Method for preparing high-purity chlorogenic acid by aluminum salt precipitation

A chlorogenic acid, high-purity technology, applied in the separation/purification of carboxylic acid esters, organic chemistry, etc., can solve the problems of many process steps, long production cycle, and difficulty in realizing industrial production, and achieve simplified process steps, Reduce toxicity and pollution, and facilitate industrial production

Inactive Publication Date: 2012-09-19
SOUTHWEAT UNIV OF SCI & TECH
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  • Abstract
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  • Application Information

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Problems solved by technology

Although high-purity chlorogenic acid can be prepared by chromatography, the cost is high and it is difficult to realize industrial production
Chinese patent CN1687435 A discloses a production process for obtaining high-purity chlorogenic acid by biological compound enzyme treatment. The main steps are: raw materials are pretreated with petroleum ether, biological compound enzyme extraction, acid adjustment of the extract, ethyl acetate extraction, and alkali neutralization After the extraction, the aqueous phase is acid-precipitated, precipitated and recrystallized. Although this process obtains high-purity chlorogenic acid, the biological compound enzyme treatment time is too long, which makes the entire production cycle longer. At the same time, the process operation steps are many and cumbersome. There are many kinds of reagents, not suitable for industrial production
Chinese patent CN1810763 discloses a membrane separation and supercritical CO 2 Extraction combined with the method of refining chlorogenic acid, but this method is still unable to realize industrial production
Wang Hongwu and others used solvent extraction, alkaline Pb(OAc) 2 and KOAc precipitation, redissolution, extraction and recrystallization, the research on the extraction and purification of chlorogenic acids in Eucommia leaves (see "Journal of Jiangxi Normal University" (Natural Science Edition), 1997, 21 (4): 339- 341), but this method uses lead salts for precipitation, there are residues in chlorogenic acid products, and there is serious environmental pollution in lead-containing waste liquid

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Take 5.00 g of eucommia leaf extract powder (30% chlorogenic acid content), add 100 mL of water, 0.003 mol of alum, mix well and centrifuge, wash the precipitate with 50 mL of distilled water, combine the washing liquid with the supernatant, add 1.08 g of sodium hydroxide , adjust the pH to 5, centrifuge to obtain a yellow precipitate, suspend the precipitate in 5 times the volume of ethyl acetate, add concentrated hydrochloric acid until the precipitate is completely dissolved, concentrate the ethyl acetate layer, and crystallize to obtain 950 mg of chlorogenic acid crystals with a purity of 97.9%. The yield of chlorogenic acid was 63.3%.

Embodiment 2

[0022] Take 5.00 g of eucommia leaf extract powder (30% chlorogenic acid content), add 100 mL of water and 0.009 mol of aluminum sulfate, mix well and centrifuge, wash the precipitate with 50 mL of distilled water, combine the washing liquid with the supernatant, add 3.19 g of hydroxide sodium, adjust the pH to 5, centrifuge to obtain a yellow precipitate, suspend the precipitate in 20 times the volume of ethyl acetate, add concentrated sulfuric acid until the precipitate is completely dissolved, concentrate the ethyl acetate layer, and crystallize to obtain 1.013g of chlorogenic acid crystals with a purity of 96.9 %, the yield of chlorogenic acid is 67.5%.

Embodiment 3

[0024] Take 5.00 g of honeysuckle extract powder (10% chlorogenic acid content), add 100 mL of water, 0.003 mol of aluminum sulfate aqueous solution, mix well and centrifuge, wash the precipitate with 50 mL of distilled water, combine the washing liquid with the supernatant, add 1.13 g of hydroxide Potassium, adjust the pH to 5, and centrifuge to obtain a yellow precipitate, which is suspended in 8 times the volume of a mixed solvent (ethyl acetate volume: acetone volume = 100:30), then concentrated hydrochloric acid is added until the precipitate is completely dissolved, and the organic layer is concentrated. Crystallized to obtain 891 mg of chlorogenic acid crystals with a purity of 95.2% and a yield of chlorogenic acid of 59.4%.

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Abstract

The invention discloses a method for preparing high-purity chlorogenic acid by aluminum salt precipitation, which comprises the following steps: (1) impurity removal: mixing a chlorogenic acid extract and water in a material / liquid ratio of 1:10-1:150, and adding an aluminum salt precipitant to precipitate impurities while controlling the pH value at 1-4.5, wherein the unit of the material / liquid ratio is g / ml; (2) precipitation: washing the impurities, merging the washing liquid with the supernatant, and selectvively precipitating chlorogenic acid while controlling the pH value at 4.5-7; (3) dissociation: suspending the precipitate in a cosolvent of which the material / liquid ratio is 1:2-1:50, and adding acid to dissolve the precipitate; and (4) crystallization: concentrating the organic layer solution to 1 / 5-1 / 30 of the original volume, cooling and standing to crystallize, washing the crystals, and drying to obtain the high-purity chlorogenic acid. The method disclosed by the invention is suitable for purifying low-purity chlorogenic acid extract, lowers the production cost, reduces the consumption of the organic solvent, relieves the environmental pollution, and satisfies the requirements for green chemical technology.

Description

technical field [0001] The invention relates to a new method for preparing high-purity chlorogenic acid by selective precipitation, belonging to the field of natural product purification, in particular to a new method for preparing high-purity chlorogenic acid by aluminum salt precipitation. Background technique [0002] Chlorogenic acid is mainly distributed in plants such as Lonicera, Rosaceae, Compositae, Rubiaceae and Eucommiaceae. It is the main component of traditional Chinese medicines such as Eucommia and honeysuckle for clearing away heat, detoxifying, anti-inflammatory and antibacterial. A phenylpropanoid compound formed by the oxalate pathway, molecular formula C 16 h 18 o 9 , with a molecular weight of 354.90, easily hydrolyzed under alkaline or high temperature conditions. Many studies have shown that chlorogenic acid has pharmacological effects such as antibacterial, antiviral, antioxidative, scavenging free radicals, immune regulation, increasing white bloo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/732C07C67/48
Inventor 袁小红陈粟源徐春霞刘卓黄毅侯大斌
Owner SOUTHWEAT UNIV OF SCI & TECH
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