CN102649771A - Method of preparing capsaicine - Google Patents

Method of preparing capsaicine Download PDF

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Publication number
CN102649771A
CN102649771A CN2011100456364A CN201110045636A CN102649771A CN 102649771 A CN102649771 A CN 102649771A CN 2011100456364 A CN2011100456364 A CN 2011100456364A CN 201110045636 A CN201110045636 A CN 201110045636A CN 102649771 A CN102649771 A CN 102649771A
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ethyl acetate
column chromatography
oily matter
mixture
extract
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CN102649771B (en
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姜永涛
白景
李菊
阮征
于娟
徐光�
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Nanjing Lvye Pharma Co Ltd
Shandong Luye Pharmaceutical Co Ltd
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Shandong Luye Pharmaceutical Co Ltd
Nanjing Luye Pharmaceutical Co Ltd
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Abstract

The invention provides a preparing method for capsaicine, which comprises the following steps: chilli extract is sequentially subjected to extraction, column chromatography, crystallization and filtration; and the column chromatography is the polyamide column chromatography, and an obtained column chromatography oily substance is dissolved in one of solutions, such as the mixture of cyclohexane and vinegar naphtha, the mixture of normal hexane and the vinegar naphtha , the mixture of the normal heptane and the vinegar naphtha, the mixture of ligarine and the vinegar naphtha, acetone or alcohol, and then is subjected to crystallization and filtration, thereby obtaining the capsaicine crystal.

