JPS6232173B2 - - Google Patents

Info

Publication number: JPS6232173B2
Authority: JP; Japan
Prior art keywords: baicalin; water; purity; methanol; solution
Prior art date: 1984-08-20
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.): Expired

Application number

JP59173538A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6150921A (ja

Inventor

Makoto Tsuboi

Yutaka Ando

Kenji Matsui

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Ichimaru Pharcos Co Ltd

Original Assignee

Ichimaru Pharcos Co Ltd

Priority date (The priority date 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 date listed.)

1984-08-20

Filing date

1984-08-20

Publication date

1987-07-13

1984-08-20 Application filed by Ichimaru Pharcos Co Ltd filed Critical Ichimaru Pharcos Co Ltd

1984-08-20 Priority to JP59173538A priority Critical patent/JPS6150921A/ja

1986-03-13 Publication of JPS6150921A publication Critical patent/JPS6150921A/ja

1987-07-13 Publication of JPS6232173B2 publication Critical patent/JPS6232173B2/ja

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 63
IPQKDIRUZHOIOM-UHFFFAOYSA-N Oroxin A Natural products OC1C(O)C(O)C(CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IPQKDIRUZHOIOM-UHFFFAOYSA-N 0.000 claims description 59
IKIIZLYTISPENI-ZFORQUDYSA-N baicalin Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 IKIIZLYTISPENI-ZFORQUDYSA-N 0.000 claims description 59
229960003321 baicalin Drugs 0.000 claims description 59
AQHDANHUMGXSJZ-UHFFFAOYSA-N baicalin Natural products OC1C(O)C(C(O)CO)OC1OC(C(=C1O)O)=CC2=C1C(=O)C=C(C=1C=CC=CC=1)O2 AQHDANHUMGXSJZ-UHFFFAOYSA-N 0.000 claims description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 43
238000000034 method Methods 0.000 claims description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
239000000706 filtrate Substances 0.000 claims description 11
239000004952 Polyamide Substances 0.000 claims description 10
229920002647 polyamide Polymers 0.000 claims description 10
238000009835 boiling Methods 0.000 claims description 7
239000013078 crystal Substances 0.000 claims description 7
239000001913 cellulose Substances 0.000 claims description 4
229920002678 cellulose Polymers 0.000 claims description 4
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
239000007788 liquid Substances 0.000 description 17
FXNFHKRTJBSTCS-UHFFFAOYSA-N Baicalein Natural products C=1C(=O)C=2C(O)=C(O)C(O)=CC=2OC=1C1=CC=CC=C1 FXNFHKRTJBSTCS-UHFFFAOYSA-N 0.000 description 16
UDFLTIRFTXWNJO-UHFFFAOYSA-N baicalein Chemical compound O1C2=CC(=O)C(O)=C(O)C2=C(O)C=C1C1=CC=CC=C1 UDFLTIRFTXWNJO-UHFFFAOYSA-N 0.000 description 16
229940015301 baicalein Drugs 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
238000005238 degreasing Methods 0.000 description 7
238000001914 filtration Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000007796 conventional method Methods 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
206010020649 Hyperkeratosis Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
-1 Cephadex-LH20 Polymers 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
229920000299 Nylon 12 Polymers 0.000 description 2
229920002302 Nylon 6,6 Polymers 0.000 description 2
208000003251 Pruritus Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
238000012136 culture method Methods 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000002386 leaching Methods 0.000 description 2
239000000843 powder Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 1
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
244000163122 Curcuma domestica Species 0.000 description 1
235000003392 Curcuma domestica Nutrition 0.000 description 1
241001656769 Lilium canadense Species 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
244000088415 Raphanus sativus Species 0.000 description 1
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
244000061458 Solanum melongena Species 0.000 description 1
235000002597 Solanum melongena Nutrition 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
229940107816 ammonium iodide Drugs 0.000 description 1
238000012443 analytical study Methods 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
244000309464 bull Species 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
235000003373 curcuma longa Nutrition 0.000 description 1
230000007423 decrease Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
229930003944 flavone Natural products 0.000 description 1
150000002213 flavones Chemical class 0.000 description 1
235000011949 flavones Nutrition 0.000 description 1
229930003935 flavonoid Natural products 0.000 description 1
150000002215 flavonoids Chemical class 0.000 description 1
235000017173 flavonoids Nutrition 0.000 description 1
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000007803 itching Effects 0.000 description 1
239000002075 main ingredient Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000002791 soaking Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
235000013976 turmeric Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000003809 water extraction Methods 0.000 description 1

