D309/26
CPCC07D309/26C11B9/008C07D309/06A61K8/498A61Q5/06A61Q15/00C11D3/2096C11D3/50
Inventor J·库仑
Owner FIRMENICH SA
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