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Musk odorant with aromatic notes

A technology of methyl and naphthalenone, applied in the field of flavoring ingredients, penta/hexamethyl-3,4,5,8-tetrahydro-1-naphthone derivatives, can solve the sensory properties that have not been reported or suggested, There are no reports or hints about the application of the compound, etc.

Inactive Publication Date: 2014-03-19
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These prior art documents do not report or suggest any organoleptic properties of the compounds of general formula (I) discussed further below, nor do they report or suggest any application of said compounds in the field of fragrances

Method used

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  • Musk odorant with aromatic notes
  • Musk odorant with aromatic notes
  • Musk odorant with aromatic notes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Synthesis of compounds of general formula (I)

[0049] -Methyl 2,3,3,6,6-pentamethyl-4-oxocyclohex-1-enecarboxylate (2a)

[0050] A solution of tBuOK (16.28 g in 70 ml diglyme) and MeI (11.32 ml) were added simultaneously over 1.5 h to 2,6,6-trimethyl-4-oxocyclohexyl-2 cooled to 0°C In a solution of methyl-enecarboxylate (15g, 72.7mmol) in diglyme (80ml). The mixture was stirred at 0 °C for 2 hours, then quenched with 5% HCl. with Et 2 O extract the mixture and water, saturated NH 4 The organic layer was washed with OH solution, water, saturated bicarbonate solution and brine. with MgSO 4 The collected organic layers were dried, and the solvent was distilled off. The crude product was purified by distillation (125 °C, 0.1 mbar) and column chromatography (silica gel, cyclohexane / EtOAc 98 / 2) to give (2a). Yield: 27%.

[0051] -Methyl 2,3,3,5,6,6-hexamethyl-4-oxocyclohex-1-enecarboxylate (2b)

[0052] (2a) (1.0g, 4.38mmol) in THF (5ml) was slowly added to LDA (f...

Embodiment 2

[0075] Preparation of Perfuming Compositions

[0076] A perfuming composition for a body wash was prepared by mixing the following ingredients:

[0077]

[0078]

[0079] *in dipropylene glycol

[0080] 1) (-)-(8R)-8,12-epoxy-13,14,15,16-destetramethyllysium (tetranorlabdane); source: Firmenich SA, Geneva, Switzerland

[0081] 2) Tetrahydro-2-isobutyl-4-methyl-4(2H)-pyranol; source: Firmenich SA, Geneva, Switzerland

[0082] 3) Methyl cis-dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0083] 4) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone; source: International Flavors&Fragrances, USA

[0084] 5) Methyl dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0085] 6) 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol; source: Firmenich SA, Switzerland, Geneva

[0086] Adding 4500 parts by weight of 5,5,6,7,8,8-hexamethyl-3,4,5,8-tetrahydro-1(2H)-naphthone to the above composition gave the composition a strong The m...

Embodiment 3

[0089] Preparation of Perfuming Compositions

[0090] A perfuming composition for men's eau de toilette was prepared by mixing the following ingredients:

[0091]

[0092]

[0093] *in dipropylene glycol

[0094] 1) Methyl cis-dihydrojasmonate; source: Firmenich SA, Geneva, Switzerland

[0095] 2) 4 / 3-(4-Hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde; Source: International Flavors & Fragrances, USA

[0096] 3) 3,3-Dimethyl-5-(2,2,3-trimethyl-3-cyclobasten-1-yl)-4-penten-2-ol; source: Firmenich SA, Switzerland ,Geneva

[0097] The addition of 2000 parts by weight of 5,5,6,7,8,8-hexamethyl-1,4,5,8-tetrahydro-1(2H)-naphthone to the above combination rendered the composition pure The (animal-free) musk-vanilla specific (twist), boosts the aromatic notes, increases the freshness of the original composition and adds a light fruity note.

[0098] When replacing the compound of the present invention and using the same amount of prior art (6RS, 7RS)-5,5,6,7,8,8-hexam...

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Abstract

The present invention relates to compounds of Formula (I), wherein the dotted line represents a carbon-carbon single or double bond and R represents a hydrogen atom or a methyl group; which are useful perfuming ingredients to impart odor notes of the musky-earthy and woody, aromatic-fresh type.

Description

technical field [0001] The present invention relates to the field of fragrances. More specifically, the present invention relates to certain penta / hexamethyl-3,4,5,8-tetrahydro-1(2H)-naphthalenone derivatives of general formula (I) as defined below, which are useful perfuming Element. The present invention also comprises a compound 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 general formula (I) according to the invention are novel. [0003] As far as we know, the closest analogues known in fragrances and belonging to the same broad olfactory family are those described in EP1689728, which in any case have a different structure and also have a significantly different musky odor type. These prior art documents do not report or suggest any organoleptic properties of the compounds of general formula (I) discussed further below, nor do they report or suggest any...

Claims

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Application Information

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IPC IPC(8): C07C49/637C11B9/00C11D3/20
CPCC07C49/637C11B9/0053C07C2602/10
Inventor C·菲尔
Owner FIRMENICH SA
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