CN1171857C - Process for enriching and purifying capsaicin with macroporous adsorption resin - Google Patents
Process for enriching and purifying capsaicin with macroporous adsorption resin Download PDFInfo
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- CN1171857C CN1171857C CNB021343845A CN02134384A CN1171857C CN 1171857 C CN1171857 C CN 1171857C CN B021343845 A CNB021343845 A CN B021343845A CN 02134384 A CN02134384 A CN 02134384A CN 1171857 C CN1171857 C CN 1171857C
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- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 title claims abstract description 93
- 239000011347 resin Substances 0.000 title claims abstract description 34
- 229920005989 resin Polymers 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 27
- 229960002504 capsaicin Drugs 0.000 title claims abstract description 12
- 235000017663 capsaicin Nutrition 0.000 title claims abstract description 12
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 9
- 239000000284 extract Substances 0.000 claims abstract description 43
- VQEONGKQWIFHMN-UHFFFAOYSA-N Nordihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O VQEONGKQWIFHMN-UHFFFAOYSA-N 0.000 claims abstract description 24
- XJQPQKLURWNAAH-UHFFFAOYSA-N dihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O XJQPQKLURWNAAH-UHFFFAOYSA-N 0.000 claims abstract description 24
- RBCYRZPENADQGZ-UHFFFAOYSA-N dihydrocapsaicin Natural products COC1=CC(COC(=O)CCCCCCC(C)C)=CC=C1O RBCYRZPENADQGZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003960 organic solvent Substances 0.000 claims abstract description 15
- 235000013399 edible fruits Nutrition 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 32
- 239000003463 adsorbent Substances 0.000 claims description 29
- 238000002425 crystallisation Methods 0.000 claims description 28
- 230000008025 crystallization Effects 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 17
- 239000003495 polar organic solvent Substances 0.000 claims description 16
- 235000002566 Capsicum Nutrition 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 238000001953 recrystallisation Methods 0.000 claims description 11
- 239000006002 Pepper Substances 0.000 claims description 7
- 241000722363 Piper Species 0.000 claims description 7
- 235000016761 Piper aduncum Nutrition 0.000 claims description 7
- 235000017804 Piper guineense Nutrition 0.000 claims description 7
- 235000008184 Piper nigrum Nutrition 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000012046 mixed solvent Substances 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 abstract description 11
- 240000008574 Capsicum frutescens Species 0.000 abstract description 10
- 239000013078 crystal Substances 0.000 abstract 3
- 235000002568 Capsicum frutescens Nutrition 0.000 abstract 2
- 239000004615 ingredient Substances 0.000 abstract 1
- 238000004811 liquid chromatography Methods 0.000 abstract 1
- 229960004756 ethanol Drugs 0.000 description 22
- 238000011010 flushing procedure Methods 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 238000005303 weighing Methods 0.000 description 10
- 239000001390 capsicum minimum Substances 0.000 description 7
- 240000004160 Capsicum annuum Species 0.000 description 6
- 235000019617 piquancy Nutrition 0.000 description 6
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 5
- 235000007862 Capsicum baccatum Nutrition 0.000 description 5
- 239000001728 capsicum frutescens Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- AKDLSISGGARWFP-UHFFFAOYSA-N Homodihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCCC(C)C)=CC=C1O AKDLSISGGARWFP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000009499 Vanilla fragrans Nutrition 0.000 description 1
- 244000263375 Vanilla tahitensis Species 0.000 description 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- -1 amide alkaloid Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001139 anti-pruritic effect Effects 0.000 description 1
- 239000003908 antipruritic agent Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000028016 temperature homeostasis Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a method for extracting an extract product which contains capsaicin from fruit or fruit peels of hot peppers and for preparing natural capsaicin crystals. Pungent ingredients in fruit or fruit peels of hot peppers are extracted by organic solvent. Extracting solution is concentrated in a pressure reducing mode, concentrates are separated and purified by macroporous adsorption resin, and an extract product which contains capsaicin is obtained. The content of the extract product is measured by a high efficiency liquid chromatography, and the total content of the capsaicin and dihydrocapsaicin in the obtained extract product can reach more than 33 %. After the extract product is continuously purified by macroporous adsorption resin, the extract product is recrystallized, and natural capsaicin crystals can be obtained. The total content of the capsaicin, the dihydrocapsaicin and nordihydrocapsaicin in the crystal can reach more than 97 %.
