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Derivatives of 2,2,6-trimethylcyclohexane-carboxylate

A kind of technology of C2-C8, alkynyl group, is used in the composition field that comprises this kind of compound

Inactive Publication Date: 2016-03-23
TAKASAGO INTERNATIONAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is troublesome to replace the α,β-unsaturated ketone group of Damascone with an ester, anhydride or acyl carbonate group

Method used

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  • Derivatives of 2,2,6-trimethylcyclohexane-carboxylate
  • Derivatives of 2,2,6-trimethylcyclohexane-carboxylate
  • Derivatives of 2,2,6-trimethylcyclohexane-carboxylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0071] Example 1a: (1R,6S)-2,2,6-trimethylcyclohexanecarbonyl chloride ("acidified chloride intermediate Synthesis of (1R,6S)-isomers"):

[0072]

[0073] Thionyl chloride (1.2 equiv) was added dropwise to (1R,6S)-2,2,6-trimethylcyclohexanecarboxylic acid (1 equiv) in dichloromethane (200 mL) at 0 °C over 15 minutes cold solution. After the addition, the reaction mixture was warmed to room temperature and then heated to 50 °C for 1.5 hours. The mixture was cooled to room temperature and concentrated under reduced vacuum. The ingredients were immediately carried on to the next step.

Embodiment 1b

[0074] Example 1b: (1S,6R)-2,2,6-trimethylcyclohexanecarbonyl chloride ("acidified chloride intermediate Synthesis of (1S,6R)-isomers"):

[0075]

[0076] Thionyl chloride (1.2 equiv) was added dropwise to (1R,6S)-2,2,6-trimethylcyclohexanecarboxylic acid (1 equiv) in dichloromethane (200 mL) at 0 °C over 15 minutes cold solution. After the addition, the reaction mixture was warmed to room temperature and then heated to 50 °C for 1.5 hours. The mixture was cooled to room temperature and concentrated under reduced vacuum. The ingredients were immediately carried on to the next step.

Embodiment 2

[0077] Example 2: Synthesis of (1R,6S)-allyl-2,2,6-trimethylcyclohexanecarboxylate:

[0078]

[0079] Allyl chloride (10.5 equiv; used as solvent) was added dropwise over 20 minutes to the cold flask containing the (1R,6S)-isomer of the acidified chloride intermediate at 0°C. After the addition, the mixture was heated to 75° C. and left overnight (GC showed ~98% purity of the original reaction). The material was diluted with ethyl acetate and washed with 5% Na 2 CO 3 (2×) and water (2×). The aqueous layer was back extracted with ethyl acetate (1x). Combine organics with MgSO 4 Dry, filter and concentrate under reduced pressure. The starting material was purified (yield 67.9%) via fractional distillation (water bath = 70-71 °C, bulb temperature = 56-60 °C, vacuum pressure = 0.18-0.9 Torr). 1 HNMR (400MHz, CDCl 3 ) δppm 0.88 (m, 10H) 1.15 (m, 1H) 1.45 (m, 3H) 1.70 (dd, 1H) 1.83 (m, 2H) 4.55 (m, 2H) 5.21 (d, 1H) 5.32 (m, 1H) ) 5.91 (qd, 1H). 13 CNMR (101MHz, CDCl 3...

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Abstract

The present disclosure provides compounds that are derivatives of 2,2,6-trimethylcycIohexanecarboxylate. The disclosed compounds have useful flavor and fragrance characteristics. The present disclosure also provides flavor and fragrance compositions.

Description

[0001] priority statement [0002] This application claims priority under 35 U.S.C. §119 to U.S. Provisional Application No. 61 / 856,794, filed July 22, 2013, the entire contents of which are incorporated herein by reference. technical field [0003] The subject matter of the present disclosure relates to compounds having uses in the field of fragrances and flavors, as well as compositions comprising such compounds. Background technique [0004] There is continuing interest in the synthesis of aroma and flavor compounds and their use in consumer products. In particular there is a need for compounds having odorant properties similar to damascones. Damascenone (alpha, beta, gamma, and delta isomers) is an important odorant in the aroma and flavor industry, imparting highly dispersed distinctive fruity, green and floral notes. Damascone structurally contains an α,β-unsaturated ketone group and has therefore been labeled as a skin sensitizer. The use of Damascone in fragrance ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K8/18
CPCA23L27/203C07B2200/07C07C69/75C07C323/12C07C2601/02C07C2601/08C07C2601/14C11B9/0034A23G3/36A23L2/56A23V2002/00A61K8/37A61Q13/00C07C69/007C11D3/2093C11D3/50
Inventor T·S·丹尼尔斯M·布兰迪诺M·E·兰金
Owner TAKASAGO INTERNATIONAL CORPORATION