CN113666977A - Production process for combined separation of multiple active ingredients of liquorice - Google Patents
Production process for combined separation of multiple active ingredients of liquorice Download PDFInfo
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- CN113666977A CN113666977A CN202110943089.5A CN202110943089A CN113666977A CN 113666977 A CN113666977 A CN 113666977A CN 202110943089 A CN202110943089 A CN 202110943089A CN 113666977 A CN113666977 A CN 113666977A
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- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 title claims abstract description 51
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
- 244000303040 Glycyrrhiza glabra Species 0.000 title claims abstract description 16
- 235000011477 liquorice Nutrition 0.000 title claims abstract description 14
- 239000004480 active ingredient Substances 0.000 title claims abstract description 13
- 238000000926 separation method Methods 0.000 title description 10
- 239000000047 product Substances 0.000 claims abstract description 68
- GSZUGBAEBARHAW-UHFFFAOYSA-N sophoraflavone B Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C=2OC3=CC(O)=CC=C3C(=O)C=2)C=C1 GSZUGBAEBARHAW-UHFFFAOYSA-N 0.000 claims abstract description 53
- JBQATDIMBVLPRB-UHFFFAOYSA-N isoliquiritigenin Natural products OC1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 JBQATDIMBVLPRB-UHFFFAOYSA-N 0.000 claims abstract description 38
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims abstract description 36
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229960004949 glycyrrhizic acid Drugs 0.000 claims abstract description 36
- 235000019410 glycyrrhizin Nutrition 0.000 claims abstract description 36
- 238000001035 drying Methods 0.000 claims abstract description 35
- KSDSYIXRWHRPMN-UHFFFAOYSA-N 4'-O-beta-D-Galactopyranoside-6''-p-Coumaroylprunin-4',5,7-Trihydroxyflavanone Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C2OC3=CC(O)=CC(O)=C3C(=O)C2)C=C1 KSDSYIXRWHRPMN-UHFFFAOYSA-N 0.000 claims abstract description 34
- DEMKZLAVQYISIA-ONJCETCRSA-N Liquiritin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)c1ccc([C@@H]2Oc3c(C(=O)C2)ccc(O)c3)cc1 DEMKZLAVQYISIA-ONJCETCRSA-N 0.000 claims abstract description 34
- DEMKZLAVQYISIA-UHFFFAOYSA-N Liquirtin Natural products OC1C(O)C(O)C(CO)OC1OC1=CC=C(C2OC3=CC(O)=CC=C3C(=O)C2)C=C1 DEMKZLAVQYISIA-UHFFFAOYSA-N 0.000 claims abstract description 34
- DEMKZLAVQYISIA-ZRWXNEIDSA-N liquiritin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C([C@H]2OC3=CC(O)=CC=C3C(=O)C2)C=C1 DEMKZLAVQYISIA-ZRWXNEIDSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000010438 heat treatment Methods 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 238000003756 stirring Methods 0.000 claims abstract description 25
- 239000006228 supernatant Substances 0.000 claims abstract description 20
- FURUXTVZLHCCNA-UHFFFAOYSA-N Liquiritigenin Natural products C1=CC(O)=CC=C1C1OC2=CC(O)=CC=C2C(=O)C1 FURUXTVZLHCCNA-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000001914 filtration Methods 0.000 claims abstract description 19
- DXDRHHKMWQZJHT-FPYGCLRLSA-N isoliquiritigenin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)C1=CC=C(O)C=C1O DXDRHHKMWQZJHT-FPYGCLRLSA-N 0.000 claims abstract description 19
- 235000008718 isoliquiritigenin Nutrition 0.000 claims abstract description 19
- FURUXTVZLHCCNA-AWEZNQCLSA-N liquiritigenin Chemical compound C1=CC(O)=CC=C1[C@H]1OC2=CC(O)=CC=C2C(=O)C1 FURUXTVZLHCCNA-AWEZNQCLSA-N 0.000 claims abstract description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000001685 glycyrrhizic acid Substances 0.000 claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000012452 mother liquor Substances 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 11
- 239000012043 crude product Substances 0.000 claims abstract description 10
- ILRKKHJEINIICQ-OOFFSTKBSA-N Monoammonium glycyrrhizinate Chemical compound N.O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@H]1CC[C@]2(C)[C@H]3C(=O)C=C4[C@@H]5C[C@](C)(CC[C@@]5(CC[C@@]4(C)[C@]3(C)CC[C@H]2C1(C)C)C)C(O)=O)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O ILRKKHJEINIICQ-OOFFSTKBSA-N 0.000 claims abstract description 9
- 238000004042 decolorization Methods 0.000 claims abstract description 9
- 239000008213 purified water Substances 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- 239000004378 Glycyrrhizin Substances 0.000 claims description 20