Description

A kind of preparation method of capsicine
Technical field
The present invention relates to a kind of preparation method of capsicine.
Background technology
Capsicine is the staple in the capsicum pungent component, and highly purified capsicine has many physiologically actives, can be used for medicine, like analgesia, treatment tetter and sacroiliitis etc.; Can be used for biochemical pesticide, effectively expel aphid, defoliator etc.; Also can be used for diet food.In addition, capsicine also can be used to produce functional coating, and the surface that is applied to cable and timber prevents biting of mouse, also can be used for making the raw material of tear bombnoun and defensive weapon.Because capsicine has purposes so widely, the research of its preparation method is also more and more received people's attention.
At present, the method for preparing capsicine mainly contains solvent extration, molecular distillation method, ion exchange method, column chromatography and macroreticular resin absorbing method etc.Though adopt aforesaid method can prepare the capsicine of certain purity, all used a large amount of organic solvents, and industrial equipments and production environment have been had relatively high expectations, realize that the suitability for industrialized production difficulty is big, manufacturing cost is high.
Chinese patent ZL 200710013364.3 provides a kind of preparation method who prepares high-purity capsaicin.It is a raw material with low peppery degree chilli extract, through extraction, alumina column chromatography, crystallization and the centrifugal high-purity capsaicin that extracts.But there are two aspect defectives in this preparation method:
(1) the extraction process complicacy is loaded down with trivial details, and adopts aluminum oxide to carry out column chromatography can to produce remarkable adsorption to capsicine, cause the capsicine loss;
(2) in crystallisation process, use ether, sherwood oil reagent; Simultaneously crystallized product is carried out centrifugal treating; Adopt that this kind method is as easy as rolling off a log blasts in operating process, and the gasifying solvent of centrifugal generation can produce violent irritating smell, therefore very high to production environment and equipment requirements; Can pollute environment, be unfavorable for carrying out suitability for industrialized production.
The present invention is directed to above-mentioned defective, provide a kind of simple to operate, safe and reliable, be prone to industriallization and the high method for preparing capsicine of yield.
Summary of the invention
The invention provides a kind of is raw material prepares the capsicine of high purity high yield successively through extraction, column chromatography, crystallization and filtration method with the chilli extract.
The preparation method of capsicine provided by the invention does; With chilli extract extract successively, column chromatography, crystallization and filtration; It is characterized by: column chromatography adopts polyamide column; Gained column chromatography oily matter is dissolved in carries out crystallization in the mixed organic solvents, wherein mixed organic solvents is selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture.
Extraction process adopts ordinary method to get final product; Be preferably: chilli extract is dissolved in adds mixed alkali liquor in the ETHYLE ACETATE again and extract; Collect ethyl acetate layer, with after the sodium chloride solution washing ethyl acetate layer being concentrated, evaporate to dryness must extract oily matter; Wherein mixed alkali liquor is selected from a kind of in yellow soda ash and sodium chloride mixture, sodium hydroxide and sodium chloride mixture, sodium hydrogencarbonate and the sodium chloride mixture, wherein both weight ratios 5~10: 1 in the mixed alkali liquor.
Sodium-chlor in the mixed alkali liquor can be regulated ionic strength as a kind of water-soluble salt, prevents emulsification, promotes extracting and demixing, and is not limited to a kind of water-soluble salt of sodium-chlor.
In the column chromatography process; The oily matter that extraction is obtained is put into the chromatography column that polymeric amide is housed and is carried out chromatographic separation with 50%~85% dissolve with ethanol, carries out wash-out with 50%~85% ethanol; The elutriant of capsicine part is rich in collection, and concentrated evaporate to dryness gets column chromatography oily matter.Wherein 50%~85% ethanol refers to the alcoholic acid volume(tric)fraction.
The elutriant of capsicine part is rich in collection: through the inspection of silica gel thin-layer chromatography chromatogram, dip in the sample that takes a morsel with kapillary, point is on F254 silica gel thin-layer chromatography plate, and inspection under uv lamp stops to collect when beginning to collect the blackening disappearance from there being blackening to occur.
In the crystallisation process; Column chromatography oily matter is dissolved in mixed organic solvents; Then-10~-30 ℃ of following crystallizations 24~48 hours, mixed organic solvents is selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture.
Wherein the weight ratio of mixed organic solvents and column chromatography oily matter is 0.4~5: 1, and the mixed organic solvents of use is not only measured little, and safe; So not only practiced thrift cost; And less demanding to environment and equipment, operation helps carrying out suitability for industrialized production easily.Both volume ratios are 20: 80~50: 50 in the mixed organic solvents.
The preparation method of capsicine provided by the invention is preferably chilli extract is dissolved in and adds mixed alkali liquor in the ETHYLE ACETATE again and extract, and collects ethyl acetate layer, and with after the sodium chloride solution washing ethyl acetate layer being concentrated, evaporate to dryness must extract oily matter; To extract oily matter with 50%~85% dissolve with ethanol, and put into the chromatography column that polymeric amide is housed and carry out chromatographic separation, and carry out wash-out with 50%~85% ethanol, and collect the elutriant that is rich in the capsicine part, concentrated evaporate to dryness gets column chromatography oily matter; Column chromatography oily matter is dissolved in the mixed organic solvents; Wherein the weight ratio of mixed organic solvents and column chromatography oily matter is 0.4~5: 1; Then-10~-30 ℃ of following crystallizations 24~48 hours; Again crystallisate is filtered and promptly get capsicine; Wherein mixed alkali liquor is selected from a kind of in yellow soda ash and sodium chloride mixture, sodium hydroxide and sodium chloride mixture, sodium hydrogencarbonate and the sodium chloride mixture; Both weight ratios 5~10: 1 in the mixed alkali liquor, mixed organic solvents are selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture, and both volume ratios are 20: 80~50: 50 in the mixed organic solvents.
The content of the capsicine of method gained produced according to the present invention is greater than 90%, and the rate of transform is greater than 60%.The calculation formula of the rate of transform of capsicine is among the present invention:
Figure BSA00000439720500031
