Method for preparing capsicine monomer and dihydrocapsaicin std monomer

A technology of dihydrocapsaicin and capsaicin, applied in the field of biomedicine, can solve problems such as unfavorable industrialized production, cumbersome process steps, unfavorable large-scale production, etc., achieves solvent consumption, non-toxicity, environmental protection, high product yield and purity, and is suitable for large-scale production. The effect of mass production

Active Publication Date: 2012-05-02
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Due to the differences in the content of each component of capsaicin in peppers from different origins and varieties, each component cannot be accurately quantified and the quality is difficult to control, which leads to the limitation of the application of capsaicin in the field of medicine; in addition, due to capsaicin monomer and other The chemical structure of each component is very similar, and the most important capsaicin and dihydrocapsaicin are only the difference between the sixth single and double bonds in the carbon chain, so it is very difficult to separate them
Patent CN200610068854.9 reports the preparation of capsaicin monomer by affinity column chromatography. This method requires expensive silver salt treatment of silica gel, and silica gel cannot be regenerated and reused. A large amount of flammable and explosive organic solvents are used in the extraction process, which is harmful to the environment. Cause pollution etc., make production cost high; Patent CN200710114310.6 has reported three kinds of monomers of capsaicin, dihydrocapsaicin and nordihydrocapsaicin prepared by high-speed countercurrent chromatography, but this method processing capacity is little, and cycle is longer, It is not conducive to the realization of industrialized production; patent 200810060471.6 reports the preparation of capsaicin monomer by simulated moving bed chromatography. This method requires simulated moving bed chromatography system. The equipment of this system is relatively expensive and the processing capacity is small, which makes it difficult to expand production and is not conducive to realizing large-scale Production; patent 200910148379.X reports the preparation of capsaicin, dihydrocapsaicin and nordihydrocapsaicin three monomers by macroporous adsorption resin method, the process steps are cumbersome, consume a large amount of solvent, and the production cost is high

Method used

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  • Method for preparing capsicine monomer and dihydrocapsaicin std monomer
  • Method for preparing capsicine monomer and dihydrocapsaicin std monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Take homemade capsaicin, then add methanol and water to prepare a capsaicin raw material solution with a methanol content of 20% and a concentration of 1.04 mg / mL.

[0025] (2) Pack the pretreated ODS into the column by wet method, the column diameter is 1.1cm, the packing height is 60cm, and 10mL of sample is loaded at a flow rate of 0.5mL / min.

[0026] (3) After the raw material is completely absorbed, elute the column with 180mL of 75% methanol at a flow rate of 0.5ml / min, collect in sections, combine the capsaicin and dihydrocapsaicin components separately, and analyze the components by high performance liquid chromatography See Table 1 for the purity and yield (relative to the raw material solution).

[0027] (4) After removing the solvent from the collected components, recrystallize with ethanol, and analyze the crystal purity and yield (relative to the raw material liquid) by high performance liquid chromatography, see Table 2.

Embodiment 2

[0029] (1) Take homemade capsaicin, then add methanol and water to prepare a capsaicin raw material solution with a methanol content of 30% and a concentration of 3.36 mg / mL.

[0030] (2) Pack the pretreated ODS into the column by wet method, the column diameter is 1.6cm, the packing height is 70cm, and 300mL of sample is loaded at a flow rate of 2.0mL / min.

[0031] (3) After the raw material is completely absorbed, elute the column with 400mL of 70% methanol at a flow rate of 1.5ml / min, collect in sections, combine the capsaicin and dihydrocapsaicin components separately, and analyze the components by high performance liquid chromatography The purity and yield are shown in Table 1.

[0032] (4) After removing the solvent from the collected components, recrystallize with ethanol, and analyze the crystal purity and yield by high performance liquid chromatography, see Table 2.

Embodiment 3

[0034] (1) Take homemade capsaicin, then add methanol and water to prepare a capsaicin raw material solution with a methanol content of 35% and a concentration of 4.71 mg / mL.

[0035] (2) Pack the pretreated ODS into the column by wet method, the column diameter is 4.0cm, the packing height is 70cm, and 2000mL of sample is loaded at a flow rate of 5.0mL / min.

[0036] (3) After the raw material is completely absorbed, elute the column with 2500mL of 70% methanol at a flow rate of 5.0ml / min, collect in sections, combine the capsaicin and dihydrocapsaicin components separately, and analyze the group by high performance liquid chromatography The purity and yield of the fractions are shown in Table 1.

[0037] (4) After removing the solvent from the collected components, recrystallize with ethanol, and analyze the crystal purity and yield by high performance liquid chromatography, see Table 2.

[0038] Table 1 Experimental data of components analyzed by high performance liquid chr...

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Abstract

The invention belongs to the field of biomedicine and particularly discloses a method for preparing a capsicine monomer and a dihydrocapsaicin std monomer. In the method, the capsicine monomer and the dihydrocapsaicin std monomer are separated out through self-control reversed-phase chromatographic column; and by utilizing an ODS (ozone depleting substance) filler as a stationary phase and a methanol / water mixed liquid as a mobile phase, preparation is carried out under the conditions of optimal sample loading amount and elution flow velocity, products are separately collected, a capsicine monomer crude product and a dihydrocapsaicin std monomer crude product are separated out, and the monomer crude products are recrystallized to obtain the high-purity capsicine monomer and the high-purity dihydrocapsaicin std monomer. The method disclosed by the invention has the advantages that the process is simple, equipment is cheap, the manufacturing cost is low, the solvent consumption is less, nontoxicity and environmental protection are achieved, the product yield and purity are higher, the processing amount is high, and the method is suitable for large-scale production.

Description

(1) Technical field [0001] The invention belongs to the field of biomedicine, in particular to a method for preparing capsaicin and dihydrocapsaicin monomers. (2) Background technology [0002] Capsicum (Capsicum) is the fruit of pepper in the family Solanaceae. Capsaicin (also known as capsaicinoids, capsaicinoids) is a class of extremely pungent vanilla amide alkaloids, which are the main spicy chemical components in pepper fruits. Including: Capsaicin, Dihydrocapsaicin, Nordihydrocapsaicin, Homocapsaicin, Homodihydrocapsaicin, the content of these five components accounts for 99% %, wherein the two components of capsaicin and dihydrocapsaicin account for more than 90%. [0003] Capsaicin has pharmacological effects such as anti-inflammatory and analgesic, promoting fat metabolism, tearing and sneezing, promoting appetite, improving digestion, antibacterial and insecticidal, and selective to neurotransmitters; in addition, capsaicin is also used in the production of s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/24C07C233/20C07C233/18
Inventor 崔波孙菲菲檀琮萍
Owner QILU UNIV OF TECH
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