Description
Technical field
The present invention relates to a kind of the extraction from pepper fruit or pericarp with the macroporous adsorbent resin method contains capsicine (Capsaicin) extract and extract is carried out separation and purification prepares natural capsicine crystalline method.
Background technology
Macroporous adsorbent resin is the cross-linked polymer that a class does not contain ion-exchange group, and physico-chemical property is stable, is insoluble to acid, alkali and organic solvent, and organism is had concentrated, centrifugation and is not subjected to the interference of inorganic salts, strong ion and low molecular compound.Macroporous adsorbent resin by physical adsorption selectively adsorb organic compound matter reach the purpose of separate purifying.According to the surface properties of resin, can be divided into nonpolar, Semi-polarity and polarity three classes.
China be the earliest with capsicum as one of country of medicine, diseases such as traditional Chinese medical science capsicum treatment stomach cold commonly used and rheumatism.Piquancy components such as the capsicine in the capsicum have multiple physiologically active; as the sensory nervous system that some contained the P-material, cardiovascular, thermoregulation, stomach and intestine function remarkably influenced is arranged; have effects such as anti-inflammatory analgetic is antipruritic, promotion metabolism of fat, protection stomach and intestine, wherein comparatively outstanding is its unique long-acting analgesic effect.Therefore, the piquancy component in the capsicum has higher using value aspect medical health care.
Capsicine (Capsaicin) is the pungent vanilla amide alkaloid of a kind of extreme that proposes from solanaceae plant pepper (Capsicum annuum L.) or XIAOMIJIAO (C.frutescens L.) fruit.It is the main chemical compositions that has pharmic function in the capsicum.Piquancy component in the capsicum also comprises the analogue of capsicine, as Dihydrocapsaicin, Nordihydrocapsaicin, Homodihydrocapsaicin I, homocpsaicin etc.Pungency component in capsicum capsicine substantially accounts for 69%, and Dihydrocapsaicin accounts for 22%, Nordihydrocapsaicin 7%, Homodihydrocapsaicin I 1%, homocpsaicin 1%.
The chemical structural formula of capsicine, Dihydrocapsaicin is as follows:
The capsicine Dihydrocapsaicin
The method of existing separation and purification about capsicine can be divided three classes substantially: solvent extration, supercritical fluid extraction, column chromatography.Extract or capsicine crystalline that the present acquisition of extraction process with an organic solvent contains capsicine are more, but all need to use multiple inflammable and explosive organic solvent, industrial equipments is required height, complicated operating process, weak points such as product yield is not high, and waste liquid exhaust emission environment is serious.The weak point of supercritical fluid extraction is a plant and instrument cost height, and energy consumption is serious.The main drawback of column chromatography is that silica gel can not be regenerated, the production cost height.
Summary of the invention
The purpose of this invention is to provide a kind of from pepper fruit or pericarp, extract to contain capsicine (Capsaicin) extract and extract is carried out further separation and purification prepare natural capsicine crystalline method.The present invention adopts the macroporous adsorbent resin method, has easy and simple to handle, with low cost, the high advantages of piquancy component extraction yield such as yield is high, capsicine.Gained contains the total content of capsicine and Dihydrocapsaicin in the capsicine extract greater than 33%, and capsicine, Dihydrocapsaicin and Nordihydrocapsaicin total content are greater than 97% in the crystallization of gained capsicine.
