CN102432489B - Method for preparing capsicine monomer and dihydrocapsaicin std monomer - Google Patents
Method for preparing capsicine monomer and dihydrocapsaicin std monomer Download PDFInfo
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- CN102432489B CN102432489B CN201110385818.6A CN201110385818A CN102432489B CN 102432489 B CN102432489 B CN 102432489B CN 201110385818 A CN201110385818 A CN 201110385818A CN 102432489 B CN102432489 B CN 102432489B
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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
The invention belongs to biomedicine field, particularly a kind of method of preparing capsicine and Dihydrocapsaicin monomer.
(2) background technology
The fruit that capsicum (Capsicum) is solanaceae plant pepper, capsaicine (claims again capsaicin compound, Capsaicinoids Capsaicinoids) be the vanilla amide alkaloid that a class is extremely pungent, for main chemical compositions pungent in pepper fruit, mainly comprise: capsicine (Capsaicin), Dihydrocapsaicin (Dihydrocapsaicin), Nordihydrocapsaicin (Nordihydrocapsaicin), homocpsaicin (Homocapsaicin), Homodihydrocapsaicin I (Homodihydrocapsaicin), the content of these five kinds of components accounts for 99%, wherein two kinds of compositions of capsicine and Dihydrocapsaicin account for more than 90%.
Capsaicine has anti-inflammatory analgesic, promotes metabolism of fat, tear-gas to urge and sneezing, promote appetite, improves digestion, antibacterial desinsection and the pharmacological actions such as selectivity to neurotransmitter; Capsaicine is also for the production of pungent antifouling varnish and anti-ant, anti-rodent repellent, as novel green agricultural chemicals, for the manufacture of multiple fields such as tear bomb, tear-gas rifle and defensive weapons in addition.In the international market, there is certain breach in the supply of capsicine, in particular for high-purity capsaicin product pharmaceutically, this part product processing technique difficulty is large, selling price is also high, and along with capsicine is deeply the promoting the use of of each field such as medical, agriculture, market outlook are more optimistic.
Because the content of each component of capsaicine in the capsicum of the different places of production and kind there are differences, each component can not accurate quantitative analysis, and difficult quality is controlled, and this causes capsaicine to be restricted in the application of field of medicaments; In addition, because the chemical structure between capsaicin monomer and other each components is closely similar, the just difference of the 6th Dan Shuanjian of carbochain of topmost capsicine and Dihydrocapsaicin, thereby its separating difficulty is very large.Patent CN200610068854.9 has reported that affinity column chromatography legal system is for capsaicin monomer, this method need to be carried out expensive silver salt processing to silica gel, silica gel can not be regenerated and be reused, leaching process is used a large amount of inflammable and explosive organic solvents, to environment etc., production cost can be in any more; Patent CN200710114310.6 has reported that high-speed countercurrent chromatography prepares capsicine, Dihydrocapsaicin and three kinds of monomers of Nordihydrocapsaicin, but this method treatment capacity is little, and the cycle is longer, is unfavorable for realizing suitability for industrialized production; Patent 200810060471.6 has reported that simulated moving bed chromatography legal system is for capsaicin monomer, and the method needs simulated moving bed chromatography system, and this system device is more expensive, and treatment capacity is little, makes expanding production difficulty, is unfavorable for realizing scale operation; Patent 200910148379.X has reported that Flavonoids by Macroporous Adsorption Resin prepares capsicine, Dihydrocapsaicin and three kinds of monomers of Nordihydrocapsaicin, and this processing step is loaded down with trivial details, consumes a large amount of solvents, and production cost is high.
(3) summary of the invention
The present invention, in order to make up the deficiencies in the prior art, provides a kind of method of preparing capsicine and Dihydrocapsaicin monomer that technique is simple, production cost is low.
The present invention is achieved through the following technical solutions:
A method of preparing capsicine and Dihydrocapsaicin monomer, take capsaicine as raw material, mainly comprises the steps:
(1) in capsaicine, add first alcohol and water, be mixed with capsaicine stock liquid, the concentration of stock liquid is 0.5 ~ 5mg/ml, and the concentration of methyl alcohol is 20 ~ 40%;
(2) by the direct wet method upper prop of stock liquid, reverse-phase chromatography column packing is Octadecylsilane bonded phase silica gel ODS, and aspect ratio is 10 ~ 60, and loading flow velocity is 0.5 ~ 5ml/min, and adsorptive capacity is 1 ~ 5g capsaicine/10gODS, and applied sample amount is 0.01 ~ 10g;
(3) the methanol solution wash-out that is 70 ~ 75% by concentration, elution flow rate is 0.5 ~ 5ml/min, fraction collection;
(4) elutriant fraction collection being arrived respectively concentrating under reduced pressure, except desolventizing, obtains respectively capsicine and Dihydrocapsaicin crude product;
(5) by dissolving crude product in dehydrated alcohol, carry out recrystallization, filter dry capsicine of monomer and the monomer Dihydrocapsaicin crystal of obtaining.