Landscapes

Pyrane Compounds (AREA)
Medicines Containing Plant Substances (AREA)

JP59173538A 1984-08-20 1984-08-20 バイカリンの精製化法 Granted JPS6150921A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP59173538A JPS6150921A (ja)	1984-08-20	1984-08-20	バイカリンの精製化法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP59173538A JPS6150921A (ja)	1984-08-20	1984-08-20	バイカリンの精製化法

Publications (2)

Publication Number	Publication Date
JPS6150921A JPS6150921A (ja)	1986-03-13
JPS6232173B2 true JPS6232173B2 (es)	1987-07-13

Family

ID=15962387

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP59173538A Granted JPS6150921A (ja)	1984-08-20	1984-08-20	バイカリンの精製化法

Country Status (1)

Country	Link
JP (1)	JPS6150921A (es)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH04103977U (ja) *	1991-02-18	1992-09-08	株式会社ニフコ	ラツチ装置
JPH09216827A (ja) *	1996-02-09	1997-08-19	Sunstar Inc	毛母細胞賦活剤およびそれを配合してなる養毛剤組成物

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* Cited by examiner, † Cited by third party
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WO1996002528A1 (fr) *	1994-07-14	1996-02-01	Tsumura & Co.	Procede de separation et de recuperation de composes de la flavone a structure glycosidique et composes de la flavone ne presentant pas de structure glycosidique
US7108868B2 (en)	2002-03-22	2006-09-19	Unigen Pharmaceuticals, Inc.	Isolation of a dual cox-2 and 5-lipoxygenase inhibitor from acacia
US7972632B2 (en)	2003-02-28	2011-07-05	Unigen Pharmaceuticals, Inc.	Identification of Free-B-Ring flavonoids as potent COX-2 inhibitors
EP1495764A4 (en) *	2002-04-15	2005-11-16	Tetsuo Santo	TEA DRINK FOR THE TREATMENT OF DERMATITIS
JP4723239B2 (ja)	2002-04-30	2011-07-13	ユニジェン・インコーポレーテッド	治療剤としての遊離−ｂ−環フラボノイド類とフラバン類との混合物の製剤
US8945518B2 (en)	2002-04-30	2015-02-03	Unigen, Inc.	Formulation of dual eicosanoid system and cytokine system inhibitors for use in the prevention and treatment of oral diseases and conditions
AU2004228021B2 (en)	2003-04-04	2010-09-02	Unigen, Inc.	Formulation of dual cycloxygenase (COX) and lipoxygenase (LOX) inhibitors for mammal skin care
WO2005077929A1 (en) *	2004-02-09	2005-08-25	Cargill, Incorporated	Phenolic compound purification
KR100761248B1 (ko)	2006-10-12	2007-10-04	주식회사 유니젠	대나무 및 황금 추출물을 유효성분으로 함유하는 아토피성피부염 치료를 위한 조성물
CN102311469B (zh) *	2011-09-16	2014-06-04	陕西科技大学	一种利用黄芩毛状根生产黄芩苷的方法
CN103694294A (zh) *	2014-01-10	2014-04-02	河南智晶生物科技有限公司	利用闪提技术提取黄芩苷的方法
CN104650165B (zh) *	2015-02-27	2017-10-13	山东省分析测试中心	一种黄芩苷的制备方法
CN105732753B (zh) *	2016-02-01	2018-03-06	承德医学院	一种黄芩苷镁化合物及其制备方法与它的用途
CN109320569A (zh) *	2017-08-01	2019-02-12	湘潭大学	一种从黄芩中提取高***芩苷的方法

1984
- 1984-08-20 JP JP59173538A patent/JPS6150921A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH04103977U (ja) *	1991-02-18	1992-09-08	株式会社ニフコ	ラツチ装置
JPH09216827A (ja) *	1996-02-09	1997-08-19	Sunstar Inc	毛母細胞賦活剤およびそれを配合してなる養毛剤組成物

Also Published As

Publication number	Publication date
JPS6150921A (ja)	1986-03-13

Publication	Publication Date	Title
JPS6232173B2 (es)	1987-07-13
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JPS6365075B2 (es)	1988-12-14
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JPS6232173B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15962387

Family Applications (1)

Country Status (1)

Cited By (2)

Families Citing this family (14)

Cited By (2)

Also Published As

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