The present invention prepares highly purified capsicine through extraction, column chromatography, crystallization and filtration.Extraction process is simple; And a large amount of experiment of process is groped; Find that polyamide column has good specificity to capsicine, it does not adsorb capsicine but can the active adsorption pigment, has not only reduced the loss of capsicine in leaching process; And the pigment in the chilli extract had the good adsorption effect, remove pigment effectively; Crystallisation process is selected specific organic solvent for use, and not only consumption is little, has practiced thrift cost, and not high to equipment requirements, simple to operate, safe and reliable, and environmentally safe is very suitable for industrialized production.
Embodiment
The present invention further sets forth the present invention through following examples, but is not limited in this.
Embodiment 1:
Take by weighing chilli extract 0.3kg and change separating funnel over to; Add ETHYLE ACETATE 1.5L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 1.5L purified water with 75g yellow soda ash and 15g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 50% dissolve with ethanol, and eluent is 50% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 0.4 times of weight part of use column chromatography oily matter, volume ratio are normal hexane-acetic acid ethyl dissolution of 20: 80, changes-10 ℃ of refrigerators over to and places 24 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 94.9%, the capsicine rate of transform 61.7%.
Embodiment 2:
Take by weighing chilli extract 0.5kg and change separating funnel over to; Add ETHYLE ACETATE 2.5L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 2.5L purified water with 125g yellow soda ash and 25g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 60% dissolve with ethanol, and eluent is 60% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 0.4 times of weight part of use column chromatography oily matter, volume ratio are normal hexane-acetic acid ethyl dissolution of 30: 70, changes-12 ℃ of refrigerators over to and places 24 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 93.5%, the capsicine rate of transform 62.3%.
Embodiment 3:
Take by weighing chilli extract 1kg and change the multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 5L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 5L purified water with 300g yellow soda ash and 50g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 60% dissolve with ethanol, and eluent is 60% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 1 times of weight part of use column chromatography oily matter, volume ratio are normal hexane-acetic acid ethyl dissolution of 40: 60, changes-15 ℃ of refrigerators over to and places 30 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 95.2%, the capsicine rate of transform 63%.
Embodiment 4:
Take by weighing chilli extract 1kg and change 30L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 5L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 5L purified water with 400g yellow soda ash and 50g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 75% dissolve with ethanol, and eluent is 75% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 2 times of weight parts of use column chromatography oily matter, volume ratio are normal heptane-acetic acid ethyl dissolution of 50: 50, changes-18 ℃ of refrigerators over to and places 36 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 93.0%, the capsicine rate of transform 62%.
Embodiment 5:
Take by weighing chilli extract 1kg and change 30L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 5L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 5L purified water with 250g sodium hydroxide and 50g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 85% dissolve with ethanol, and eluent is 85% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 1.5 times of weight parts of use column chromatography oily matter, volume ratio are normal heptane-acetic acid ethyl dissolution of 40: 60, changes-20 ℃ of refrigerators over to and places 40 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 94.8%, the capsicine rate of transform 61%.
Embodiment 6:
Take by weighing chilli extract 2kg and change 30L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 10L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 10L purified water with 1000g sodium hydrogencarbonate and 100g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 70% dissolve with ethanol, and eluent is 70% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 3 times of weight parts of use column chromatography oily matter, volume ratio are hexanaphthene-acetic acid ethyl dissolution of 20: 80, changes-25 ℃ of refrigerators after the dissolving over to and places 30 hours, and suction filtration promptly gets the needle crystal product.Detect capsicine content 95.6%, the capsicine rate of transform 60.5% through HPLC.
Embodiment 7:
Take by weighing chilli extract 2kg and change 30L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 10L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 10L purified water with 500g sodium hydroxide and 100g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 60% dissolve with ethanol, and eluent is 60% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and use column chromatography oily matter quality 0.8 times of amount, volume ratio are hexanaphthene-acetic acid ethyl dissolution of 30: 70, changes-25 ℃ of refrigerators over to and places 36 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 97.6%, the capsicine rate of transform 71%.
Embodiment 8:
Take by weighing chilli extract 2kg and change 30L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 10L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 10L purified water with 500g yellow soda ash and 100g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 75% dissolve with ethanol, and eluent is 75% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 4 times of weight parts of use column chromatography oily matter, volume ratio are 50: 50 petroleum ether-ethyl acetate dissolving, change-28 ℃ of refrigerators over to and place 26 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 90.1%, the capsicine rate of transform 60.7%.
Embodiment 9:
Take by weighing chilli extract 4kg and change 50L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 20L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 20L purified water with 1200g sodium hydrogencarbonate and 200g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 70% dissolve with ethanol, and eluent is 70% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 5 times of weight parts of use column chromatography oily matter, volume ratio are 35: 65 petroleum ether-ethyl acetate dissolving, change-30 ℃ of refrigerators over to and place 36 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 91.7%, the capsicine rate of transform 60.2%.
Embodiment 10:
Take by weighing chilli extract 4kg and change 50L multifunctional glass reaction kettle over to; Add ETHYLE ACETATE 20L and make its dissolving, join the mixed alkali liquor that dissolving makes in the 20L purified water with 1000g yellow soda ash and 200g sodium-chlor and extract, left standstill 12 hours; Ethyl acetate layer is concentrated, and evaporate to dryness must extract oily matter.
Extraction oily matter is crossed polyamide column chromatography after with 80% dissolve with ethanol, and eluent is 80% ethanol, collects the elutriant that is rich in the capsicine part, and concentrated, evaporate to dryness gets column chromatography oily matter.
Column chromatography oily matter is weighed, and 3 times of weight parts of use column chromatography oily matter, volume ratio are 25: 75 petroleum ether-ethyl acetate dissolving, change-30 ℃ of refrigerators over to and place 24 hours, and suction filtration promptly gets the needle crystal product.Detecting capsicine content through HPLC is 95.1%, the capsicine rate of transform 65%.