The concrete steps of the inventive method are:
(1) dried powder of pepper fruit or pericarp is doubly measured (V/W) organic solvent with 4-6, also constantly extracts 1-2 hour under the stirring at 30-60 ℃, repeats to extract 2-3 time, and united extraction liquid concentrating under reduced pressure reclaims solvent and gets enriched material; Here said organic solvent is conventional organic solvent (normally 〉=ethanol or the methanol aqueous solution of 50%V/V, perhaps acetone or ethyl acetate);
(2) the gained enriched material is doubly measured 95% ethanol (V/V) dissolving of (V/W) with 2-4 after, mixes with polymeric adsorbent, add the water that is no less than 10 times of 95% ethanol volumes in addition, upper prop behind the stirring 2-3h; The dry weight of used polymeric adsorbent is the 1/10-1/8 of dry pepper fruit or pericarp weight; Said polymeric adsorbent is nonpolar or low polar macroporous adsorbent resin (can be HPD series macroporous adsorbent resin 100,130,200 or 300 models, or other the nonpolar or low polar macroporous adsorption resin of working as with its polar phase);
(3) with big water gaging wash to elutant be colourless after, use polar organic solvent wash-out capsicine instead; Used eluting solvent volume is a 2-4 times of column volume, and the elutriant flow is 0.5-1 times of column volume/h; Said polar organic solvent is that concentration is the ethanol or the methanol aqueous solution of 〉=85% (V/V), or acetone, or ethyl acetate;
(4) the polar organic solvent elutriant is reclaimed solvent through concentrating under reduced pressure, promptly get the required capsicine extract that contains; Extract is red oily liquids, and extremely pungent smell is arranged; Wherein the total content of capsicine and Dihydrocapsaicin is not less than 33%;
(5) with above-mentioned contain the capsicine extract and doubly measure 95% (V/V) aqueous ethanolic solution dissolving of (V/W) with 2-4 after, mixes with polymeric adsorbent, add 10 times the water that is no less than 95% ethanol volume in addition, upper prop behind the stirring 2-3h; The dry weight of used polymeric adsorbent be contain the capsicine extract weight 8-10 doubly; Said polymeric adsorbent is polar macroporous adsorption resin (can be the macroporous adsorbent resin 500 or 600 models of HPD series, or other the polar macroporous adsorption resin of working as with its polar phase);
(6) with big water gaging wash to elutant be colourless after, use the non-polar organic solvent wash-out instead, used eluting solvent volume is a 2-4 times of column volume, the elutriant flow is 0.5-1 times of column volume/h; Said non-polar organic solvent is a sherwood oil, normal hexane, the mixed solvent of any two or three in hexanaphthene or this three kinds of solvents;
(7) with polar organic solvent wash-out capsicine, the volume of used eluting solvent is a 2-4 times of column volume, and the elutriant flow is 0.5-1 times of column volume/h; Said polar organic solvent is that concentration is the ethanol or the methanol aqueous solution of 〉=95% (V/V), or acetone, or ethyl acetate;
(8) polar organic solvent elutriant concentrating under reduced pressure is reclaimed solvent, gained enriched material recrystallization organic solvent dissolution, 25-60 ℃ of vibration 15-25min, leave standstill crystallization, with resulting crystallization recrystallization once more, promptly get the crystallization of snowy white leaflet sheet capsicine, wherein capsicine, Dihydrocapsaicin and Nordihydrocapsaicin total content are more than 97%; Said recrystallization organic solvent is a sherwood oil, ether, the mixed solvent of normal hexane or above-mentioned three kinds of solvents any two or three.
Compared with the prior art, the present invention has following major advantage:
(1) owing to select macroporous adsorbent resin for use, its adsorption selectivity to capsicine is good, and absorption is fast, and desorb is also fast, and loading capacity is bigger; The physical and chemical stability height, physical strength is good, and regeneration is easily; Operate very easyly, step is few, and is with low cost, and the piquancy component extraction rate reached is more than 95%, and all recyclable utilization of solvent also is applicable to large-scale commercial production.
(2) by the inventive method produce to contain in the capsicine extract piquancy component content higher, capsicine, Dihydrocapsaicin total content can reach more than 33%.The capsicine crystallization look of producing is snow-white, purity is high, and wherein capsicine, Dihydrocapsaicin and Nordihydrocapsaicin total content are more than 97%.
Embodiment
The invention will be further described below by specific embodiment.
Embodiment 1:
Take by weighing the dry pericarp powder of Changsha red pepper 200g, constantly stir down for 30 ℃ with 800ml acetone respectively and extract 3 times, each 1h filters, and merging filtrate concentrates and reclaims acetone.After enriched material dissolves with 30ml 95% ethanol (V/V), with dry weight be the HPD100 mixed with resin of 25g, other adds 400ml water, constant speed (30rpm) stirs 2h, the flushing of 1000ml water, flow is 400ml/h, uses 85% (V/V) ethanol 300ml flushing instead, and flow is 75ml/h, concentrate ethanol eluate, promptly obtain containing capsicine extract 1.86g, yield 0.93%, the HPLC method records Dihydrocapsaicin in the extract, the capsicine total content is 38.25%.
Embodiment 2:
Take by weighing the dry pericarp powder of red pepper 200g, constantly stir down for 60 ℃ with 1200ml 50% (V/V) ethanol respectively and extract 2 times, each 1h filters, and merging filtrate concentrates and reclaims ethanol.After enriched material dissolves with 40ml 95% ethanol (V/V), with dry weight be the HPD130 mixed with resin of 22.5g, other adds 400ml water, constant speed (30rpm) stirs 2h, the flushing of 1000ml water, flow is 400ml/h, uses 95% (V/V) ethanol 270ml flushing instead, and flow is 120ml/h, concentrate ethanol eluate, promptly obtain containing capsicine extract 1.78g, yield 0.89%, the HPLC method records Dihydrocapsaicin in the extract, the capsicine total content is 38.64%.
