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Method for preparing gardenia blue by utilizing phase-transfer catalysis

A technology of gardenia blue pigment and phase transfer catalysis, which is applied in the field of preparation of gardenia blue pigment by phase transfer catalysis, can solve the problems of low solubility of intermediate product genipin, easy occurrence of side reactions such as hydrolysis, and influence on yield, etc., to achieve The effect of avoiding side reactions, improving conversion rate and simplifying reaction process

Inactive Publication Date: 2015-06-17
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that because the intermediate product genipin has low solubility and is prone to side reactions such as hydrolysis, which affects the yield; at the same time, the genipin produced by the reaction has competitive inhibition on the hydrolysis of geniposide, which is not conducive to the progress of the reaction.

Method used

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  • Method for preparing gardenia blue by utilizing phase-transfer catalysis
  • Method for preparing gardenia blue by utilizing phase-transfer catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Fresh gardenia fruit (Zhejiang Tianlu Biotechnology Co., Ltd.), wash off the dirt attached to the surface with water, peel and crush into gardenia fruit powder, and mix the fruit powder with 30 (v / v)% ethanol aqueous solution at a mass ratio of 1:5 Sonicate (100W, 20min, 3 times), combine the extracts, concentrate under reduced pressure in vacuo to remove ethanol, recover the solvent, and dry the concentrated solid to obtain the crude geniposide.

[0032] Aqueous phase (165μg / mL crude geniposide + 0.946U / mL β-glucosidase, pH4.5)-n-hexanol (ratio 1:1), hydrolyzed at 45°C for 40min (220rpm), the concentration of geniposide was measured by HPLC The conversion rate was 91%, and the yield of genipin was 88%. Add 0.05mol / L glycine aqueous solution (v / v2:1) to the extracted organic phase, and develop color reaction in a constant temperature water bath at 80°C for 20min to obtain a bright gardenia blue pigment aqueous solution, which is vacuum-dried (400mmHg, 65°C , 5h) to obt...

Embodiment 2

[0034] Fresh gardenia fruit (Zhejiang Tianlu Biotechnology Co., Ltd.), washed with water to remove the dirt attached to the surface, peeled and crushed into gardenia fruit powder, fruit powder and 40% ethanol aqueous solution in a mass ratio of 1:5 and ultrasonically (120W, 20min , 4 times) to combine the extracts, and then use vacuum to remove ethanol and recover the solvent to obtain the geniposide extract.

[0035] Aqueous phase (200μg / mL geniposide + 2.838U / mL β-glucosidase, pH 4.5) - ethyl acetate (ratio 1:3), hydrolyzed at 50°C for 80min (220rpm), HPLC measured geniposide The conversion rate was 93%, and the yield of genipin was 92%. Add 0.1 mol / L glycine solution (v / v 2:1) to the extracted organic phase, develop a color reaction in a 90°C constant temperature water bath for 40min, and obtain a bright gardenia blue pigment solution, vacuum dry (400mmHg, 70°C , 6h) to obtain gardenia blue pigment powder, the measured pigment color value is 180.

Embodiment 3

[0037] Fresh gardenia fruit (Zhejiang Tianlu Biotechnology Co., Ltd.), washed with water to remove the dirt attached to the surface, peeled and crushed into gardenia fruit powder, fruit powder and 40% ethanol aqueous solution in a mass ratio of 1:8 and ultrasonically (140W, 20min , 4 times) to combine the extracts, and then use vacuum to remove ethanol and recover the solvent to obtain the geniposide extract.

[0038]Aqueous phase (2000μg / mL geniposide + 4.73U / mL β-glucosidase, pH5.0) - n-octanol (ratio 1:2), hydrolyzed at 50°C for 80min (180rpm), HPLC measured geniposide The conversion rate was 94.8%, and the yield of genipin was 93.1%. Add 0.2 mol / L glycine solution (v / v 2:1) to the extracted organic phase, and develop a color reaction in a constant temperature water bath at 100°C for 30 minutes to obtain a bright gardenia blue pigment solution, which is vacuum-dried (450mmHg, 70°C , 6.5h) to obtain gardenia blue pigment powder, the measured pigment color value is 185.

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Abstract

The invention discloses a method for preparing gardenia blue pigment using phase transfer catalysis. The gardenia fruit is peeled and mashed into powder, and an ethanol aqueous solution is added for ultrasonic extraction and filtration. The filtrate is concentrated under reduced pressure to recover ethanol. The concentrated solid is processed After drying and dissolving in water, a crude gardeniposide aqueous solution is obtained; the crude gardeniposide aqueous solution is mixed with the β-glucosidase solution as the water phase, and the organic solvent is used as the organic phase. The intermediate product Jing is obtained by catalyzing the hydrolysis reaction under shaking or stirring conditions. Nipe; take the organic phase, add the aqueous solution of hydrophilic amino acid, and react under shaking or stirring conditions to obtain gardenia blue pigment; take the aqueous phase, concentrate and vacuum dry to obtain gardenia blue pigment powder. This method uses reaction-extraction technology to effectively eliminate the product inhibition and product degradation side reactions of conventional methods for preparing genipine, and the conversion rate of gardeniposide is high. At the same time, high-purity gardenia blue can be obtained by back-extraction of amino acid solution, and the organic solvent can be recycled.

Description

technical field [0001] The invention relates to the preparation of natural pigments in the fields of plant extraction, biocatalysis and food additives, in particular to a method for preparing gardenia blue pigments by phase transfer catalysis. Background technique [0002] Gardenia is a Rubiaceae plant, also known as yellow gardenia, mountain branch, red gardenia, white cicada, long oval or oval, mainly produced in southern and central southern China. There are many chemical components in Gardenia, mainly containing crocetin, crocetin and its derivatives, and 11 kinds of iridoid glycosides mainly composed of geniposide, as well as chlorogenic acid, tannin, Pectin, volatile oil, mannitol, etc.; a variety of pigments can be extracted from gardenia fruit for food coloring, not only comparable to the corresponding synthetic pigments, but also has curative effect. [0003] Gardenia blue pigment is a natural pigment, which uses geniposide in gardenia fruit as raw material, and is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/12
Inventor 姚忠万丽花孙芸仲兆祥
Owner NANJING TECH UNIV
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