Compound, salt of compound, external agent for skin, cosmetic, and food additive

一种化合物、通式的技术，应用在化妆品、化妆品配制品、护理皮肤的制剂等方向，能够解决效果不充分等问题，达到吸收性高的效果

Active Publication Date: 2017-08-29
RESONAC CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the conventional external preparations containing pantothenic acid or the like have a problem that the effect of improving symptoms is not sufficient.

Method used

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  • Compound, salt of compound, external agent for skin, cosmetic, and food additive
  • Compound, salt of compound, external agent for skin, cosmetic, and food additive
  • Compound, salt of compound, external agent for skin, cosmetic, and food additive

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0206] According to the following steps, the compound shown in the following formula (1)-301 (in the general formula (1), R 1 is a hydrogen atom, R 2 The compound which is a linear hexadecanoyl group is hereinafter abbreviated as "compound (1)-301").

[0207]

[0208] Calcium pantothenate (manufactured by Tokyo Chemical Industry Co., Ltd., 19.1 g, 40.1 mmol), pyridine (manufactured by Wako Pure Chemical Industries, Ltd., 19.0 g, 240 mmol) and 4-dimethylaminopyridine (DMAP) (manufactured by Wako Pure Chemical Industries, Ltd., 0.49 g, 4.0 mmol) was added to tetrahydrofuran (THF) (manufactured by Wako Pure Chemical Industries, Ltd., 560 mL) and stirred, and palmitoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd., 22.6 g, 82.2 mmol) was added dropwise at room temperature (25° C.) over 3 hours, and further stirred at room temperature for 3.5 hours after the dropwise addition was completed. At this time, a part of the reaction liquid was sampled, analyzed by HPLC...

Embodiment 2

[0216] According to the following steps, the compound shown in the following formula (1)-302 (in the general formula (1), R 1 is a hydrogen atom, R 2 A branched 2-hexyldecanoyl compound is hereinafter abbreviated as "compound (1)-302").

[0217]

[0218] As an acylating agent, it reacted similarly to Example 1 except having used 2-hexyldecanoyl chloride (made by Nippon Seika Co., Ltd.) instead of palmitoyl chloride, and having made reaction temperature 50 degreeC instead of room temperature. A part of the reaction solution was sampled, analyzed by HPLC, and quantified. As a result, the yield of the target compound (1)-302 was 13.4%. Thereafter, post-treatment of the reaction solution, extraction of the crude product, and purification by column chromatography were carried out in the same manner as in Example 1, whereby the target compound (1)-302 was obtained as a pale yellow oil. (IUPAC name: 3-[N-(4-(2-hexyldecanoyl)oxy-3,3-dimethyl-2-hydroxybutyryl)amino]propanoic acid)...

reference example 1

[0224] According to the following procedure, a compound represented by the following formula (9)-101 (hereinafter, abbreviated as "compound (9)-101") was produced.

[0225]

[0226] As the acylating agent, instead of palmitoyl chloride, decanoyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.) was used, and the reaction was carried out in the same manner as in Example 1. A part of the reaction solution was sampled, analyzed by HPLC, and quantified. As a result, the yield of (9)-101, which is the target substance, was 24.4%. Hereinafter, post-treatment of the reaction solution, extraction of the crude product, and purification by column chromatography were carried out in the same manner as in Example 1 to obtain the target compound (9)-101 (IUPAC Name: 3-[N-(4-decanoyloxy-3,3-dimethyl-2-hydroxybutyryl)amino]propanoic acid) (yield 3.41g (9.14mmol), isolated yield 11.4%) .

[0227] The obtained product is compound (9)-101 through 1 H-NMR and 13 It was confirmed...

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Abstract

The present invention provides a compound represented by general formula (1), or a salt thereof (where R1 and R2 are each independently a hydrogen atom or a linear-chain or branched-chain C11-30 acyl group, a hydrocarbon group bonded to a carbonyl carbon of the acyl group is a saturated or unsaturated hydrocarbon group, and at least one of R1 and R2 is the acyl group.)

Description

technical field [0001] The present invention relates to a compound, a salt of the compound, an external preparation for skin, a cosmetic and a food additive. [0002] This application claims priority based on Japanese Patent Application No. 2015-007865 for which it applied in Japan on January 19, 2015, and uses the content here. Background technique [0003] Pantothenic acid, also known as vitamin B5, is a constituent factor of coenzyme A that is indispensable for the metabolism of carbohydrates, lipids, and proteins and the production of energy, and is also involved in the synthesis of cholesterol, hormones, and immune antibodies. [0004] Thus, pantothenic acid is an important compound involved in various functions in a living body, and if they are deficient, various symptoms appear in the living body. For example, due to the lack of pantothenic acid, if the secretion of sebum is disturbed, the metabolism of the skin cannot be performed normally, causing dermatitis, acne,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/12A23L33/15A61K8/44A61K31/197A61P3/02A61P17/00A61Q19/00
CPCA61K8/44A61Q19/00A23L33/15C07C235/12A61Q19/008A61K31/197A23V2002/00A61K8/673A61K2800/10
Inventor 橘彻新林良太柳生大辅
Owner RESONAC CORPORATION
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