Unsaturated macrocyclic epoxides as perfuming ingredients
A technology for perfuming ingredients and compounds, which is applied in softening compositions, formulations of perfume preparations, cosmetics, etc., and can solve problems such as sensory properties that are not implied
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Embodiment 1
[0074] The preparation of formula (I) compound
[0075] To a mixture of sodium carbonate (160 g, 1.23 mol, 2.9 equiv) in toluene (1000 mL) was added cyclododeca-1,5,9-triene (II-a) (500 g, 3.1 mol, 1 equiv). The mixture was cooled to 0 °C and to it was added peracetic acid (1000 mL, 3.9 mol, 1 equiv) dropwise over a period of 5 minutes. The reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction mixture was then cooled to 0 °C and poured into NaHSO 3 in aqueous solution. Use NaHCO 3 The organic layer was washed with aqueous solution, then water, and finally brine. The combined organic extracts were dried using sodium sulfate, and the solvent was evaporated. The residue was purified by distillation under reduced pressure (0.07 mbar, 110° C.) to provide a mixture of stereoisomers of 13-oxabicyclo[10.1.0]trideca-4,8-diene. Based on analysis, the mixture of stereoisomers consisted of 80% (1RS,4E,8Z,12RS)-13-oxabicyclo[10.1.0]trideca-4,8-d...
Embodiment 2
[0077] Preparation of Perfuming Compositions
[0078] A perfuming composition for a masculine cologne is prepared by mixing the following ingredients:
[0079]
[0080]
[0081] *in dipropylene glycol
[0082] **in isopropyl myristate
[0083] 1) 16-hexadecanolide a)
[0084] 2)(-)-(8R)-8,12-epoxy-13,14,15,16-destetramethylresbutane a)
[0085] 3) Allyl ionone b)
[0086] 4) 7-Methyl-2H,4H-1,5-benzodioxane-3-one a)
[0087] 5) 1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4-indanone c)
[0088] 6) Pentadecalactone a)
[0089] 7) Pentadecenolactone a)
[0090] 8) Methyl cis dihydrojasmonate a)
[0091] 9) (1S,1'R)-2-[1-(3',3'-dimethyl-1'-cyclohexyl)ethoxy]-2-methylpropyl propionate a)
[0092] 10) 3-(3,3 / 1,1-Dimethyl-5-indanyl)propionaldehyde a)
[0093] 11) 1-(Octahydro-2,3,8,8-tetramethyl-2-naphthyl)-1-ethanone c)
[0094] 12) 4 / 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde c)
[0095] 13) 3-Methyl-5-cyclopentadecen-1-one a)
[0096...
Embodiment 3
[0106] Preparation of Perfuming Compositions
[0107] A detergent perfuming composition is prepared by mixing the following ingredients:
[0108]
[0109]
[0110] *in dipropylene glycol
[0111] **in isopropyl myristate
[0112] 1) The terpene part of patchouli oil, obtained by the fermentation of sugar a)
[0113] 2) 1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta-g-2-benzopyrene c)
[0114] 3) Pentadecenolactone a)
[0115] 4) cis methyl dihydrojasmonate a)
[0116] 5) 1-Styryl Acetate a)
[0117] 6) 3-(4-tert-butylphenyl)-2-methylpropanal b)
[0118] 7) Ethyl 4-(1,1-dimethylethyl)-1-cyclohexyl ester a)
[0119] 8) 3-Methyl-5-cyclopentadecen-1-one a)
[0120]9) (6R)-perhydro-3,6-dimethyl-benzo[b]furan-2-one a)
[0121] 10) Compound spice base a)
[0122] a) Source: Firmenich SA, Geneva, Switzerland
[0123] b) Source: Givaudan-Roure SA, Vernier, Switzerland
[0124] c) Source: International Flavors & Fragrances, USA
[0125] Adding 300...
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