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Hydroxylated fatty acid homopolymer and production method thereof

一种氢氧化脂肪酸、制造方法的技术，应用在氢氧化脂肪酸的均聚物领域，能够解决比例变少、未有所报告等问题

Active Publication Date: 2020-06-12
KYOTO UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, triglycerides and alkyl esterifications require reactions with glycerin and alcohols in addition to hydrogenated fatty acids. Therefore, the proportion of structural units in the molecule derived from HYA is reduced, and it is not possible to provide a high content of HYA. Shape
[0005] On the other hand, no derivatives of hydrogenated fatty acids that can solve the above-mentioned problems have been reported so far.

Method used

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  • Hydroxylated fatty acid homopolymer and production method thereof
  • Hydroxylated fatty acid homopolymer and production method thereof
  • Hydroxylated fatty acid homopolymer and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0280]

[0281] 0.3 mL of milliQ water was added to 184 mg of 10-hydroxy-cis-12-octadecenoic acid, and ultrasonic treatment was performed for 20 seconds. 11 mg of lipase AY "Amano" 30SD was added, stirred at 37° C. and 130 rpm for 24 hours, and reacted. Utilize the Bligh-Dyer method to extract the liquid after the reaction, and utilize silica gel chromatography (developing solvent hexane:diethyl ether:acetic acid=40:60:1) to carry out separation and purification, obtain the 2 polymer (9.4mg) of HYA , a 3-mer of HYA (4.7 mg) and a 4-mer of HYA (7.9 mg).

[0282] 2-mer of HYA

[0283] Rf value = 0.30 by silica gel chromatography (developing solvent: hexane: diethyl ether: acetic acid = 40:60:1).

[0284]

[0285] 3-mer of HYA

[0286] The Rf value based on silica gel chromatography (developing solvent: hexane: diethyl ether: acetic acid = 40:60:1) = 0.38.

[0287]

[0288] 4-mer of HYA

[0289] The Rf value by silica gel chromatography (developing solvent: hexane: d...

Embodiment 2

[0293]

[0294] 0.3 mL of milliQ water was added to 184 mg of 10-hydroxy-cis-12-octadecenoic acid, and ultrasonic treatment was performed for 20 seconds. Then, 11 mg of lipase AY "Amano" 30SD was added, and it stirred and reacted at 37 degreeC and 130 rpm for 24 hours. Only oil and fat components were extracted from the reacted liquid by the Bligh-Dyer method, and the liquid concentrated by a rotary evaporator was subjected to thin-layer chromatography (TLC Silica gel 60 F254; developing solvent: hexane: diethyl ether: Acetic acid=40:60:1). The results of thin layer chromatography (365nm ultraviolet irradiation) are shown in figure 1 .

[0295] according to figure 1 It is possible to confirm the point where HYA aggregated. From the number of points, it was confirmed that HYA formed 2-10 polymers.

[0296] The Rf value of each point is shown below.

[0297] 2-mer of HYA: 0.30

[0298] 3-mer of HYA: 0.38

[0299] 4-mer of HYA: 0.42

[0300] 5-mer of HYA: 0.46

[0301...

Embodiment 3

[0307]

[0308] The oxidation stability of the reaction extract (homopolymer mixture) obtained in Example 1 was compared with that of HYA. Oxidation reactions decompose NAD in the presence of fatty acid hydroxide dehydrogenase (CLA-DH) ＋ Implemented as an electron acceptor (S. Kishino et al., Polyunsaturated fatty acid saturation by gut lactic acid bacteria affecting host lipid composition. Proc. Natl. Acad. Sci. USA, 110(44), 17808-17813, 2013).

[0309] The reaction solution (3 mL) contained 150 μL of a cell-free extract of Escherichia coli expressing CLA-DH as a hydrogenated fatty acid dehydrogenase (from 50 mg of E. coli wet cells), 4 mM NAD ＋ , 150 μL of ethanol and 0.48 mM (0.143 mg / mL) of HYA as a substrate or an equivalent (0.143 mg / mL) of a homopolymer mixture, the reaction is initiated by the addition of hydrogenated fatty acid dehydrogenase and carried out at 37 °C About 6 minutes. It should be noted that, as a control, no matrix was added. During the oxidation...

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Abstract

Provided are a hydroxylated fatty acid derivative, which contains a large amount of a hydroxylated fatty acid and is easy to intake and handle, and a production method of the same. Also provided is aproduction method of a hydroxylated fatty acid homopolymer, said method comprising polymerizing a hydroxylated fatty acid using an enzyme. The hydroxylated fatty acid homopolymer is stabilized. Also provided is a valuable novel hydroxylated fatty acid homopolymer which is obtained by the aforesaid production method.

Description

technical field [0001] The present invention relates to a novel homopolymer of fatty acid hydroxide and a method for producing the same. Hydroxylated fatty acids are fatty acids having at least one hydroxyl group. In the production method of the present invention, the formation of intramolecular lactones due to intramolecular dehydration is suppressed by an enzyme, and the polymerization reaction of the hydrogenated fatty acid is selectively performed to obtain a homopolymer of the hydrogenated fatty acid. The present invention also provides novel homopolymers of hydrogenated fatty acids. The homopolymer of the hydrogenated fatty acid can be flexibly used as a raw material for medicine, food and chemicals. Background technique [0002] In recent years, the physiological functions of rare fatty acids that exist only in low proportions in living bodies have attracted attention. For example, it has been reported that conjugated fatty acids such as conjugated linoleic acid (N...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/62
CPCC12P7/62C12P7/64C12P7/625C12P7/6436C07C69/732
Inventor 小川顺岸野重信北尾浩平
Owner KYOTO UNIV
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