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Method for splitting aleutric acid enantiomer

A technology of laccarlelic acid and enantiomers, which is applied in the resolution of racemate compounds and the field of laccarlenic acid resolution, can solve the problems of in-depth research, achieve good repeatability, fast peak time, short time effect

Inactive Publication Date: 2019-10-18
THE RES INST OF RESOURCES INSECTS RIRI OF THE CHINESE ACADEMY OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, do all four enantiomers actually exist? In fact, the view that only the Su-type configuration exists in lac has been mentioned in relevant research reports, but the research has not been in-depth, and there is no complete chain of evidence to confirm it

Method used

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  • Method for splitting aleutric acid enantiomer
  • Method for splitting aleutric acid enantiomer
  • Method for splitting aleutric acid enantiomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1 Establishment of enantiomer resolution method of laccarlenic acid

[0055] 1-1) Selection of mobile phase composition

[0056] Accurately weigh 100 mg of a sample of jatrophic acid, dissolve it in methanol, and set the volume to 100 mL to prepare a solution of lac jatrophic acid (i.e., a mixture of lac jatrophic acid) with a concentration of 1 mg / mL, and then dissolve it with 0.45 μm cellulose acetate After filtering through the needle filter membrane, use a micro-sampling needle to draw 5 μL of the sample solution for injection, and inject it into a high-performance liquid chromatograph (Agilent 1200 high-performance liquid chromatography: Agilent Technologies Co., Ltd., USA) for separation, wherein: methanol (C) , acetonitrile (B), 0.1% formic acid aqueous solution (A) are mobile phase components, and mobile phase consists of 0.1% formic acid aqueous solution water: methanol=(20-50):(50-80) (V / V), 0.1% Formic acid aqueous solution: acetonitrile = (20-50)...

Embodiment 2

[0092] Embodiment 2 The content of the enantiomer of laccarpus acid and the determination of ee value

[0093] Prepare 0.5 mg / mL of the lactoic acid helicoid solution, according to the resolution conditions determined in the steps 1-3) of Example 1, split, and adopt the peak area normalization method to measure the prepared lactoic acid enantiomer Enantiomer content, and calculate the enantiomeric excess value (ee value). The calculation method of ee value is as formula (Ⅰ):

[0094]

[0095] In the formula, [a]: the percentage content / % of the first enantiomer; [b]: the percentage content / % of the second enantiomer. The measurement results are shown in Table 5.

[0096] Table 5 Determination table of two enantiomer content and ee value of laccarnation acid

[0097]

[0098] As can be seen from Table 5, under the above-mentioned optimal conditions determined, when the preparation of Lacic acid was carried out to measure the enantiomer content with 0.5mg / mL concentrati...

Embodiment 3

[0099] The infrared spectrum (FTIR) comparative analysis of the laccarlenic acid before and after the resolution of embodiment 3

[0100] Get Lacic acid (Ⅲ) before the resolution and the enantiomer (i, ii) after the resolution, and carry out the infrared absorption spectrum test according to the following conditions respectively: the tabletting substrate is potassium bromide, the pressure is 10MPa, and the infrared scanning wavenumber The range is 4000~400cm -1 , resolution 4cm -1 , accumulatively scanning 32 times.

[0101] Measurement results such as Image 6 shown by Image 6 It can be seen that the infrared absorption characteristics of the heteromorph (Ⅲ) and the enantiomer i and ii samples of lac jaloic acid are basically the same, and it can be seen that the prepared and resolved lac jatrophic acid i and ii samples are consistent with the structure of lac jatrophic acid sex. The main characteristic absorption peaks are assigned as follows: at 3306cm -1 It is the s...

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Abstract

The invention discloses a method for splitting aleutric acid enantiomer. According to the method, after aleutric acid is prepared into a solution, HPLC separation is performed. Therefore, the enantiomer of the aleutric acid can be split rapidly and the prepared product has high purity. The preparation method is simple and is suitable for industrial production. Moreover, with the HPLC-ELSD method,the split and detection conditions of the aleutric acid stereisomer are established to provide a reference base for the split detection of optically pure aleutric acid and chromatographic preparation.

Description

technical field [0001] The invention relates to a resolution method of a racemate compound, in particular to a resolution method of lacgaric acid, and belongs to the technical field of resolution of chemical optical isomers. Background technique [0002] Lac is a natural resin mixture secreted by lac insects, mainly composed of lac resin, lac wax and lac pigment. Lac resin is a lactone and lactide composed of hydroxy fatty acids represented by lacaric acid and sesquiterpene acids represented by chitosinic acid. Shellac resin is widely used in food, medicine, military industry, coatings and other industries due to its excellent film-forming properties, adhesion, salt spray resistance, and water resistance. After destroying the lactone and lactide bonds in the lac resin, a series of extraction and purification processes are performed to obtain the lac jatrophic acid. [0003] Lacic acid, namely 9,10,16-trihydroxyhexadecanoic acid, chemical formula C 16 h 32 o 5 , is a whi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N30/06G01N30/74
CPCG01N30/06G01N30/74
Inventor 李坤张弘涂行浩张雯雯李凯郑华刘兰香
Owner THE RES INST OF RESOURCES INSECTS RIRI OF THE CHINESE ACADEMY OF FORESTRY
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