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 13
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 12
- 230000005484 gravity Effects 0.000 claims description 8
- 230000001376 precipitating effect Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 4
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 abstract 1
- 235000013923 monosodium glutamate Nutrition 0.000 abstract 1
- 239000004223 monosodium glutamate Substances 0.000 abstract 1
- 238000001291 vacuum drying Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 17
- 241000202807 Glycyrrhiza Species 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 9
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 9
- 229940010454 licorice Drugs 0.000 description 9
- 238000000605 extraction Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229930003935 flavonoid Natural products 0.000 description 5
- 235000017173 flavonoids Nutrition 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000002215 flavonoids Chemical class 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- LTINPJMVDKPJJI-UHFFFAOYSA-N iodinated glycerol Chemical compound CC(I)C1OCC(CO)O1 LTINPJMVDKPJJI-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 240000008917 Glycyrrhiza uralensis Species 0.000 description 2
- 235000000554 Glycyrrhiza uralensis Nutrition 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 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 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IEDZUWZMVFTGHG-UHFFFAOYSA-N ethyl acetate;ethyl formate Chemical compound CCOC=O.CCOC(C)=O IEDZUWZMVFTGHG-UHFFFAOYSA-N 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241001678559 COVID-19 virus Species 0.000 description 1
- 241000711573 Coronaviridae Species 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241001278898 Glycyrrhiza inflata Species 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229930194248 Licoflavone Natural products 0.000 description 1
- MEHHCBRCXIDGKZ-UHFFFAOYSA-N Licoflavone C Natural products CC(C)=CCC1=C(O)C=C(O)C(C(C=2)=O)=C1OC=2C1=CC=C(O)C=C1 MEHHCBRCXIDGKZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000012356 Product development Methods 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 210000004903 cardiac system Anatomy 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002207 flavanone derivatives Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- -1 flavonoid compounds Chemical class 0.000 description 1
- LBQIJVLKGVZRIW-ZDUSSCGKSA-N glabridin Chemical compound C1([C@H]2CC3=CC=C4OC(C=CC4=C3OC2)(C)C)=CC=C(O)C=C1O LBQIJVLKGVZRIW-ZDUSSCGKSA-N 0.000 description 1
- PMPYOYXFIHXBJI-ZDUSSCGKSA-N glabridin Natural products C1([C@H]2CC=3C=CC4=C(C=3OC2)CCC(O4)(C)C)=CC=C(O)C=C1O PMPYOYXFIHXBJI-ZDUSSCGKSA-N 0.000 description 1
- 229940093767 glabridin Drugs 0.000 description 1
- LBQIJVLKGVZRIW-UHFFFAOYSA-N glabridine Natural products C1OC2=C3C=CC(C)(C)OC3=CC=C2CC1C1=CC=C(O)C=C1O LBQIJVLKGVZRIW-UHFFFAOYSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention relates to a production process for jointly separating multiple active ingredients of liquorice, which comprises the following steps: the method comprises the steps of stirring and extracting mother liquor powder and a solvent after production of mono-ammonium glycyrrhizinate at room temperature to obtain an extracting solution and a solvent insoluble part; filtering, recovering, dissolving, drying and crushing the extracting solution to obtain a product A; adding purified water into the product A, and heating, stirring and extracting to obtain a supernatant and a product B; concentrating the supernatant under reduced pressure, adding 95% ethanol, and heating to dissolve; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain liquiritin with the content of more than 90%; carrying out vacuum drying and normal-pressure heating on the solvent-insoluble part to obtain a product C, and drying and crushing the product C to obtain the debitterized liquorice monosodium glutamate with the glycyrrhizic acid content of more than 10%; and fourthly, drying and crushing the product B in vacuum to obtain crude products of liquiritigenin and isoliquiritigenin with the content of 8-15%. The method has the advantages of simple process, low cost and high safety, and is suitable for industrial mass production.
