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Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals

An aromatic and unsubstituted technology, applied in the field of preparing perfuming compositions or changing the aroma characteristics of perfuming compositions, changing the aroma characteristics of perfuming compositions, ethers or esters of 1-substituted cycloalkanols, and being able to solve new problems. Flavors and fragrances are difficult, laborious, and materially difficult to explore to achieve novel and beneficial sensory attributes

Pending Publication Date: 2021-05-28
BASF SE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, since even small changes in chemical structure can cause large changes in sensory properties such as odor as well as taste, it is extremely difficult to target substances with specific sensory properties such as specific smells
The search for new flavors and fragrances is therefore in most cases difficult and laborious, it is not known whether a substance with the desired smell and / or taste will actually be found

Method used

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  • Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals
  • Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals
  • Ethers and esters of 1-substituted cycloalkanols for use as aroma chemicals

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0477] abbreviation:

[0478] GC: gas chromatography

[0479] RT: retention time

[0480] DMAP: 4-Dimethylaminopyridine

[0481] MTBE: methyl tert-butyl ether

[0482] analyze:

[0483] The purity of the product was determined on an area % basis by gas chromatography:

[0484] GC system: Agilent 7890B;

[0485] GC column: DB-WAX (30m (length), 0.32mm (ID), 0.25 micron (film));

[0486] Temperature program: from 85°C to 230°C at 5°C / min

[0487] pass 13 C NMR identifies the product.

[0488] 1. Preparation Example

[0489] 1.1 Preparation of 1-ethynyl-cyclohexane-1-ol

[0490] In a 5-liter autoclave, 308.5 g (5.5 mol) of sodium methoxide were suspended in 1500 ml of tetrahydrofuran and purged with nitrogen. The autoclave was pressurized at 10°C with 2 bar nitrogen and 18 bar acetylene. 5 moles of cyclohexanone were added continuously over 16 hours at 10° C. while maintaining the pressure at 20 bar. The mixture was stirred at 0 °C for an additional 5 hours befo...

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PUM

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Abstract

The present invention relates to the use of an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific ethers or esters of 1 -substituted cycloalkanols.

Description

[0001] The present invention relates to ethers or esters of 1-substituted cycloalkanols or mixtures of two or more ethers or esters of 1-substituted cycloalkanols or stereoisomers thereof or two or more stereoisomers thereof Use of mixtures of compounds as aroma chemicals; their use for modifying the aroma profile of perfuming compositions; ethers or esters containing 1-substituted cycloalkanols or two or more 1-substituted cycloalkanols Aromachemical compositions of mixtures of ethers or esters or stereoisomers thereof or mixtures of two or more stereoisomers thereof; and to processes for preparing perfuming compositions or for modifying the aroma profile of perfuming compositions. [0002] The invention further relates to ethers or esters of particular 1-substituted cycloalkanols. [0003] technical background [0004] Fragrance chemicals, especially fragrances, are of interest especially in the field of cosmetics and cleaning and laundry compositions. Fragrances of natural ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/184C07C43/188C07C69/013C07C69/14C07C69/145C07C69/24A61K8/34C11B9/00
CPCC07C43/184C07C43/188C07C69/013C07C69/14C07C69/145C07C69/24C07C2601/08C07C2601/14C11B9/0015C11B9/0019
Inventor C·斯托克M·布鲁罗伊格R·派尔泽F·加尔利希斯M·丹兹
Owner BASF SE