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Preparation method of high-purity trans-crocetin

A technology of trans-crocetin and crocetin, which is applied in the preparation of carboxylate, organic compound, chemical instruments and methods, etc., can solve the problems of easily damaged sample structure, high solvent, residue, etc., and achieve The production process is simple, the conditions are easy to control, and the effect of small environmental impact

Active Publication Date: 2015-09-02
苏州衷中医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, N, N-dimethylformamide and dimethyl sulfoxide crystals have relatively high boiling points, and the sample structure is easily destroyed during the recovery process, and the final product may have high solvent residues

Method used

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  • Preparation method of high-purity trans-crocetin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Preparation of crude crocetin acid: Take 500 g of gardenia yellow pigment with a commercially available color price of 60, add 10 L of 2% sodium hydroxide aqueous solution to dissolve, hydrolyze at 60 °C for 2.5 hours, add hydrochloric acid with a concentration of 10% by mass to adjust When the pH value reaches 3.0, let it stand for 24 hours to precipitate a precipitate, centrifuge, and wash the precipitate with water until the pH value of the washed water is neutral. The resulting precipitate was vacuum-dried at 60° C. for 3 hours to obtain 20.5 g of crude crocetin, which was detected by HPLC with a mass percentage of trans-crocetin of 14.6%.

[0027] Take 5.0 g of the crude crocetin prepared in this example, add 300 mL of pyridine, heat to 80° C. to dissolve, and remove insoluble impurities by filtration while hot. The filtrate was left at room temperature (20-25°C) for 24 hours, and crystals of trans-crocetin pyridinium salt were precipitated. Recrystallize trans-cr...

Embodiment 2

[0029] Take 5.0 g of the crude crocetin prepared in Example 1, add 300 mL of 80% pyridine aqueous solution, heat to 70° C. to dissolve, and remove insoluble impurities by filtration while hot. Place the filtrate in the refrigerated layer of the refrigerator (2-8°C) for 24 hours to precipitate trans-crocetin pyridinium salt crystals. Recrystallize the trans-crocetin pyridinium salt crystals with an aqueous pyridine solution with a concentration of 80% by mass 3 times (each time the amount of solvent used is 250 times that of the crystal), and high-purity trans-crocetin pyridinium salt was obtained, and its purity was 99.4% as detected by HPLC. Add an aqueous ethanol solution with a volume percentage concentration of 95% to the high-purity trans-crocetin pyridinium salt, heat until completely dissolved, adjust the pH value to 2.0 with a mass percentage concentration of 10% hydrochloric acid, and let it stand for 24 hours Precipitate trans-crocetin, centrifuge, take the precipita...

Embodiment 3

[0031] Take 5.0 g of the crude crocetin prepared in Example 1, add 300 mL of ethanol-based pyridine solution (pyridine mass percentage is 60%), heat to 80°C to dissolve the solid, and remove insoluble impurities by filtration while hot. The filtrate was placed in the refrigerator (2-8°C) for 24 hours, and crystals of trans-crocetin pyridinium salt were precipitated. Recrystallize trans-crocetin pyridinium salt crystals with ethanol pyridine solution (pyridine mass percentage is 60%) for 3 times (each time the amount of solvent is 300 times the crystal weight), to obtain high-purity trans-crocetin Acid pyridinium salt, its purity was 98.8% as detected by HPLC. Suspend high-purity trans-crocetin pyridinium salt in 1000ml of 2% hydrochloric acid aqueous solution, then extract with ethyl acetate until the acidic aqueous layer is nearly colorless, combine the ethyl acetate layers, and wash with water Until the eluate is neutral, trans-crocetin is obtained after recovering ethyl ac...

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Abstract

The invention discloses a preparation method for high-purity trans-crocetin, which belongs to the field of extraction and separation of Chinese medicinal herbs. The method comprises the following specific steps of: transforming trans-crocetin in crude crocetin into trans-crocetin pyridinium, and crystalizing and recrystallizing through pyridine or a pyridine-containing solution to obtain trans-crocetin pyridinium; and making the trans-crocetin pyridinium react with an acid to obtain the high-purity trans-crocetin. The method disclosed by the invention has the advantage of easiness for repeating operation steps, controlling operation conditions, recovering crystalizing solvents and industrial amplifying in batch; and the purity of a final product, i.e., the trans-crocetin can be over 98 percent.

Description

technical field [0001] The invention belongs to the technical field of extraction and separation of Chinese herbal medicines, and in particular relates to a method for further separating high-purity trans-crocetin from crude crocetin. Background technique [0002] Crocetin is a carotenoid component naturally present in plants such as saffron and gardenia. It has a polyunsaturated conjugated enoic acid structure and is divided into trans-crocetin and 13-cis-crocetin Two types, except for a small part in free state, most of them exist in plants such as saffron and gardenia in the form of ester glycosides (crocin and gardenia yellow pigment) combined with sugar. Trans-crocetin has a wide range of pharmacological activities, including anti-tumor, anti-atherosclerosis, anti-hypertension and treatment of hemorrhagic shock, as well as anti-oxidation, liver protection and choleretic effects. The structural formula of trans crocetin is as follows: [0003] [0004] The binding e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C57/13C07C51/487
Inventor 石荣火陈文星严燕青叶华
Owner 苏州衷中医药科技有限公司
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