Embodiment 3:
Take by weighing the dry pericarp powder of red pepper 200g, constantly stir down for 60 ℃ with 5 times of weight, 80% ethanol respectively and extract 3 times, each 1h filters, and merging filtrate concentrates and reclaims ethanol.After enriched material dissolves with 40ml 95% ethanol (V/V), with dry weight be the HPD300 mixed with resin of 20g, other adds 400ml water, and constant speed (30rpm) stirs 3h, the flushing of 1000ml water, flow is 400ml/h, use methyl alcohol 120ml flushing instead, flow is 50ml/h, concentrates meoh eluate, promptly obtain containing capsicine extract 1.88g, yield 0.94%.The HPLC method records Dihydrocapsaicin in the extract, the capsicine total content is 37.35%.
Embodiment 4:
Take by weighing red pepper dry fruit powder 200g, constantly stir down for 50 ℃ with 800ml methyl alcohol and extract 3 times, each 1h filters, and merging filtrate concentrates and reclaims methyl alcohol.After enriched material dissolves with 40ml 95% ethanol (V/V), with dry weight be the HPD100 mixed with resin of 25g, other adds 500ml water, constant speed (30rpm) stirs 2h, the flushing of 1000ml water, flow is 400ml/h, uses ethyl acetate 300ml flushing instead, and flow is 75ml/h, concentrate eluent ethyl acetate liquid, promptly obtain containing capsicine extract 1.88g, yield 0.94%, the HPLC method records Dihydrocapsaicin in the extract, the capsicine total content is 36.14%.
Embodiment 5
Take by weighing red pepper dry fruit powder 200g, constantly stir down for 50 ℃ with the 1000ml ethyl acetate and extract 3 times, each 1h filters, and merging filtrate concentrates and reclaims ethyl acetate.After 95% ethanol (V/V) dissolving of enriched material with 30ml, with dry weight be the HPD100 mixed with resin of 25g, other adds 400ml water, constant speed (30rpm) stirs 2h, the flushing of 1000ml water, flow is 400ml/h, uses acetone 300ml flushing instead, and flow is 100ml/h, concentrate the acetone elutriant, promptly obtain containing capsicine extract 2.06g, yield 1.03%, the HPLC method records Dihydrocapsaicin in the extract, the capsicine total content is 34.75%.
Embodiment 6
Take by weighing and contain capsicine extract 3.00g in the foregoing description 1, after the dissolving of 6ml 95% (V/V) aqueous ethanolic solution, with dry weight be the HPD600 mixed with resin of 25g, other adds 100ml water, stirs upper prop behind the 2h.500ml water be flushed to elutant be colourless after, use 300ml sherwood oil wash-out instead, flow is 75ml/h.95% (V/V) ethanol 300ml continues wash-out, and flow is 75ml/h.The concentrating under reduced pressure ethanol eluate reclaims solvent, gained enriched material petroleum ether dissolution, 50 ℃ of 25min that vibrate leave standstill crystallization, with resulting crystallization recrystallization once more, get final product snowy white leaflet sheet capsicine crystallization 0.91g.The capsicine rate of recovery is 82.5%.The HPLC method records and contains Nordihydrocapsaicin 9.21% in the crystallization, Dihydrocapsaicin 28.54%, and capsicine 60.78%, three's total content are 98.53%.
Embodiment 7
Take by weighing and contain capsicine extract 3.00g in the foregoing description 2, after 95% (V/V) aqueous ethanolic solution dissolving with 9ml, with dry weight be the HPD500 mixed with resin of 30g, other adds 150ml water, stirs upper prop behind the 2h.500ml water be flushed to elutant be colourless after, use 270ml normal hexane wash-out instead, flow is 70ml/h.Dehydrated alcohol 350ml continues wash-out, and flow is 75ml/h.The concentrating under reduced pressure ethanol eluate reclaims solvent, gained enriched material ether dissolution, 30 ℃ of 20min that vibrate leave standstill crystallization, with resulting crystallization recrystallization once more, get final product snowy white leaflet sheet capsicine crystallization 0.92g.The capsicine rate of recovery is 83.4%.The HPLC method records and contains Nordihydrocapsaicin 9.18% in the crystallization, Dihydrocapsaicin 28.36%, and capsicine 60.27%, three's total content are 97.81%.
