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Preparation method of erythro-aleuritic acid

A kind of technology of Lagaric acid and Su-style, which is applied in the field of synthesis of natural products, can solve the problems of preparation and property research of red-formed Lacaric acid, and achieve high conversion efficiency of raw materials, simple operation and stable reaction temperature Effect

Active Publication Date: 2021-02-19
THE RES INST OF RESOURCES INSECTS RIRI OF THE CHINESE ACADEMY OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no systematic literature reports on the preparation and properties of erythro-lacaricic acid at home and abroad

Method used

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  • Preparation method of erythro-aleuritic acid
  • Preparation method of erythro-aleuritic acid
  • Preparation method of erythro-aleuritic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1 prepares erythro-type lacaric acid

[0060] 1. The first reflux treatment

[0061] 30.4g threo type laccarnation acid (A, 0.1 mole) and 300ml concentration are 36.5% hydrochloric acid (3.537 mole) to be placed in the round bottom flask with reflux condenser, add catalyst ST (ZnCl 2 , 0.002 moles) and mix well; then place the flask in an oil bath to heat, feed condensed water, and under stirring, carry out the first heating-reflux treatment; wherein: the molar ratio of threo-type largaeic acid to HCl It is 1:35.37 (usually 1:15-36); the molar ratio of threo-style lacaric acid to catalyst ST is 1:0.02 (usually 1:0.001-0.070); the temperature of the first heating-reflux treatment is (100±1)°C (usually the temperature range for the first heating-reflux treatment is (90-100)±1)°C;

[0062] After the first heating-reflux treatment for 10h (usually 5-12h), cool to room temperature, suction filter, and wash the filter residue with deionized water until there is n...

Embodiment 2

[0087] 1. The first reflux treatment

[0088] In addition to the molar ratio of threo-style lactoic acid to HCl is 1:15 (usually 1:15-36); the molar ratio of threo-style lactoic acid to catalyst ST is 1:0.07; the first heating-reflux treatment The temperature is (90±1)°C (the temperature range of the first heating-reflux treatment is usually (90-100)±1)°C); except for the first heating-reflux treatment for 12h, the rest are the same as in Example 1. 1 is the same. The preparation yielded 22.6 g of intermediate IM.

[0089] 2. The second heating - reflux treatment

[0090] Except that the mass percent concentration of the NaOH aqueous solution is 5%; the temperature of the second heating-reflux treatment is (90±1)° C., the rest is the same as step 2 of Example 1.

[0091] 3. Acid analysis treatment

[0092] Except heating for the second time-reflux treatment 36h (being generally 25-36h); The mass percent concentration of the dilute hydrochloric acid that adds in the reactio...

Embodiment 3

[0094] 1. The first reflux treatment

[0095] Except that the molar ratio of threo-style lacaric acid to HCl is 1:30 (usually 1:15-36); the molar ratio of threo-style lactalic acid to catalyst ST is 1:0.001; the first heating-reflux treatment The temperature is (100±1)°C (the temperature range of the first heating-reflux treatment is usually (90-100)±1)°C); except for the first heating-reflux treatment for 5h, the rest are the same as in Example 1. 1 is the same. The preparation yielded 26.5 g of intermediate IM.

[0096] 2. The second heating - reflux treatment

[0097] Except that the mass percent concentration of the NaOH aqueous solution is 8%; the temperature of the first heating-reflux treatment is (100±1)° C., the rest are the same as step 2 of Example 1.

[0098] 3. Acid analysis treatment

[0099] Except heating for the second time-reflux treatment 25h (being generally 25-36h); The mass percent concentration of the dilute hydrochloric acid that adds in the reactio...

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Abstract

The invention provides a preparation method of erythro-aleuritic acid. The preparation method comprises the following steps: taking threo-aleuritic acid as a raw material, carrying out twice heating reflux and acid precipitation treatment to obtain erythro-aleuritic acid. Erythro-aleuritic acid is prepared through configuration conversion of threo-aleuritic acid, and a product is analyzed and confirmed by adopting characterization means such as FTIR, mass spectrum, nuclear magnetism, TG, DSC, XRD, chiral resolution, optical activity and the like. FTIR, mass spectrum, and nuclear magnetism showthat the structure of the product is consistent with that of threo-aleuritic acid; XRD, DSC and TG results show that the crystal form of threo-aleuritic acid is the same as that of the product, but the melting point of the product is higher, and the cell size is smaller; chiral resolution shows that the product is an optical isomer of aleuritic acid, that is, the product is determined to be erythro-aleuritic acid. The disclosed method can be used for effectively converting threo-aleuritic acid into erythro-aleuritic acid, and is high in conversion efficiency, high in yield of erythro-aleuritic acid and high in purity of erythro-aleuritic acid.

Description

technical field [0001] The invention relates to a preparation method of a natural product, in particular to a preparation method of lac jatrophic acid and erythroic lac jatrophic acid prepared by the method, and belongs to the technical field of synthesis and application of natural products. Background technique [0002] Lac garlic acid, also known as papiacarpic acid, is a kind of 9,10,16-trihydroxyhexadecanoic acid extracted from lac resin, and its appearance is white crystal. Lac jaulic acid is mainly prepared from lac resin through saponification, salting out, decolorization, recrystallization and other processes. Lacic acid has a wide range of uses, and is often used as a precursor for the synthesis of prostaglandins, cyclic ureas, insect pheromones, etc., and as a raw material for macrocyclic musk compounds in the perfume industry, and has a good application prospect. [0003] For a long time, the researches on largaric acid have focused on the preparation and detecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/353C07C59/105
CPCC07C51/353C07B2200/09C07B2200/13C07C59/105
Inventor 李坤唐保山张弘石小娟张雯雯马金菊刘兰香徐涓
Owner THE RES INST OF RESOURCES INSECTS RIRI OF THE CHINESE ACADEMY OF FORESTRY