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Novel ambergris and/or indole-like compositions of odoriferous substances

A fragrance and composition technology, applied in the directions of essential oils/fragrances, detergent composition fragrances, formulations of fragrance preparations, etc., can solve the problem of difficulty in expressing the odor of ambergris, and achieve improved olfactory impression, high odor intensity Effect

Pending Publication Date: 2020-02-18
SYMRISE GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

A disadvantage of many ambergris fragrances is that their olfactory impression is only perceived gradually, making it difficult to express ambergris in the top notes of a perfume

Method used

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  • Novel ambergris and/or indole-like compositions of odoriferous substances
  • Novel ambergris and/or indole-like compositions of odoriferous substances
  • Novel ambergris and/or indole-like compositions of odoriferous substances

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Example 1: Synthesis of 4-tert-butyl-1-methyl-cyclohexanol (Grignard reaction)

[0125] 200 ml of methylmagnesium chloride solution (3M in THF) and 100 ml of THF were placed in a stirrer with a magnetic stirrer under a nitrogen atmosphere. Subsequently, 83.2 g (0.54 mol) of 4-tert-butylcyclohexanone dissolved in 200 ml of THF was added dropwise at 20° C. to 25° C. within 1 hour to 2 hours. The mixture was further stirred at room temperature for 2 to 3 hours. The deposit was poured into a cold saturated ammonium chloride solution at 0° C. to 5° C., then extracted by shaking with MTBE, and the organic phase was washed with soda solution and then with NaCl solution. After evaporation, 84.6 g of crude product were obtained.

[0126] The material is distilled in a small column.

[0127] Yield: 77.8 g (84.7% of theory)

Embodiment 2

[0128] Embodiment 2: the synthesis (etherification) of 4-tert-butyl-1-methyl-cyclohexanol methyl ether

[0129] In a stirrer with a magnetic stirrer, a solution consisting of 42.5 g (0.25 mol) of 4-tert-butyl-1-methyl-cyclohexanol in 100 ml of anhydrous THF at 20 °C was brought under nitrogen atmosphere 0.3 mol of 60% sodium hydride in anhydrous THF was added dropwise. It was then stirred for a further 5 hours at room temperature. Subsequently, 42.6 g (0.3 mol) of methyl iodide in 100 ml of anhydrous THF were added dropwise at room temperature within 30 minutes. It was then stirred for a further 2 hours at room temperature. The reaction mixture was carefully mixed with 250 ml of ice-cold water under cooling, and after separation of the aqueous phase, it was washed neutrally again twice with 50 ml of saturated saline solution each. After distilling off the solvent, the residue was distilled in a small column.

[0130] Yield: 28.8 g (62.8% of theory)

[0131] The same auxil...

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Abstract

The present invention relates primarily to the use of one or more compounds of formula (I) as perfume, wherein R represents methyl or ethyl and R1 H represents methyl or ethyl. The invention also relates to novel odoriferous substances comprising one or more compounds of formula (I) as described herein, to the use of said odoriferous substances, perfumed articles comprising said odoriferous substances and to diverse methods for perfuming said article or for imparting, modifying and / or intensifying certain fragrance notes.

Description

technical field [0001] The present invention primarily relates to the use of one or more compounds of the formula (I) as described herein as a fragrance. The present invention also relates to novel fragrance compositions comprising one or more compounds of formula (I) as described herein, the use of said fragrance composition, the perfuming of said fragrance composition Articles, and methods for perfuming said articles or for imparting, altering and / or intensifying particular notes. [0002] Further aspects and preferred embodiments of the invention emerge from the ensuing embodiments, the appended examples and especially the appended claims. Background technique [0003] In the perfumery industry a large variety of compounds are known for imparting fragrance. However, there is always a need for new types of advantageous compounds which, in addition to their positive and original olfactory properties, also have additional positive secondary properties. [0004] When searc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11B9/00A61K8/34A61Q15/00C11D3/50
CPCA61K8/34C11B9/0034C11D3/50A61K8/33A61Q13/00
Inventor 贝恩德·霍尔舍约翰内斯·潘滕
Owner SYMRISE GMBH & CO KG
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