Embodiment 8
Take by weighing and contain capsicine extract 3.00g in the foregoing description 3, after the dissolving of 6ml 95% (V/V) aqueous ethanolic solution, with dry weight be the HPD500 mixed with resin of 25g, other adds 200ml water, stirs upper prop behind the 3h.500ml water be flushed to elutant be colourless after, use hexanaphthene 250ml wash-out instead, flow is 60ml/h.Methyl alcohol 300ml continues wash-out, and flow is 100ml/h.The concentrating under reduced pressure meoh eluate reclaims solvent, gained enriched material n-hexane dissolution, 40 ℃ of 25min that vibrate leave standstill crystallization, with resulting crystallization recrystallization once more, get final product snowy white leaflet sheet capsicine crystallization 0.90g.The capsicine rate of recovery is 81.3%.The HPLC method records and contains Nordihydrocapsaicin 9.19% in the crystallization, Dihydrocapsaicin 28.45%, and capsicine 60.76%, three's total content are 98.40%.
Embodiment 9
Take by weighing and contain capsicine extract 3.00g in the foregoing description 4, after 95% (V/V) aqueous ethanolic solution dissolving with 6ml, with dry weight be the HPD600 mixed with resin of 25g, other adds 200ml water, stirs upper prop behind the 2h.500ml water be flushed to elutant be colourless after, use sherwood oil instead: the mixed solvent 300ml wash-out of hexanaphthene=1: 1 (V/V), flow is 75ml/h.Acetone 300ml continues wash-out, and flow is 75ml/h.Concentrating under reduced pressure acetone elutriant reclaims solvent, gained enriched material sherwood oil: the mixed solvent dissolving of ether=1: 1 (V/V), 30 ℃ of vibration 25min leave standstill crystallization, with resulting crystallization recrystallization once more, get final product snowy white leaflet sheet capsicine crystallization 0.92g.The capsicine rate of recovery is 82.0%.The HPLC method records and contains Nordihydrocapsaicin 9.21% in the crystallization, Dihydrocapsaicin 28.52%, and capsicine 60.75%, three's total content are 98.48%.
Embodiment 10
Take by weighing and contain capsicine extract 3.00g in the foregoing description 5, after the dissolving of 6ml 95% (V/V) aqueous ethanolic solution, with dry weight be the HPD500 mixed with resin of 25g, other adds 200ml water, stirs upper prop behind the 2h.500ml water be flushed to elutant be colourless after, use 270ml sherwood oil wash-out instead, flow is 70ml/h.Ethyl acetate 300ml continues wash-out, and flow is 60ml/h.Concentrating under reduced pressure eluent ethyl acetate liquid reclaims solvent, gained enriched material sherwood oil: ether: the mixed solvent dissolving of hexanaphthene=1: 1: 1,30 ℃ of vibration 25min leave standstill crystallization, with resulting crystallization recrystallization once more, get final product snowy white leaflet sheet capsicine crystallization 0.89g.The capsicine rate of recovery is 81.0%.The HPLC method records and contains Nordihydrocapsaicin 9.16% in the crystallization, Dihydrocapsaicin 28.37%, and capsicine 60.43%, three's total content are 97.96%.
