CN101619028A - 一种制备辣椒碱单体的方法 - Google Patents
一种制备辣椒碱单体的方法 Download PDFInfo
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- CN101619028A CN101619028A CN200910148379A CN200910148379A CN101619028A CN 101619028 A CN101619028 A CN 101619028A CN 200910148379 A CN200910148379 A CN 200910148379A CN 200910148379 A CN200910148379 A CN 200910148379A CN 101619028 A CN101619028 A CN 101619028A
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- capsicine
- alcohol
- monomer
- dihydrocapsaicin
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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 127
- 239000000178 monomer Substances 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title claims abstract description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 94
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 235000002566 Capsicum Nutrition 0.000 claims abstract description 22
- 239000001390 capsicum minimum Substances 0.000 claims abstract description 20
- 239000012043 crude product Substances 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 239000000284 extract Substances 0.000 claims abstract 2
- VQEONGKQWIFHMN-UHFFFAOYSA-N Nordihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O VQEONGKQWIFHMN-UHFFFAOYSA-N 0.000 claims description 76
- 229960002504 capsaicin Drugs 0.000 claims description 46
- 239000007788 liquid Substances 0.000 claims description 40
- XJQPQKLURWNAAH-UHFFFAOYSA-N dihydrocapsaicin Chemical compound COC1=CC(CNC(=O)CCCCCCC(C)C)=CC=C1O XJQPQKLURWNAAH-UHFFFAOYSA-N 0.000 claims description 39
- RBCYRZPENADQGZ-UHFFFAOYSA-N dihydrocapsaicin Natural products COC1=CC(COC(=O)CCCCCCC(C)C)=CC=C1O RBCYRZPENADQGZ-UHFFFAOYSA-N 0.000 claims description 39
- 235000017663 capsaicin Nutrition 0.000 claims description 30
- 240000008574 Capsicum frutescens Species 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 239000003463 adsorbent Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 238000010521 absorption reaction Methods 0.000 claims description 13
- 238000000605 extraction Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- 230000008929 regeneration Effects 0.000 claims description 8
- 238000011069 regeneration method Methods 0.000 claims description 8
- 239000000049 pigment Substances 0.000 claims description 7
- 238000001953 recrystallisation Methods 0.000 claims description 7
- 238000011084 recovery Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- 229910001220 stainless steel Inorganic materials 0.000 claims description 4
- 239000010935 stainless steel Substances 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 230000001172 regenerating effect Effects 0.000 claims 1
- 230000003245 working effect Effects 0.000 claims 1
- 238000005516 engineering process Methods 0.000 abstract description 4
- 239000003960 organic solvent Substances 0.000 abstract description 4
- 241000208293 Capsicum Species 0.000 abstract 4
- 239000000341 volatile oil Substances 0.000 abstract 2
- 230000002745 absorbent Effects 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- 238000001179 sorption measurement Methods 0.000 description 8
- 239000006228 supernatant Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- -1 capsaicin compound Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000006002 Pepper Substances 0.000 description 2
- 241000722363 Piper Species 0.000 description 2
- 235000016761 Piper aduncum Nutrition 0.000 description 2
- 235000017804 Piper guineense Nutrition 0.000 description 2
- 235000008184 Piper nigrum Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- TZZAKSLHHIJRLL-UHFFFAOYSA-N 4-hydroxy-3-methoxybenzamide Chemical class COC1=CC(C(N)=O)=CC=C1O TZZAKSLHHIJRLL-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000004185 countercurrent chromatography Methods 0.000 description 1