Claims (8)

1. the preparation method of a capsicine; With chilli extract extract successively, column chromatography, crystallization and filtration; It is characterized by: column chromatography adopts polyamide column; Gained column chromatography oily matter is dissolved in carries out crystallization in the mixed organic solvents, wherein mixed organic solvents is selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture.
2. preparation method according to claim 1; It is characterized by: extraction process adds mixed alkali liquor again and extracts for chilli extract is dissolved in the ETHYLE ACETATE; Collect ethyl acetate layer; With after the sodium chloride solution washing ethyl acetate layer being concentrated, evaporate to dryness must extract oily matter, and wherein mixed alkali liquor is selected from a kind of in yellow soda ash and sodium chloride mixture, sodium hydroxide and sodium chloride mixture, sodium hydrogencarbonate and the sodium chloride mixture.
3. preparation method according to claim 2 is characterized by both weight ratios 5~10: 1 in the mixed alkali liquor.
4. according to claim 2 or 3 described preparing methods; It is characterized by: the column chromatography process for oily matter that extraction is obtained with 50%~85% dissolve with ethanol; Put into the chromatography column that polymeric amide is housed and carry out chromatographic separation; Carry out wash-out with 50%~85% ethanol, collect the elutriant that is rich in the capsicine part, concentrated evaporate to dryness gets column chromatography oily matter.
5. preparation method according to claim 4; It is characterized by: crystallisation process is for to be dissolved in mixed organic solvents with column chromatography oily matter; Then-10~-30 ℃ of following crystallizations 24~48 hours, wherein mixed organic solvents is selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture.
6. preparation method according to claim 5, the weight ratio that it is characterized by mixed organic solvents and column chromatography oily matter is 0.4~5: 1.
7. preparation method according to claim 6 is characterized by in the mixed organic solvents both volume ratios 20: 80~50: 50.
8. according to the arbitrary described preparation method of claim 5~7; It is characterized by: chilli extract is dissolved in adds mixed alkali liquor in the ETHYLE ACETATE again and extract; Collect ethyl acetate layer, with after the sodium chloride solution washing ethyl acetate layer being concentrated, evaporate to dryness must extract oily matter; To extract oily matter with 50%~85% dissolve with ethanol, and put into the chromatography column that polymeric amide is housed and carry out chromatographic separation, and carry out wash-out with 50%~85% ethanol, and collect the elutriant that is rich in the capsicine part, concentrated evaporate to dryness gets column chromatography oily matter; Column chromatography oily matter is dissolved in the mixed organic solvents; Wherein the weight ratio of mixed organic solvents and column chromatography oily matter is 0.4~5: 1; Then-10~-30 ℃ of following crystallizations 24~48 hours; Again crystallisate is filtered and promptly get capsicine; Wherein mixed alkali liquor is selected from a kind of in yellow soda ash and sodium chloride mixture, sodium hydroxide and sodium chloride mixture, sodium hydrogencarbonate and the sodium chloride mixture; Both weight ratios are 5~10: 1 in the mixed alkali liquor, and mixed organic solvents is selected from a kind of in hexanaphthene and ethyl acetate mixture, normal hexane and ethyl acetate mixture, normal heptane and ethyl acetate mixture, sherwood oil and the ethyl acetate mixture, and both volume ratios are 20: 80~50: 50 in the mixed organic solvents.
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103726116A (en) * 2014-01-05 2014-04-16 赵晓冬 Functional fiber with auxiliary therapy effect
CN104187536A (en) * 2014-07-29 2014-12-10 中国农业科学院农产品加工研究所 Method for extracting and purifying capsaicin compound from chilli extract

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1153771A (en) * 1995-11-24 1997-07-09 厦门大学 Prodn of medicinal crystalline capsaicine
CN101020648A (en) * 2007-03-12 2007-08-22 青岛大学 Prepn process of high purity capcaicin
CN101250130A (en) * 2008-04-07 2008-08-27 广西大学 Method for purifying capsaicin compounds by ionic exchange fibre technology

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1153771A (en) * 1995-11-24 1997-07-09 厦门大学 Prodn of medicinal crystalline capsaicine
CN101020648A (en) * 2007-03-12 2007-08-22 青岛大学 Prepn process of high purity capcaicin
CN101250130A (en) * 2008-04-07 2008-08-27 广西大学 Method for purifying capsaicin compounds by ionic exchange fibre technology

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103726116A (en) * 2014-01-05 2014-04-16 赵晓冬 Functional fiber with auxiliary therapy effect
CN104187536A (en) * 2014-07-29 2014-12-10 中国农业科学院农产品加工研究所 Method for extracting and purifying capsaicin compound from chilli extract

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