Description
Technical Field
The invention relates to the field of food and medicine, in particular to a production process for jointly separating multiple active ingredients of liquorice.
Background
Licorice (Glycyrrhiza uralensis Fisch) is a plant belonging to genus Glycyrrhiza of family Leguminosae, and has 29 varieties of 6 varieties in the whole world, wherein 18 varieties of 3 varieties exist in China and are widely distributed in northwest, north China, northeast China and other areas, and meanwhile, Glycyrrhiza uralensis, Glycyrrhiza inflata and Glycyrrhiza glabra are one of the basic plants of medicinal material licorice, and are widely applied to industries such as medicine, food, cosmetics and the like.
The main active components of Glycyrrhrizae radix extract include glycyrrhizic acid and its multiple analogues of glycyrrhizin, Glycyrrhrizae radix total flavonoids such as liquiritin, liquiritigenin, isoliquiritigenin, glabridin, etc., and Glycyrrhrizae radix polysaccharide.
The Liquiritin (Liquiritin) is an important monomer active component in flavonoid compounds and has strong pharmacological activity, researches show that the Liquiritin has obvious antidepressant effect, neuroprotective effect on nerve cell injury and protective effect on cardiac system and liver toxicity, in addition, the Liquiritin has various activities of antivirus and anti-inflammation, recent research results of big research teams show that the Liquiritin can inhibit the replication of novel coronavirus, and the Liquiritin is expected to be developed into a new medicine for resisting SARS-CoV-2. Liquiritigenin (liquiritigenin) is a flavanone monomer compound existing in Glycyrrhrizae radix, and has physiological effects of resisting cancer, ulcer, inflammation and protecting liver. Isoglycyrrhiza is a "strong analog" of the organ transplant rejection drug "rapamycin" in its natural products. Glycyrrhizic acid has antiinflammatory and antiviral effects, and also has pharmacological effects of resisting bacteria, resisting cancer, resisting allergy, resisting blood coagulation activity, and removing local excessive fat. Glycyrrhizic acid can also be used as raw material to prepare glycyrrhizin, which is widely used in food field.
Qinghai lake pharmaceutical industry Co., Ltd applies for a patent (application number: 201610229840.4) named as "a method for separating and purifying liquiritin", which adopts 2 times of extraction and enrichment of extract, silica gel column chromatography separation and crystallization to obtain high-purity liquiritin. However, the extracting solution used in the process is methanol, chloroform, dichloromethane and the like, and the organic solvents such as benzene, toluene and the like used in the purification of a chromatographic column have strong toxicity, and the use of the organic solvents can cause solvent residue to influence the quality of liquiritin; the process uses silica gel column for separation and purification, and the silica gel is not easy to regenerate, so that the use times of the silica gel are limited, and the silica gel cannot be repeatedly used, so that the production cost is high; the flash point of the ethyl acetate used for chromatographic separation is low, and potential safety hazards exist; only one product of liquiritin is used, the glycyrrhizin and the total flavone in the ammoniation mother liquor cream are not comprehensively utilized, the production cost is high, the waste is caused, and the environment is polluted.
A patent (application number: 201110287907.7) named as a method for extracting liquiritin from liquorice is applied by Tianjin peak natural product development limited company, and the patent process comprises the steps of crushing liquorice, extracting with deionized water, filtering to obtain liquiritin crude extract, and then separating, purifying and recrystallizing the crude extract on a mixed resin column to obtain the liquiritin. However, the process only extracts and separates the liquiritin from the liquorice, discards other important functional components in the liquorice, such as glycyrrhizic acid and general flavone, and has no comprehensive utilization, only theoretical significance and no market prospect.
A patent named 'liquiritin and a preparation method thereof' is applied by Jiangsu Tiancheng pharmaceutical industry Co., Ltd (application number: 201010579521.9). the patent process comprises the steps of firstly ammoniating glycyrrhizic acid powder, extracting to obtain liquiritin, then separating, purifying and crystallizing by using a polyamide column to obtain the liquiritin. The process only extracts and separates liquiritin from liquorice, and discards other important functional components in the liquorice, such as glycyrrhizic acid and total flavonoids, which are not comprehensively utilized. Also has high production cost and no market competitiveness.