- GPWDPLKISXZVIE-UHFFFAOYSA-N cyclo[18]carbon Chemical compound C1#CC#CC#CC#CC#CC#CC#CC#CC#C1 GPWDPLKISXZVIE-UHFFFAOYSA-N 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
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- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 235000019633 pungent taste Nutrition 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
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- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | 其他 | |
流出液A(%) | 5.17 | 1.49 | 90.25 | 3.09 |
流出液B(%) | 94.73 | 3.14 | 0.57 | 1.56 |
流出液C(%) | 7.54 | 91.49 | 0.13 | 0.84 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | |
1L辣椒精油(g) | 7.08 | 2.23 | 0.38 |
单体成品(g) | 6.45 | 1.98 | 0.33 |
纯度(%) | 99.20 | 98.71 | 98.05 |
收率(%) | 91.10 | 88.78 | 86.84 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | 其他 | |
流出液A(%) | 5.13 | 1.36 | 91.05 | 2.46 |
流出液B(%) | 95.78 | 3.02 | 0.39 | 0.81 |
流出液C(%) | 6.91 | 92.75 | 0.21 | 0.13 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 |
1Kg干红辣椒粉(g) | 7.57 | 2.64 | 1.02 |
单体成品(g) | 6.96 | 2.35 | 0.88 |
纯度(%) | 99.01 | 98.25 | 98.01 |
收率(%) | 91.94 | 89.01 | 86.27 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | 其他 | |
流出液A(%) | 5.19 | 1.07 | 91.12 | 2.62 |
流出液B(%) | 93.75 | 5.17 | 0.10 | 0.98 |
流出液C(%) | 6.01 | 91.50 | 0.02 | 2.47 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | |
100L辣椒精油(g) | 707.59. | 223.16 | 38.25 |
单体成品(g) | 625.32 | 192.50 | 33.28 |
纯度(%) | 98.53 | 98.21 | 98.35 |
收率(%) | 88.37 | 86.26 | 87.00 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | 其他 | |
流出液A(%) | 5.25 | 0.72 | 92.15 | 1.88 |
流出液B(%) | 94.12 | 5.13 | 0.27 | 0.48 |
流出液C(%) | 7.57 | 91.25 | 0.51 | 0.67 |
辣椒碱 | 二氢辣椒碱 | 降二氢辣椒碱 | |
100Kg干红辣椒粉(g) | 757.19 | 264.31 | 101.51 |
单体成品(g) | 688.50 | 225.00 | 87.30 |
纯度(%) | 98.52 | 98.00 | 98.27 |
收率(%) | 90.92 | 85.12 | 86.00 |
Claims (10)
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CN101619028A true CN101619028A (zh) | 2010-01-06 |
CN101619028B CN101619028B (zh) | 2012-06-27 |
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Cited By (14)
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CN102020580A (zh) * | 2010-11-18 | 2011-04-20 | 湖南农业大学 | 一种低压硅胶柱色谱分离辣椒素与二氢辣椒素的方法 |
CN102093243A (zh) * | 2010-09-29 | 2011-06-15 | 天津春发食品配料有限公司 | 一种制备降二氢辣椒素的方法 |
CN102432489A (zh) * | 2011-11-29 | 2012-05-02 | 山东轻工业学院 | 一种制备辣椒碱和二氢辣椒碱单体的方法 |
CN102617387A (zh) * | 2012-01-13 | 2012-08-01 | 浙江大学 | 一种从辣椒碱类化合物中分离辣椒碱单体的方法 |
CN102715482A (zh) * | 2012-06-19 | 2012-10-10 | 许秋雁 | 一种脱色水性辣椒精的生产方法 |
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CN102796020A (zh) * | 2011-05-25 | 2012-11-28 | 北京金水红生物科技研究院 | 从辣椒精生产辣椒素晶体的工艺 |
CN103254092A (zh) * | 2013-05-19 | 2013-08-21 | 常州亚当生物技术有限公司 | 辣椒碱生产工艺 |
CN103936612A (zh) * | 2014-04-28 | 2014-07-23 | 福建正味生物科技有限公司 | 一种辣椒碱类化合物的制备方法 |
CN104187536A (zh) * | 2014-07-29 | 2014-12-10 | 中国农业科学院农产品加工研究所 | 一种从辣椒精中提取纯化辣椒碱类化合物的方法 |
CN105331291A (zh) * | 2015-12-15 | 2016-02-17 | 云南宏绿辣素有限公司 | 一种提高辣椒油树脂中辣椒素单体比例的方法 |
CN105368323A (zh) * | 2015-12-15 | 2016-03-02 | 文山永润辣素有限公司 | 一种无色高辣素含量的辣椒油树脂的制备方法 |
CN111187177A (zh) * | 2020-01-03 | 2020-05-22 | 海山都(上海)生物技术有限公司 | 一种制备高纯度天然辣椒碱单体的方法 |
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2009
- 2009-06-17 CN CN200910148379XA patent/CN101619028B/zh not_active Expired - Fee Related
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CN111187177A (zh) * | 2020-01-03 | 2020-05-22 | 海山都(上海)生物技术有限公司 | 一种制备高纯度天然辣椒碱单体的方法 |
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