The present invention varies in size according to the hydrophobicity of capsicine and Dihydrocapsaicin, utilizes reverse-phase chromatographic column to carry out separation.With in elutriant elution process, the impurity that the larger hydrophobicity of polarity is less is not easy to be combined with nonpolar stationary phase, so be first eluted, the capsicine that then polarity is little elutes, and the Dihydrocapsaicin of the hydrophobicity maximum of polarity minimum finally elutes.
More excellent scheme of the present invention is:
Described ODS reverse-phase chromatographic column is reusable after Mathanol regenerating, and the consumption of solvent methanol is 2 ~ 4BV.
In step (1), the purity of described capsaicine is more than 70%.
In step (2), reverse-phase chromatographic column pillar be glass column, synthetic glass post or stainless steel column, chromatographic column filler is the ODS filler of particle diameter 40 ~ 60 μ m.
In step (4), the vacuum tightness of concentrating under reduced pressure is 0.1Mpa, and temperature is 35 ~ 55 ℃.
In step (5), the temperature of recrystallization is 4 ℃, and crystallization time is 9h.
In above-mentioned technique, the analytical procedure of capsaicine is high performance liquid chromatography, and analysis condition is: chromatographic column Agilent HC-C
18, 4.6mm * 250mm, 5 μ m; Detector: UV-detector; Moving phase: methanol/water (volume ratio 70/30); Flow velocity: 0.8mL/min; Detect wavelength: 280nm; Column temperature: 25 ℃; Sample size: 10uL.
Adopt the present invention to utilize reverse-phase chromatography to prepare capsicine of monomer and monomer Dihydrocapsaicin, the simple easy handling of technical process, only need just can from capsaicine, isolate respectively capsicine of monomer and monomer Dihydrocapsaicin through one-step elution, equipment cheap and simple is easy to realize, do not need the equipment of large-scale costliness can complete production, one time to produce amount is large, yield is all more than 90%, after recrystallization, purity all reaches more than 98%, solvent consumption is few, production cost is low, and there is not organic solvent residual problem in products obtained therefrom, asepsis environment-protecting, after filler is renewable, reuse, and experiment further can be amplified, realize more massive suitability for industrialized production, the present invention is a kind of simple production technique of preparing in a large number capsicine and Dihydrocapsaicin of green.
Technique of the present invention is simple, and equipment is cheap, and production cost is low, the few and asepsis environment-protecting of solvent consumption, and product yield purity is all higher, and treatment capacity is large, is applicable to scale operation.
(4) embodiment
Embodiment 1:
(1) take from capsaicine processed, then add first alcohol and water, being made into methanol content is 20%, the capsaicine stock liquid that concentration is 1.04mg/mL.
(2) the good ODS wet method of pre-treatment is installed in pillar, pillar diameter 1.1cm, packed height 60cm, with the flow velocity loading 10mL of 0.5mL/min.
(3) after all adsorbing, raw material uses the methanol-eluted fractions pillar of 180mL75%, flow velocity is 0.5ml/min, and fraction collection merges separately capsicine component and Dihydrocapsaicin component, the purity of high-efficient liquid phase chromatogram technique analysis component and yield (with respect to stock liquid), in Table one.
(4) will collect component except after desolventizing, with ethyl alcohol recrystallization, high-efficient liquid phase chromatogram technique analysis crystal purity and yield (with respect to stock liquid), in Table two.
Embodiment 2:
(1) take from capsaicine processed, then add first alcohol and water, being made into methanol content is 30%, the capsaicine stock liquid that concentration is 3.36mg/mL.
(2) the good ODS wet method of pre-treatment is installed in pillar, pillar diameter 1.6cm, packed height 70cm, with the flow velocity loading 300mL of 2.0mL/min.
(3) after raw material all adsorbs, use the methanol-eluted fractions pillar of 400mL70%, flow velocity is 1.5ml/min, and fraction collection merges separately capsicine component and Dihydrocapsaicin component, and the purity of high-efficient liquid phase chromatogram technique analysis component and yield, in Table one.
(4) will collect component except after desolventizing, with ethyl alcohol recrystallization, high-efficient liquid phase chromatogram technique analysis crystal purity and yield, in Table two.
Embodiment 3:
(1) take from capsaicine processed, then add first alcohol and water, being made into methanol content is 35%, the capsaicine stock liquid that concentration is 4.71mg/mL.
(2) the good ODS wet method of pre-treatment is installed in pillar, pillar diameter 4.0cm, packed height 70cm, with the flow velocity loading 2000mL of 5.0mL/min.
(3) after raw material all adsorbs, use the methanol-eluted fractions pillar of 2500mL 70%, flow velocity is 5.0ml/min, and fraction collection merges separately capsicine component and Dihydrocapsaicin component, and the purity of high-efficient liquid phase chromatogram technique analysis component and yield, in Table one.