The university of Chinese academy of sciences applies for a patent (application number: 200710011041.0) named as a preparation method of liquiritin, the technology of the patent extracts and deposits liquiritin by alcohol, separates the liquiritin by a molecular membrane separator, macroporous resin and a high-efficiency industrial chromatographic column in sequence, and freezes and dries to obtain the liquiritin, and the technology is complex, has high requirements on equipment, large operation difficulty and long time consumption, and is not suitable for industrial mass production.
Gansu pan-plant medicine industry Co., Ltd applies for a process for the combined separation of high purity glycyrrhizin, bitter-removed glycyrrhizin and licorice total flavonoids from a glycyrrhiza monoammonium salt mother liquor paste (application No. 202011128456.8), the process comprises eluting the glycyrrhiza monoammonium salt mother liquor paste with different types of resins to obtain the glycyrrhizin and co-produce glycyrrhizin and licoflavone, although the raw materials can be fully and effectively utilized, the flavonoid components such as glycyrrhizin and isoliquiritigenin which coexist with the glycyrrhizin are not classified and collected, the macroporous resin elution solvent consumption is large, and the operation is complicated and is not convenient for large-scale production.
In conclusion, the prior art has the defects of complex process, high requirement on equipment, high operation difficulty, use of various organic solvents which easily cause potential safety hazards, incomplete and effective utilization of raw materials, low additional value, high production cost and the like.
Disclosure of Invention
The invention aims to solve the technical problem of providing a production process for jointly separating multiple licorice active ingredients with low cost and high safety.
In order to solve the problems, the production process for jointly separating multiple active ingredients of liquorice comprises the following steps:
the method comprises the steps of respectively adding mother liquor powder and a solvent after production of mono-ammonium glycyrrhizinate into a reaction vessel, stirring and extracting for 2-3 times at room temperature to respectively obtain an extracting solution and a solvent insoluble part;
filtering, recovering, dissolving, drying and crushing the extracting solution to obtain a product A; adding purified water with the mass being 4-15 times that of the product A into the product A, heating, stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B; concentrating the supernatant under reduced pressure until the specific gravity is 1.15-1.20 at 60 ℃, adding ethanol with the volume concentration of 95%, and heating to dissolve the ethanol; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain liquiritin with the content of more than 90%;
thirdly, drying the solvent-insoluble part in vacuum and heating at normal pressure until the solvent is completely volatilized to obtain a product C, and drying and crushing the product C to obtain the debitterized glycyrrhizin with the glycyrrhizic acid content of more than 10%;
and fourthly, drying and crushing the product B in vacuum to obtain crude products of liquiritigenin and isoliquiritigenin with the content of 8-15%.
The solvent in the step is one of ethyl acetate, ethyl formate or a mixed liquid of ethyl acetate and ethyl formate.
The volume of the solvent in the step is 3-5 BV of the mother liquid powder.
The heating, stirring and extracting conditions in the step II are that the temperature is 40-100 ℃, the extracting times are 2-3 times, and the extracting time is 1-2 hours each time.
In the step II, the addition amount of the ethanol is 0.2-6 BV of the supernatant.
Compared with the prior art, the invention has the following advantages:
1. the resource utilization rate is high, and the added value of the product is high:
the invention adopts a scientific and feasible method to separate and prepare high-purity liquiritin (content 90%), flavonoid-removed glycyrrhizin (glycyrrhizic acid content is more than 10%) and crude liquiritigenin and isoliquiritigenin (content is 8-15%) from ammonium glycyrrhetate mother liquor powder through the steps of dissolution and combined separation of different solvents, crystallization, recrystallization and the like. Compared with the prior art, the obtained liquiritin has high purity, and simultaneously, three products of flavonoid-removed glycyrrhizin, crude liquiritigenin and isoliquiritigenin are co-produced, so that the raw materials can be fully and effectively utilized.
2. The production safety is high:
in the invention, only two organic solvents of edible solvents of ethyl acetate, methyl acetate and ethanol are used, other organic solvents with low flammable and explosive flash points are not used, other organic solvent residues are avoided, and the potential safety hazard in the production process can be reduced.
