Method for synthesizing crocin glucoside

A technology of glucoside and synthesis method, which is applied in the field of synthesis of saffron glucoside, and can solve the problems such as high price of saffron glucoside

Inactive Publication Date: 2009-08-26
SICHUAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0067] In addition, the price of saffron glucoside is expensive, and the current price of commercially available saffron plants is: 5000-12000 yuan/kg (RMB), and the content of saffron glucoside in saffron plants is 3/10,000 To four, synthetic saffron glucoside has higher economi

Method used

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  • Method for synthesizing crocin glucoside
  • Method for synthesizing crocin glucoside
  • Method for synthesizing crocin glucoside

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Example 1 Synthesis of 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde (Compound II)

[0095] 2,7-Dimethyl-2,4,6-octatriene-1,8-dialdehyde (Compound II) has a very important position in the synthesis of conjugated polyene compounds. Through this compound, many can be synthesized Carotenoids (such as vitamin A, etc.) compounds [29-31] . In the synthesis of conjugated polyene compounds, Wittig synthesis method is one of the most important synthetic methods, and many conjugated polyene compounds are synthesized by this method [32-35] .

[0096] In the existing literature, 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde (the synthesis of compound II starts with 1,4-butadiene or furan) The product was carried out through a four-step reaction such as Wittig, but the product obtained by the Wittig synthesis method is not easy to purify in the post-treatment and the overall yield is not high [36-38] . The product obtained by the Wittig-Horner synthesis method is easily soluble in water a...

Embodiment 2

[0146] Example 2 Synthesis of Methyl E-2-methyl-4-bromo-2-butenoate

[0147] In the existing synthetic methods [39] , The synthesis of E-2-methyl-4-halo-2-butenoate is based on α-vinyl propionate as a raw material, through halogen addition, 3,4-dihalopropionate is formed, and then removed Remove one molecule of hydrogen halide to form E-2-methyl-4-halo-2-butenoate. The reaction process is:

[0148]

[0149] There is no report on the synthesis of E-2-methyl-4-bromo-2-butenoic acid methyl ester from E-2-methyl-2-butenoic acid in the existing literature. Since E-2-methyl-2-butenoic acid is a C5 type compound, which meets the design requirements, using this compound as a raw material, first synthesize E-2-methyl-4-bromo-2-butenoic acid, and then synthesize E Methyl-2-methyl-4-bromo-2-butenoate. The synthetic route is:

[0150]

[0151] 1. Experimental part

[0152] 1.1 Instruments and reagents

[0153] 1.1.1 Instrument

[0154] Varian ANOVA-400 nuclear magnetic resonance instrumen...

Embodiment 3

[0187] Example 3 Synthesis of Dimethyl Crocetin (Compound IV)

[0188] Dimethyl Crocetin is C 20 The skeleton structure of crocetin, because dimethyl crocetin contains 7 double bonds, is a polyene compound. Based on reference to other documents [43-45] , The synthesis experiment is planned to use 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde as C 10 Compound, E-2-methyl-4-bromo-2-butenoic acid methyl ester is C 5 The compound, using the reaction principle of Wittig-Horner, was synthesized crocetin dimethyl ester. The experimental design scheme is:

[0189]

[0190] 1. Experimental part

[0191] 1.1 Apparatus and reagents

[0192] All instruments are the same as in the second part.

[0193] 1.2 Synthesis experiment of E-2-methyl-2-butenoic acid methyl ester-4-phosphonic acid diethyl ester (Compound III)

[0194] The reaction equation for this step is as follows

[0195]

[0196] In a three-necked flask equipped with a dropping funnel, a vacuum distillation device and a thermomet...

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Abstract

The invention provides a method for synthesizing crocin glucoside, which comprises the following steps: a, synthesizing a C10 compound, namely 2,7-dimethyl-2,4,6-octatriene-1,8-dial (compound II); b, synthesizing a C5 compound, namely E-2-methyl-4-bromo-2- methyl crotonate; c, synthesizing crocetin dimethyl ester by taking the two compounds as raw materials; d, performing hydrolysis reaction on the crocetin dimethyl ester to obtain crocetin; and e, reacting the crocetin and 1,1'-carbonylbis-1h-imidazo to synthesize crocetin imidazole and further synthesize the crocin glucoside. The synthesizing process has the advantages in aspects of operation simplification and yield, and has high synthetic impurity, high yield, cost saving and strong industrial applicability.

Description

Technical field [0001] The invention relates to a method for synthesizing saffron glucoside and belongs to the field of medicine. Background technique [0002] Saffron, also known as saffron or saffron (Saffron, Crocus, status L), belongs to the Iridaceae plant, and mainly refers to the upper part and stigma of saffron style. Because the aqueous solution of saffron has a bright yellow color and fragrance, it is a very expensive spice. It is often used as a high-end food additive and food coloring. It can also be used as a high-end dye for silk, cotton and wool products. In the Chinese Pharmacopoeia, saffron can promote blood circulation, remove blood stasis, cool blood and detoxify, relieve depression and soothe the nerves, and is used for the treatment of amenorrhea, postpartum stasis, dampness, depression, and palpitations. Modern medical research has found that saffron has many effects in treating cardiovascular diseases and preventing atherogenesis, treating chronic viral hep...

Claims

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Application Information

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IPC IPC(8): C07H13/04
Inventor 陈放张宏唐琳颜钫
Owner SICHUAN UNIV
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