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A technology of crocetin and cis-trans isomerization, applied in the field of natural medicinal chemistry, can solve the problems of large ethanol consumption, insoluble crocetin in ethanol, and large alkali consumption
Active Publication Date: 2019-01-11
嘉文丽(福建)化妆品有限公司
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In actual operation, it is found that crocetin is insoluble in ethanol, so the actual consumption of ethanol is very large
Patent 201710227023.X uses high-concentration alkali solution recrystallization to obtain high-purity crocetin. According to the estimation of Example 2, 10.0 g of crocetin with a purity of 10.6% is recrystallized and purified to 99.4% (0.93g). It needs to consume more than 100g of potassium hydroxide. This method consumes a lot of alkali and easily produces a large amount of alkaline waste liquid
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Embodiment 1
[0071] (1) Get 20g of crocetin crude product (the E-crocetin content is 62% after detection, Z-crocetin content is 8.3%) and 1500mL pure water are poured into beaker, regulate pH with sodium hydroxide alkali and be 11, heating promotes crocetin Dissolve the crude safflower acid, filter and discard the contents while it is hot;
[0072] (2) Slowly drop 10 mL of 5% calcium chloride into the filtrate, heat and crystallize at 60° C. for 4 h;
[0073] (3) filter;
[0074] (4) The filter residue is rinsed twice with 75% ethanol, then acidified with 200mL of 1% citric acid, kept at 60°C for 2h, filtered, washed with pure water, and the filter residue is vacuum-dried to obtain all-trans crocetin 12.1g (through HPLC detection, the purity is 97%);
[0075] (5) Adding 5% citric acid to the filtrate of (3) until the pH is 4, insulated for 2h, filtered, rinsed with pure water, and the filter residue was vacuum-dried to obtain cis-crocetin 1.62g (detected by HPLC, the purity was 94%) ). ...
Embodiment 2
[0077] (1) Take 100g of gardenia yellow (color value is 405) and 800mL of pure water in a beaker, heat to 70°C to dissolve completely; slowly add 50mL of 20% sodium hydroxide into the gardenia yellow solution, keep stirring, 60 Insulate at ℃ for 30 minutes; add 10% hydrochloric acid dropwise to the reaction solution until the pH is 4; insulate for 1 hour to age the precipitate; filter with suction, wash the filter residue twice with pure water, and the dark red solid (after drying, the crude crocetin acid ).
[0078] (2) Transfer the dark red solid in (1) and 1000 mL of pure water into a beaker, adjust the pH to 10-11 with 10% sodium hydroxide, heat to promote dissolution, and filter to remove insoluble matter;
[0079] (3) Slowly add 4mL 5% CaCl 2 Solution, keep warm at 60°C for 4h;
[0080] (4) filter;
[0081] (5) The filter residue is rinsed twice with 80% ethanol, then acidified with 150mL of 1% citric acid, kept at 60°C for 2h, filtered, rinsed with pure water, and th...
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Abstract
The invention relates to the technical field of extraction and separation of natural plant active components, and particularly relates to a separation method of cis-trans isomerism crocetin. Crocetinbelongs to a carotenoid compound, has the effects of being strong in antioxidant activity, protecting heart and blood vessels and inhibiting skin cancer [1], and has potential application value in medicine and skin care products. Crocetin and glycoside thereof mainly exist in gardenia fruit and saffron. The gardenia fruit is low in value and rich in source can provide rich material source for crocetin, but has a cis-trans isomer. The invention provides a separation method of the cis-trans isomerism crocetin, by utilizing the difference of combining capacity of cis-trans isomerism crocetin withcalcium ions, all-trans-crocetin easily forms a regular molecule compound with Ca2+ ions, that is, all-trans-crocetin generates crystallization (precipitation) easily, while cis-crocetin cannot forma regular molecule compound with Ca2+ ions, that is, cis-crocetin does not form precipitation with Ca2+ easily, all trans-crocetin can be effectively separated from cis-crocetin.
Description
technical field [0001] The invention belongs to the technical field of natural medicinal chemistry, relates to the technical field of extraction and separation of natural plant active ingredients, and in particular to a method for separating cis-trans isomeric crocetin. Background technique [0002] Crocetin is a carotenoid compound, and generally exists in plants in the form of gentiobioside (ie, crocin, crocin), and is mainly distributed in saffron and gardenia. Crocetin has strong antioxidant activity, cardiovascular protection, and inhibition of skin cancer[1], etc. It has potential application value in medicine and skin care products. Ohba T[2] found that crocetin can protect human skin fibroblasts from UVA when studying the effect of UVA on human skin fibroblasts. The mechanism is that crocetin can reduce the reactive oxygen species caused by UVA. generation. Yinghua Song[3] found that crocetin can reverse skin fibrosis when studying the effect of crocetin on sclerod...
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