3. The production cost is low:
the solvents used in the invention can be recycled, thereby reducing the emission and the production cost.
4. Is suitable for large-scale industrial production:
the method has the advantages of simple process, simple and convenient operation, easy realization of standardization and automation, and is suitable for industrial large-scale production.
Detailed Description
A production process for jointly separating multiple active ingredients of liquorice comprises the following steps:
the method comprises the steps of adding mother liquor powder and a solvent after production of mono-ammonium glycyrrhizinate into a reaction vessel, stirring and extracting for 2-3 times at room temperature, and obtaining an extracting solution and a solvent insoluble part respectively.
Wherein: the solvent is one of ethyl acetate, ethyl formate or a mixture of the ethyl acetate and the ethyl formate. The volume of the solvent is 3-5 BV of the mother liquor powder.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain a product A; and adding purified water with the mass being 4-15 times of that of the product A into the product A, heating and stirring the product A at the temperature of 40-100 ℃, and extracting the product A for 2-3 times, wherein each time of extraction lasts for 1-2 hours. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure until the specific gravity is 1.15-1.20 (60 ℃), adding 0.2-6 BV of ethanol with the volume concentration of 95%, and heating to dissolve the ethanol; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain the liquiritin with the content of more than 90%.
And thirdly, drying the solvent-insoluble part in vacuum, heating under normal pressure until the solvent is volatilized completely to obtain a product C, and drying and crushing the product C to obtain the debitterized glycyrrhizin (namely the flavonoid-removed glycyrrhizin) with the glycyrrhizic acid content of more than 10%.
And fourthly, drying and crushing the product B in vacuum to obtain crude products of liquiritigenin and isoliquiritigenin with the content of 8-15%. The crude product can be used as raw material for preparing high-content glycyrrhizin and isoliquiritigenin.
Example 1 a process for the combined separation of multiple active ingredients of licorice, comprising the steps of:
firstly, adding 10kg of mother liquor powder after producing mono-ammonium glycyrrhizinate into a jacketed kettle, adding 50L of ethyl acetate each time, stirring and extracting for 3 times at room temperature to respectively obtain an extracting solution and an ethyl acetate insoluble substance.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain 3.5kg of a product A; and adding the product A into a jacketed kettle, adding 12L of purified water each time, heating and stirring at 100 ℃, and extracting for 3 times, wherein the extraction time is 1-2 hours each time. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure to obtain fluid extract with a specific gravity of 1.15 (60 deg.C) 2.5kg, adding 5BV ethanol with a volume concentration of 95%, and heating to dissolve; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain 306g of white solid liquiritin with the content of 92.7 percent and the weight yield of 3.06 percent.
And thirdly, drying the ethyl acetate insoluble substance in vacuum, heating the ethyl acetate insoluble substance at normal pressure until the solvent in the ethyl acetate insoluble substance is volatilized completely to obtain a product C, and drying and crushing the product C to obtain 6.5kg of the debitterized glycyrrhizin, wherein the glycyrrhizic acid content is 12.42 percent, and the weight yield is 65.0 percent.
And fourthly, drying and crushing the product B in vacuum to obtain 2.8kg of crude product containing the liquiritigenin and the isoliquiritigenin. Wherein: the content of liquiritigenin is 11.20%, the content of isoliquiritigenin is 11.6%, and the weight yield is 28.0%.
Embodiment 2 a process for the combined separation of multiple active ingredients of licorice, comprising the steps of:
firstly, adding 10kg of mother liquor powder after producing mono-ammonium glycyrrhizinate into a jacketed kettle, adding 30L of ethyl acetate each time, stirring and extracting for 3 times at room temperature to respectively obtain an extracting solution and an ethyl acetate insoluble substance.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain 2.8kg of a product A; and adding the product A into a jacketed kettle, adding 0.4L of purified water each time, heating and stirring at 60 ℃, and extracting for 3 times, wherein the extraction time is 1-2 hours each time. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure to obtain fluid extract with a specific gravity of 1.20 (60 deg.C) 2kg, adding 3BV ethanol with a volume concentration of 95%, and heating to dissolve; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain 280g of white solid liquiritin, wherein the content is 96.5 percent, and the weight yield is 2.80 percent.