(4) will collect component except after desolventizing, with ethyl alcohol recrystallization, high-efficient liquid phase chromatogram technique analysis crystal purity and yield, in Table two.
Table one high-efficient liquid phase chromatogram technique analysis component experimental data
Table two high-efficient liquid phase chromatogram technique analysis crystal experimental data
Claims (6)
1. a method of preparing capsicine and Dihydrocapsaicin monomer, take capsaicine as raw material, it is characterized by, and mainly comprises the steps:
(1) in capsaicine, add first alcohol and water, be mixed with capsaicine stock liquid, the concentration of stock liquid is 0.5 ~ 5mg/ml, and the concentration of methyl alcohol is 20 ~ 40%;
(2) by the direct wet method upper prop of stock liquid, reverse-phase chromatography column packing is Octadecylsilane bonded phase silica gel ODS, and aspect ratio is 10 ~ 60, and loading flow velocity is 0.5 ~ 5ml/min, and adsorptive capacity is 1 ~ 5g capsaicine/10gODS, and applied sample amount is 0.01 ~ 10g; Reverse-phase chromatographic column pillar be glass column, synthetic glass post or stainless steel column, chromatographic column filler is the ODS filler of particle diameter 40 ~ 60 μ m;
(3) the methanol solution wash-out that is 70 ~ 75% by concentration, elution flow rate is 0.5 ~ 5ml/min, substep is collected;
(4) elutriant of substep being collected respectively concentrating under reduced pressure, except desolventizing, obtains respectively capsicine and Dihydrocapsaicin crude product;
(5) by dissolving crude product in dehydrated alcohol, carry out recrystallization, filter dry capsicine of monomer and the monomer Dihydrocapsaicin crystal of obtaining.
2. the method for preparing capsicine and Dihydrocapsaicin monomer according to claim 1, is characterized in that: described ODS reverse-phase chromatographic column is reusable after Mathanol regenerating.
3. the method for preparing capsicine and Dihydrocapsaicin monomer according to claim 1, is characterized in that: in step (1), the purity of described capsaicine is more than 70%.
4. the method for preparing capsicine and Dihydrocapsaicin monomer according to claim 1, is characterized in that: in step (4), the vacuum tightness of concentrating under reduced pressure is 0.1Mpa, and temperature is 35 ~ 55 ℃.
5. the method for preparing capsicine and Dihydrocapsaicin monomer according to claim 1, is characterized in that: in step (5), the temperature of recrystallization is 4 ℃, and crystallization time is 9h.
6. the method for preparing capsicine and Dihydrocapsaicin monomer according to claim 2, is characterized in that: the consumption of the solvent methanol of described reverse-phase chromatography column regeneration is 2 ~ 4BV.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104030935B (en) * | 2014-06-25 | 2015-12-30 | 齐鲁工业大学 | A kind of method of reversed-phase resin purifying capsaicin monomer |
| CN104529806B (en) * | 2014-12-25 | 2017-04-19 | 承德天原药业股份有限公司 | Method for preparing high-purity capsaicin |
| CN111187177A (en) * | 2020-01-03 | 2020-05-22 | 海山都(上海)生物技术有限公司 | Method for preparing high-purity natural capsaicin monomer |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5955631A (en) * | 1997-07-18 | 1999-09-21 | Alps Pharmaceutical Ind. Co., Ltd. | Method for industrial purification of capsaicin |
| CN101260065A (en) * | 2008-04-11 | 2008-09-10 | 浙江大学宁波理工学院 | Method for separating high-pure capsicine monomer from capsicines compounds |
| CN101619028A (en) * | 2009-06-17 | 2010-01-06 | 张鹏 | Method for preparing capsicine monomer |
| CN102020580A (en) * | 2010-11-18 | 2011-04-20 | 湖南农业大学 | Method for low-pressure silica gel column chromatographic separation of capsaicin and dihydrocapsaicin |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5955631A (en) * | 1997-07-18 | 1999-09-21 | Alps Pharmaceutical Ind. Co., Ltd. | Method for industrial purification of capsaicin |
| EP0891966B1 (en) * | 1997-07-18 | 2003-04-16 | Alps Pharmaceutical Ind. Co. Ltd. | Method for industrial purification of capsaicin |
| CN101260065A (en) * | 2008-04-11 | 2008-09-10 | 浙江大学宁波理工学院 | Method for separating high-pure capsicine monomer from capsicines compounds |
| CN101619028A (en) * | 2009-06-17 | 2010-01-06 | 张鹏 | Method for preparing capsicine monomer |
| CN102020580A (en) * | 2010-11-18 | 2011-04-20 | 湖南农业大学 | Method for low-pressure silica gel column chromatographic separation of capsaicin and dihydrocapsaicin |
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Address after: 250000 Science Park, West New Town University, Ji'nan, Shandong Patentee after: Qilu University of Technology Address before: 250353 College of food science and biotechnology, College of science and technology, West Metro University, Shandong, Ji'nan Patentee before: Shandong Institute of Light Industry |
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