Capric acid derivatives and fragrance compositions

A composition and fragrance technology, applied in essential oils/fragrances, food science, fat production, etc., can solve the problem of satisfactory aroma and achieve a variety of effects

Active Publication Date: 2016-08-31
T HASEGAWA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The compound can also be purified by distillation, but the aroma may not be satisfactory

Method used

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  • Capric acid derivatives and fragrance compositions
  • Capric acid derivatives and fragrance compositions
  • Capric acid derivatives and fragrance compositions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: the synthesis of methyl 5-hydroxydecanoate

[0051] Under a nitrogen atmosphere, δ-decalactone (manufactured by Sigma-Aldrich Japan K.K., 17.0 g, 0.10 mol) and methanol (190.0 g) were put into a 500 mL four-neck flask, and sodium methoxide (Junsho Chemical Co., Ltd. Co., Ltd., 28% methanol solution, 3.3 g, 0.017 mol). After stirring overnight at room temperature, glacial acetic acid (1.0 g, 0.017 mol) was added for neutralization, and concentrated under reduced pressure. Saturated brine (100 mL) was added to the obtained residue, followed by extraction with ether (200 mL), and the obtained ether layer was washed sequentially with saturated aqueous sodium bicarbonate (100 mL) and saturated brine (100 mL). By drying over anhydrous magnesium sulfate and concentrating under reduced pressure, 5-hydroxydecanoic acid methyl ester (18.0 g) was obtained as a colorless oily crude product. The yield was 89%.

Embodiment 2

[0052] Embodiment 2: the synthesis of methyl 5-formyloxydecanoate

[0053] Methyl 5-hydroxydecanoate (7.9 g, 0.039 mol) and pyridine (manufactured by Junsei Chemical Co., Ltd., 31.6 g) obtained in Example 1 were put into a 100 mL three-necked flask, and stirred under ice water cooling at 0 A mixed solution of acetic anhydride (10.0 g, 0.098 mol) and 98% formic acid (manufactured by Junsei Chemical Co., Ltd., 4.6 g, 0.101 mol) was added dropwise at ~10°C / 30 minutes. After stirring overnight at room temperature, methanol (17.6 g, 0.55 mol) was added dropwise at 5 to 15° C. / 10 minutes under ice-cooling, and stirred at room temperature for 30 minutes. Pour into cold 10% hydrochloric acid (100mL), extract with ether (60mL×2 times), and wash the obtained ether layer with cold 10% hydrochloric acid (100mL), saturated aqueous sodium carbonate solution (100mL×2 times) and saturated saline ( 100mL) and washed in turn. After drying over anhydrous magnesium sulfate and concentrating und...

reference example 1

[0059] Reference Example 1: Synthesis of 5-acetoxydecanoic acid methyl ester

[0060] Methyl 5-hydroxydecanoate (10.1 g, 0.05 mol) and pyridine (manufactured by Junsei Chemical Co., Ltd., 40.3 g) obtained in Example 1 were put into a 100 mL three-necked flask, and stirred under ice water cooling with 5 Acetic anhydride (10.2 g, 0.10 mol) was added dropwise at ~8°C / 10 minutes. After stirring overnight at room temperature, methanol (18.0 g, 0.56 mol) was added dropwise at 5 to 15° C. / 10 minutes under ice-cooling, and stirred at room temperature for 30 minutes. Pour into cold 10% hydrochloric acid (100mL), extract with ether (60mL×2 times), and wash the obtained ether layer with cold 10% hydrochloric acid (100mL), saturated aqueous sodium carbonate solution (100mL×2 times) and saturated saline ( 100mL) and washed in turn. After drying over anhydrous magnesium sulfate and concentrating under reduced pressure, the resulting residue (12.0 g) was purified by distillation to obtain ...

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Abstract

This invention relates to alkyl 5-acyloxydecanoate having formula (1) as follows: wherein R1 denotes a hydrogen atom or an alkyl group having one to four carbon atoms, R2 denotes an alkyl group having one to four carbon atoms, with the proviso that the case where R1 is a methyl group and R2 is a methyl group or an ethyl group is excluded, which is capable of giving to food products or the like a characteristic flavor, or a sensory impression, of milk, fat or cream, and to the use of the same in flavoring compositions.

Description

technical field [0001] The present invention relates to a novel capric acid derivative useful as a fragrance compound and the like, and a fragrance composition containing the derivative as an active ingredient. Background technique [0002] In recent years, along with the diversification of consumers' hobbies, it is desired to develop various products that meet the needs of consumers. In particular, this tendency is strong in the beverage and food industry, and there is a strong demand for the development of diverse beverages and foods that cater to consumers' preferences. In response to these demands, flavors, which are one of the raw materials of food and beverages, cannot be adequately met by conventionally proposed flavor (flavor, food flavor) compounds, and development of unique aroma and flavor characteristics that did not exist before and excellent persistence Fragrance compounds are an urgent issue. [0003] Capric acid derivatives known as flavor compounds include...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/675A23L27/20A61K8/37A61Q13/00C11B9/00A21D2/14A21D13/08A23C9/152A23D7/00A23F3/16A23F5/24A23G9/04A23L9/20
CPCA23L27/206A21D2/14A23C9/152A23D7/0056A23D7/013A23D9/007A23D9/013A23F3/163A23F5/243A23F5/405A23F5/465A23G9/32A23L2/56A23L2/66A23L27/2028A61K8/37A61K2800/10A61Q19/00C07C69/34C07C69/67C11B9/0019
Inventor 小黒大地原口贤治高久宽康
Owner T HASEGAWA CO LTD
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