And thirdly, drying the ethyl acetate insoluble substance in vacuum, heating the ethyl acetate insoluble substance at normal pressure until the solvent in the ethyl acetate insoluble substance is volatilized completely to obtain a product C, and drying and crushing the product C to obtain 7.5kg of the debitterized glycyrrhizin, wherein the glycyrrhizic acid content is 11.38%, and the weight yield is 75.0%.
And fourthly, drying and crushing the product B in vacuum to obtain 2.24kg of crude product containing the liquiritigenin and the isoliquiritigenin. Wherein: the content of liquiritigenin is 12.60%, the content of isoliquiritigenin is 10.8%, and the weight yield is 22.4%.
Example 3 a process for the combined separation of multiple active ingredients of licorice, comprising the steps of:
firstly, adding 10kg of mother liquor powder after producing mono-ammonium glycyrrhizinate into a jacketed kettle, adding 40L of ethyl acetate each time, stirring and extracting for 2 times at room temperature to respectively obtain an extracting solution and an ethyl acetate insoluble substance.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain 2.2kg of a product A; adding the product A into a jacketed kettle, adding 8.8L of purified water each time, heating and stirring at 40 ℃, and extracting for 1 time, wherein the extraction time is 1-2 hours each time. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure to obtain fluid extract 1.5kg with specific gravity of 1.18 (60 deg.C), adding 1L ethanol with volume concentration of 95%, and heating to dissolve; then adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing in sequence to obtain 180g of white solid liquiritin, wherein the content is 91.56%, and the weight yield is 1.80%.
And thirdly, drying the ethyl acetate insoluble substance in vacuum, heating the ethyl acetate insoluble substance at normal pressure until the solvent in the ethyl acetate insoluble substance is volatilized completely to obtain a product C, and drying and crushing the product C to obtain 8.2kg of the debitterized glycyrrhizin, wherein the glycyrrhizic acid content is 10.38 percent, and the weight yield is 82.0 percent.
And fourthly, drying and crushing the product B in vacuum to obtain 1.85kg of crude product containing the liquiritigenin and the isoliquiritigenin. Wherein: the content of liquiritigenin is 10.60%, the content of isoliquiritigenin is 11.23%, and the weight yield is 18.5%.
Example 4 a process for the combined separation of multiple active ingredients of licorice, comprising the steps of:
adding 10kg of mother liquor powder after producing mono-ammonium glycyrrhizinate into a jacketed kettle, adding 60L of ethyl formate each time, stirring and extracting for 2 times at room temperature to obtain an extracting solution and an ethyl formate insoluble substance respectively.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain 2.6kg of a product A; and adding the product A into a jacketed kettle, adding 10.4L of purified water each time, heating and stirring at 80 ℃, and extracting for 2 times, wherein the extraction time is 1-2 hours each time. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure to obtain fluid extract 1.8kg with specific gravity of 1.18 (60 deg.C), adding 0.36L ethanol with volume concentration of 95%, and heating to dissolve; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain 160g of white solid liquiritin with the content of 92.22% and the weight yield of 1.60%.
And thirdly, drying the ethyl formate insoluble substance in vacuum, heating the ethyl formate insoluble substance at normal pressure until the solvent in the ethyl formate insoluble substance is volatilized completely to obtain a product C, and drying and crushing the product C to obtain 7.2kg of the debitterized glycyrrhizin, wherein the glycyrrhizic acid content is 10.68 percent, and the weight yield is 72.0 percent.
And fourthly, drying and crushing the product B in vacuum to obtain 1.95kg of crude product containing the liquiritigenin and the isoliquiritigenin. Wherein: the content of liquiritigenin is 12.60%, the content of isoliquiritigenin is 11.58%, and the weight yield is 19.5%.
Example 5 a process for the combined isolation of multiple active ingredients from licorice, comprising the steps of:
adding 10kg of mother liquor powder after producing mono-ammonium glycyrrhizinate into an interlayer pot, wherein ethyl formate is added each time: ethyl acetate =1:1, and the mixture was stirred and extracted at room temperature for 3 times to obtain an extract and an insoluble ethyl formate-ethyl acetate mixture, respectively.
