CN110437070A - 一种以甜菊叶为原料综合利用制备高纯度绿原酸的方法及其制备得到的绿原酸 - Google Patents
一种以甜菊叶为原料综合利用制备高纯度绿原酸的方法及其制备得到的绿原酸 Download PDFInfo
- Publication number
- CN110437070A CN110437070A CN201910775660.XA CN201910775660A CN110437070A CN 110437070 A CN110437070 A CN 110437070A CN 201910775660 A CN201910775660 A CN 201910775660A CN 110437070 A CN110437070 A CN 110437070A
- Authority
- CN
- China
- Prior art keywords
- chlorogenic acid
- alcohol
- stevia rebaudian
- rebaudian leaf
- raw material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 235000001368 chlorogenic acid Nutrition 0.000 title claims abstract description 86
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 title claims abstract description 85
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 title claims abstract description 85
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 title claims abstract description 85
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 title claims abstract description 85
- 229940074393 chlorogenic acid Drugs 0.000 title claims abstract description 85
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 title claims abstract description 85
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 title claims abstract description 85
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 30
- 239000002994 raw material Substances 0.000 title claims abstract description 25
- 244000228451 Stevia rebaudiana Species 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 95
- 241000544066 Stevia Species 0.000 claims abstract description 62
- 239000004952 Polyamide Substances 0.000 claims abstract description 27
- 229920002647 polyamide Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 24
- 229920005989 resin Polymers 0.000 claims abstract description 24
- 239000000284 extract Substances 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 14
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 11
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 238000001953 recrystallisation Methods 0.000 claims abstract description 11
- 238000011068 loading method Methods 0.000 claims abstract description 10
- 238000001179 sorption measurement Methods 0.000 claims abstract description 9
- 239000012065 filter cake Substances 0.000 claims abstract description 6
- 235000019441 ethanol Nutrition 0.000 claims description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 15
- 235000013824 polyphenols Nutrition 0.000 claims description 15
- 239000004383 Steviol glycoside Substances 0.000 claims description 12
- 235000019411 steviol glycoside Nutrition 0.000 claims description 12
- 229930182488 steviol glycoside Natural products 0.000 claims description 12
- 150000008144 steviol glycosides Chemical class 0.000 claims description 12
- 235000019202 steviosides Nutrition 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 5
- 238000001694 spray drying Methods 0.000 claims description 3
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 229920006122 polyamide resin Polymers 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims 1
- 238000000967 suction filtration Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 238000011084 recovery Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 40
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- 238000010828 elution Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 5
- 244000269722 Thea sinensis Species 0.000 description 4
- 235000009508 confectionery Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 241000219226 Acer truncatum Species 0.000 description 3
- 241000723353 Chrysanthemum Species 0.000 description 3
- 235000007516 Chrysanthemum Nutrition 0.000 description 3
- 241000533293 Sesbania emerus Species 0.000 description 3
- DQFAAIWCCHDCLO-UHFFFAOYSA-N acetonitrile;formic acid;hydrate Chemical compound O.CC#N.OC=O DQFAAIWCCHDCLO-UHFFFAOYSA-N 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000205585 Aquilegia canadensis Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- AAWZDTNXLSGCEK-WYWMIBKRSA-N (-)-quinic acid Chemical compound O[C@@H]1C[C@](O)(C(O)=O)C[C@@H](O)[C@H]1O AAWZDTNXLSGCEK-WYWMIBKRSA-N 0.000 description 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000206601 Carnobacterium mobile Species 0.000 description 1
- 241000208688 Eucommia Species 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- SOWVWGZSLABJMC-UHFFFAOYSA-N hexahydrogallic acid Natural products OC1CC(C(O)=O)CC(O)C1O SOWVWGZSLABJMC-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229930015704 phenylpropanoid Natural products 0.000 description 1
- 125000001474 phenylpropanoid group Chemical group 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seasonings (AREA)
Abstract
Description
时间/min | 流动相A% | 流动相B% |
0-20 | 0 | 100 |
20-35 | 100 | 0 |
35-37 | 100→0 | 0→100 |
37-45 | 0 | 100 |
Claims (10)
Priority Applications (1)
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CN201910775660.XA CN110437070B (zh) | 2019-08-21 | 2019-08-21 | 一种以甜菊叶为原料综合利用制备绿原酸的方法及其制备得到的绿原酸 |
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CN201910775660.XA CN110437070B (zh) | 2019-08-21 | 2019-08-21 | 一种以甜菊叶为原料综合利用制备绿原酸的方法及其制备得到的绿原酸 |
Publications (2)
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CN110437070A true CN110437070A (zh) | 2019-11-12 |
CN110437070B CN110437070B (zh) | 2022-04-15 |
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CN201910775660.XA Active CN110437070B (zh) | 2019-08-21 | 2019-08-21 | 一种以甜菊叶为原料综合利用制备绿原酸的方法及其制备得到的绿原酸 |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN118063319A (zh) * | 2024-04-17 | 2024-05-24 | 诸城市浩天生物科技有限公司 | 一种利用甜叶菊提取液制备高纯绿原酸的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102924544A (zh) * | 2012-10-30 | 2013-02-13 | 晨光生物科技集团股份有限公司 | 从甜菊叶中分步制备甜菊糖和绿原酸的方法 |
CN109265346A (zh) * | 2018-09-30 | 2019-01-25 | 晨光生物科技集团股份有限公司 | 一种甜叶菊的工业化利用方法及其绿原酸和甜菊糖苷 |
CN109432153A (zh) * | 2018-10-25 | 2019-03-08 | 东台市浩瑞生物科技有限公司 | 一种用复合壳聚糖絮凝法制备甜菊多酚的方法 |
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2019
- 2019-08-21 CN CN201910775660.XA patent/CN110437070B/zh active Active
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102924544A (zh) * | 2012-10-30 | 2013-02-13 | 晨光生物科技集团股份有限公司 | 从甜菊叶中分步制备甜菊糖和绿原酸的方法 |
CN109265346A (zh) * | 2018-09-30 | 2019-01-25 | 晨光生物科技集团股份有限公司 | 一种甜叶菊的工业化利用方法及其绿原酸和甜菊糖苷 |
CN109432153A (zh) * | 2018-10-25 | 2019-03-08 | 东台市浩瑞生物科技有限公司 | 一种用复合壳聚糖絮凝法制备甜菊多酚的方法 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN118063319A (zh) * | 2024-04-17 | 2024-05-24 | 诸城市浩天生物科技有限公司 | 一种利用甜叶菊提取液制备高纯绿原酸的方法 |
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Denomination of invention: A method for preparing chlorogenic acid by comprehensive utilization of stevia leaves as a raw material and the prepared chlorogenic acid Effective date of registration: 20220902 Granted publication date: 20220415 Pledgee: Bank of Weifang Zhucheng sub branch Pledgor: ZHUCHENG HAOTIAN PHARM Co.,Ltd. Registration number: Y2022980014355 |
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Date of cancellation: 20231016 Granted publication date: 20220415 Pledgee: Bank of Weifang Zhucheng sub branch Pledgor: ZHUCHENG HAOTIAN PHARM Co.,Ltd. Registration number: Y2022980014355 |
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