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D-biotin purification process

A purification method and biotin technology, applied in the direction of organic chemistry, can solve problems such as incomplete extraction of chloroform, unqualified d-biotin products, and inability to remove l-biotin, so as to reduce production costs, ensure quality, and effectively The effect of removal

Active Publication Date: 2008-06-11
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the diversity of impurities, chloroform extraction is incomplete to remove l-biotin, and since the optical rotation of d-biotin containing monobenzyl biotin cancels out the optical rotation of a small amount of l-biotin, it may cause The illusion of qualified optical rotation of the product, resulting in the production of unqualified d-biotin products

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Biotin crude product 30g (HPLC detection contains 5% dibenzyl biotin, 7% monobenzyl biotin, 85% biotin. [α] D 25 =79.5° (c=1.0, 0.1N NaOH)), 800ml of 95% medicinal ethanol, 30ml of glacial acetic acid was heated and refluxed, after it was completely dissolved, 1.5g of active carbon was dropped into it while it was hot, stirred for 0.5 hour, filtered, and the filter cake was refluxed with 95% Wash with 100ml of medicinal ethanol, freeze the filtrate overnight, and precipitate white needle crystals, filter and dry in vacuum at 80°C to obtain 25g of d-biotin (HPLC biotin content up to 98%, [α] D 25 =83.2° (c=1.0, 0.1N NaOH)), d-biotin is an unqualified product because of the problem of optical rotation.

Embodiment 2

[0014] Take 25g (0.102mol) of biotin prepared in Example 1, 20g (0.115mol) of l-arginine, 150ml of deionized water, and 300ml of isopropanol, stir and slowly heat up to 80°C to obtain a clear colorless liquid, which is kept for 1 Hours later, first use a water bath, then slowly cool down to 0°C with ice water, let stand at a constant temperature at 0°C overnight, and precipitate biotin arginine salt, filter the filter cake and rinse twice with 50ml of absolute ethanol, and dry to obtain 41g (0.098mol ), add 1000ml of 80% medicinal ethanol to dissolve, heat in a water bath to 80°C, add 17.5% hydrochloric acid dropwise, the measured pH is about 3, continue to heat up and reflux, add 1.0g of activated carbon, filter, the filtrate freezes and crystallizes, and d-biotin 23.2 g, 93.2% yield, HPLC detection content is 99.5% (〔α〕 D 25 =90.4° (c=1.0, 0.1N NaOH)).

Embodiment 3

[0016] Biotin crude product 40g (HPLC detection contains 2% dibenzyl biotin, 5% monobenzyl biotin, 88% biotin [α] D 25 =75° (c=1.0, 0.1N NaOH)), 600ml of 95% medicinal ethanol, 80ml of glacial acetic acid was heated and refluxed, after completely dissolving, 2g of active carbon was dropped into while hot, stirred for 0.5 hour, filtered, and the filter cake was washed with 95% medicinal Wash with 100ml of ethanol, freeze the filtrate overnight, and precipitate white needle-like crystals. Filtration and vacuum drying at 80°C yielded 35g of biotin (HPLC biotin content up to 98.8%, [α] D 25 =80.6°(c=1.0, 0.1N NaOH), smaller than standard [α] D 25 +89°~+93° (c=1.0, 0.1NNaOH)).

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Abstract

The invention discloses a purification method of d-biotin, while prior art can not remove I-biotin to produce disqualified d-biotin product. The invention uses the recrystallization of the mixture solvent of lower alkyl alcohol and glacial acetic acid to purify d-biotin with foreigner materials, to remove foreigner materials as bis-benzyl biotin and single-benzyl biotin. And when the optical rotation of the product in procedure step is disqualified, in water and lower alkyl alcohol, the invention arranges chiral induction resolving agent I-arginine and d-biotin with disqualified optical rotation to be mixed, dissolved, frozen, crystallized and filtered, to remove foreigner material as I-biotin, heats and dissolves the filter cake via water or lower alkyl alcohol, adjusts pH value via diluted acid until 2-5, freezes and crystallizes, filters to obtain the filter cake as d-biotin pure product. The invention precipitates solid d-biotin and leaves I-biotin in filter liquor, to effectively remove I-biotin and confirm the quality of medical d-biotin.

Description

technical field [0001] The invention relates to a method for purifying d-biotin. Background technique [0002] D-biotin is a chemical substance with a ring structure, which has a structure ring of Thiophene. This chemical substance has eight isomers, but only d-biotin exists In nature, there is also the function of vitamins, d-biotin is active, odorless and tasteless, colorless to nearly colorless crystalline powder. Solubility at 25°C (mg / 100ml): water-22; 95% ethanol-80, almost insoluble in ether and chloroform, easily soluble in hot water and dilute lye, insoluble in other commonly used organic solvents. d-biotin will be destroyed only after treatment with strong acid, strong alkali, formaldehyde and ultraviolet light. Especially in case of strong alkali or oxidizing agent, it will decompose obviously. Melting point is 228~232℃ (decomposition), specific rotation [α] D 25 +89°~+93°. [0003] Dibenzylbiotin [α] exists in the chemical synthesis of d-biotin D 25 =-26....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 陈建辉王红卫丁建清
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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