Filtering, recovering, dissolving, drying and crushing the extracting solution to obtain 3.2kg of a product A; and adding the product A into a jacketed kettle, adding 10.4L of purified water each time, heating and stirring at 80 ℃, and extracting for 2 times, wherein the extraction time is 1-2 hours each time. Stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B. Product B is the water insoluble fraction.
Concentrating the supernatant under reduced pressure to obtain fluid extract with a specific gravity of 1.17 (60 deg.C) 2.1kg, adding 0.36L ethanol with volume concentration of 95%, and heating to dissolve; then adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing in sequence to obtain 188g of white solid liquiritin with the content of 93.50 percent and the weight yield of 1.88 percent.
And thirdly, drying the ethyl formate-ethyl acetate mixed solvent insoluble substance in vacuum, heating the mixture at normal pressure until the solvent in the mixture is volatilized completely to obtain a product C, and drying and crushing the product C to obtain 7.7kg of the debitterized glycyrrhizin, wherein the glycyrrhizic acid content is 13.68 percent, and the weight yield is 77.0 percent.
And fourthly, drying and crushing the product B in vacuum to obtain 1.65kg of crude product containing the liquiritigenin and the isoliquiritigenin. Wherein: the content of the liquiritigenin is 10.60 percent, the content of the isoliquiritigenin is 12.58 percent, and the weight yield is 16.5 percent.
Claims (5)
1. A production process for jointly separating multiple active ingredients of liquorice comprises the following steps:
the method comprises the steps of respectively adding mother liquor powder and a solvent after production of mono-ammonium glycyrrhizinate into a reaction vessel, stirring and extracting for 2-3 times at room temperature to respectively obtain an extracting solution and a solvent insoluble part;
filtering, recovering, dissolving, drying and crushing the extracting solution to obtain a product A; adding purified water with the mass being 4-15 times that of the product A into the product A, heating, stirring, extracting, standing and precipitating to respectively obtain a supernatant and a product B; concentrating the supernatant under reduced pressure until the specific gravity is 1.15-1.20 at 60 ℃, adding ethanol with the volume concentration of 95%, and heating to dissolve the ethanol; then sequentially adding activated carbon for decolorization, filtering, standing for crystallization, separating and recrystallizing to obtain liquiritin with the content of more than 90%;
thirdly, drying the solvent-insoluble part in vacuum and heating at normal pressure until the solvent is completely volatilized to obtain a product C, and drying and crushing the product C to obtain the debitterized glycyrrhizin with the glycyrrhizic acid content of more than 10%;
and fourthly, drying and crushing the product B in vacuum to obtain crude products of liquiritigenin and isoliquiritigenin with the content of 8-15%.
2. The process of claim 1, wherein the process comprises the steps of: the solvent in the step is one of ethyl acetate, ethyl formate or a mixed liquid of ethyl acetate and ethyl formate.
3. The process of claim 1, wherein the process comprises the steps of: the volume of the solvent in the step is 3-5 BV of the mother liquid powder.
4. The process of claim 1, wherein the process comprises the steps of: the heating, stirring and extracting conditions in the step II are that the temperature is 40-100 ℃, the extracting times are 2-3 times, and the extracting time is 1-2 hours each time.