Claims (4)
1. method that adopts enrichment of macroporous adsorbent resin method and purifying capsaicin, concrete steps comprise:
(1) dried powder of pepper fruit or pericarp is doubly measured the V/W organic solvent with 4-6, also constantly extracted 1-2 hour under the stirring at 30-60 ℃, repeat to extract 2-3 time, united extraction liquid concentrating under reduced pressure reclaims solvent and gets enriched material; Here said organic solvent is conventional organic solvent;
(2) the gained enriched material is doubly measured the 95% ethanol V/V dissolving of V/W with 2-4 after, mixes with polymeric adsorbent, add the water that is no less than 10 times of 95% ethanol volumes in addition, upper prop behind the stirring 2-3h; The dry weight of used polymeric adsorbent is the 1/10-1/8 of dry pepper fruit or pericarp weight; Said polymeric adsorbent is nonpolar or low polar macroporous adsorbent resin;
(3) with big water gaging wash to elutant be colourless after, use polar organic solvent wash-out capsicine instead; Used eluting solvent volume is a 2-4 times of column volume, and the elutriant flow is 0.5-1 times of column volume/h; Said polar organic solvent is that concentration is 〉=ethanol or the methanol aqueous solution of 85%V/V, or acetone, or ethyl acetate;
(4) the polar organic solvent elutriant is reclaimed solvent through concentrating under reduced pressure, promptly get the required capsicine extract that contains; Extract is red oily liquids, and extremely pungent smell is arranged; Wherein the total content of capsicine and Dihydrocapsaicin is not less than 33%;
(5) after the extract that will contain capsicine is doubly measured the 95% aqueous ethanolic solution dissolving of V/W with 2-4, mixes, add 10 times the water that is no less than 95% ethanol volume in addition, upper prop behind the stirring 2-3h with polymeric adsorbent; The dry weight of used polymeric adsorbent be contain the capsicine extract weight 8-10 doubly; Said polymeric adsorbent is a polar macroporous adsorption resin;
(6) with big water gaging wash to elutant be colourless after, use the non-polar organic solvent wash-out instead, used eluting solvent volume is a 2-4 times of column volume, the elutriant flow is 0.5-1 times of column volume/h; Said non-polar organic solvent is a sherwood oil, normal hexane, and the mixed solvent of any two or three in hexanaphthene or this three kinds of solvents:
(7) with polar organic solvent wash-out capsicine, the volume of used eluting solvent is a 2-4 times of column volume, and the elutriant flow is 0.5-1 times of column volume/h; Said polar organic solvent is that concentration is 〉=95% ethanol or methanol aqueous solution, or acetone, or ethyl acetate;
(8) polar organic solvent elutriant concentrating under reduced pressure is reclaimed solvent, gained enriched material recrystallization organic solvent dissolution, 25-60 ℃ of vibration 15-25min, leave standstill crystallization, with resulting crystallization recrystallization once more, promptly get the crystallization of snowy white leaflet sheet capsicine, wherein capsicine, Dihydrocapsaicin and Nordihydrocapsaicin total content are more than 97%; Said recrystallization organic solvent is a sherwood oil, ether, the mixed solvent of normal hexane or these three kinds of solvents any two or three.
2. in accordance with the method for claim 1, it is characterized in that ethanol or the methanol aqueous solution of the said organic solvent of step (1), perhaps acetone or ethyl acetate for 〉=50%V/V.
3. according to claim 1 or 2 described methods, it is characterized in that the said macroporous adsorbent resin of step (2) is HPD series macroporous adsorbent resin 100,130,200 or 300 models, or other polar phase macroporous adsorbent resin of working as.
4. in accordance with the method for claim 1, it is characterized in that the said polymeric adsorbent of step (5) is the macroporous adsorbent resin 500 or 600 models of HPD series, or other polar phase macroporous adsorbent resin of working as.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB021343845A CN1171857C (en) | 2002-07-18 | 2002-07-18 | Process for enriching and purifying capsaicin with macroporous adsorption resin |
Applications Claiming Priority (1)
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| CNB021343845A CN1171857C (en) | 2002-07-18 | 2002-07-18 | Process for enriching and purifying capsaicin with macroporous adsorption resin |
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| CN1171857C true CN1171857C (en) | 2004-10-20 |
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Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101200433B (en) * | 2007-11-08 | 2010-04-07 | 山东省分析测试中心 | Method for preparing high-purity capsaicin monomer |
| CN101619028B (en) * | 2009-06-17 | 2012-06-27 | 张鹏 | Method for preparing capsicine monomer |
| CN101914033A (en) * | 2010-08-05 | 2010-12-15 | 杨红梅 | Method for extracting capsaicine crystals from chilli extracts |
| CN102020580B (en) * | 2010-11-18 | 2013-11-13 | 湖南农业大学 | Method for low-pressure silica gel column chromatographic separation of capsaicin and dihydrocapsaicin |
| CN102008595B (en) * | 2010-11-18 | 2013-03-20 | 湖南农业大学 | Method for separating capsaicinoids from chilli extract |
| 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 |
| CN108041521A (en) * | 2017-11-24 | 2018-05-18 | 安徽省林锦记食品工业有限公司 | A kind of processing method of the anti-choke jelly of hot phycoerythrobilin |
| CN109603201B (en) * | 2018-12-28 | 2021-07-16 | 晨光生物科技集团股份有限公司 | Method for removing benzoic acid from Capsici fructus extract |
| 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 |
| CN114805110A (en) * | 2022-04-26 | 2022-07-29 | 云南信达健康科技有限公司 | Preparation method of pepper extract |
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