5. The process of claim 1, wherein the process comprises the steps of: in the step II, the addition amount of the ethanol is 0.2-6 BV of the supernatant.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114634534A (en) * | 2022-04-07 | 2022-06-17 | 陕西富捷药业有限公司 | Method for separating monoammonium glycyrrhizinate and liquiritin from monoammonium glycyrrhizinate mother liquor |
| CN115721671A (en) * | 2022-08-12 | 2023-03-03 | 李玉山 | Method for extracting and separating effective components of liquorice root in full-industrial-chain cooperation manner |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803789A (en) * | 2006-01-20 | 2006-07-19 | 华中科技大学 | Method for extracting glycyrrhizicacid, licorice flavone and licorice polysaccharide |
| CN101830962A (en) * | 2010-05-20 | 2010-09-15 | 高颖 | Method for producing glycyrrhizin sodium aliphatate or glycyrrhizin potassium aliphatate |
| CN102633895A (en) * | 2012-04-19 | 2012-08-15 | 南京中医药大学 | Extraction and preparation method by comprehensively utilizing liquorice |
| CN103285074A (en) * | 2013-06-06 | 2013-09-11 | 北京理工大学 | Method for separating glycyrrhiza triterpenes, glycyrrhiza flavonoids and glycyrrhiza polysaccharides |
| CN103833806A (en) * | 2012-11-22 | 2014-06-04 | 天津药物研究院 | Preparation method of traditional Chinese medicine chemical component |
| CN104861015A (en) * | 2015-01-16 | 2015-08-26 | 李玉山 | Synergistic clean extraction method of effective components in licorice root |
| CN110801467A (en) * | 2019-11-13 | 2020-02-18 | 甘肃菁茂生态农业科技股份有限公司 | A method for processing Glycyrrhrizae radix decoction pieces with increased content of liquiritin and glycyrrhizic acid |
| CN112209979A (en) * | 2020-10-20 | 2021-01-12 | 高颖 | Production process for combined separation of high-purity liquiritin, debitterized glycyrrhizin and licorice total flavone from glycyrrhizic acid monoammonium salt mother liquor paste |
-
2021
- 2021-08-17 CN CN202110943089.5A patent/CN113666977A/en active Pending
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1803789A (en) * | 2006-01-20 | 2006-07-19 | 华中科技大学 | Method for extracting glycyrrhizicacid, licorice flavone and licorice polysaccharide |
| CN101830962A (en) * | 2010-05-20 | 2010-09-15 | 高颖 | Method for producing glycyrrhizin sodium aliphatate or glycyrrhizin potassium aliphatate |
| CN102633895A (en) * | 2012-04-19 | 2012-08-15 | 南京中医药大学 | Extraction and preparation method by comprehensively utilizing liquorice |
| CN103833806A (en) * | 2012-11-22 | 2014-06-04 | 天津药物研究院 | Preparation method of traditional Chinese medicine chemical component |
| CN103285074A (en) * | 2013-06-06 | 2013-09-11 | 北京理工大学 | Method for separating glycyrrhiza triterpenes, glycyrrhiza flavonoids and glycyrrhiza polysaccharides |
| CN104861015A (en) * | 2015-01-16 | 2015-08-26 | 李玉山 | Synergistic clean extraction method of effective components in licorice root |
| CN110801467A (en) * | 2019-11-13 | 2020-02-18 | 甘肃菁茂生态农业科技股份有限公司 | A method for processing Glycyrrhrizae radix decoction pieces with increased content of liquiritin and glycyrrhizic acid |
| CN112209979A (en) * | 2020-10-20 | 2021-01-12 | 高颖 | Production process for combined separation of high-purity liquiritin, debitterized glycyrrhizin and licorice total flavone from glycyrrhizic acid monoammonium salt mother liquor paste |
Non-Patent Citations (4)
| Title |
|---|
| 李爱勤: "超声提取联合膜分离技术纯化甘草酸的工艺", 化工设计通讯, vol. 2015, no. 7, pages 350 * |
| 王建国，等: "甘草的活性成分及其在化妆品中的应用", 日用化学工业, vol. 34, no. 4, pages 5 - 7 * |
| 苏本正，等: "甘草饮片乙酸乙酯提取部位HPLC指纹图谱研究", 中成药, vol. 33, no. 2, pages 205 * |
| 赵镭;师清芝;唐星;: "甘草中甘草酸和甘草苷的提取纯化工艺研究", 中国药房, no. 06, pages 426 - 429 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114634534A (en) * | 2022-04-07 | 2022-06-17 | 陕西富捷药业有限公司 | Method for separating monoammonium glycyrrhizinate and liquiritin from monoammonium glycyrrhizinate mother liquor |
| CN114634534B (en) * | 2022-04-07 | 2024-03-19 | 陕西富捷药业有限公司 | Method for separating monoammonium glycyrrhizinate and glycyrrhizin from monoammonium glycyrrhizinate mother liquor |
| CN115721671A (en) * | 2022-08-12 | 2023-03-03 | 李玉山 | Method for extracting and separating effective components of liquorice root in full-industrial-chain cooperation manner |
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