CN103819439B - 橙皮苷一锅煮法制备香叶木素 - Google Patents
橙皮苷一锅煮法制备香叶木素 Download PDFInfo
- Publication number
- CN103819439B CN103819439B CN201410042948.3A CN201410042948A CN103819439B CN 103819439 B CN103819439 B CN 103819439B CN 201410042948 A CN201410042948 A CN 201410042948A CN 103819439 B CN103819439 B CN 103819439B
- Authority
- CN
- China
- Prior art keywords
- diosmetin
- hesperidin
- reaction
- fine work
- prepares
- 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.)
- Expired - Fee Related
Links
- QAGGICSUEVNSGH-UHFFFAOYSA-N Diosmetin Natural products C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=CC=C(O)C=C2O1 QAGGICSUEVNSGH-UHFFFAOYSA-N 0.000 title claims abstract description 57
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical compound C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 229960001876 diosmetin Drugs 0.000 title claims abstract description 57
- 235000015428 diosmetin Nutrition 0.000 title claims abstract description 57
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 41
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 41
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 title claims abstract description 41
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 title claims abstract description 41
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 title claims abstract description 41
- 229940025878 hesperidin Drugs 0.000 title claims abstract description 41
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000005580 one pot reaction Methods 0.000 title claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000012043 crude product Substances 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000004806 packaging method and process Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000008213 purified water Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 claims description 6
- -1 methane amide Chemical class 0.000 claims description 6
- 235000011837 pasties Nutrition 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 3
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 claims description 3
- 238000003916 acid precipitation Methods 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- 239000000243 solution Substances 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 230000008030 elimination Effects 0.000 claims 2
- 238000003379 elimination reaction Methods 0.000 claims 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 9
- 238000005516 engineering process Methods 0.000 abstract description 7
- 238000007039 two-step reaction Methods 0.000 abstract description 4
- 239000007791 liquid phase Substances 0.000 abstract description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 230000007423 decrease Effects 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- GZSOSUNBTXMUFQ-NJGQXECBSA-N 5,7,3'-Trihydroxy-4'-methoxyflavone 7-O-rutinoside Natural products O(C[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](Oc2cc(O)c3C(=O)C=C(c4cc(O)c(OC)cc4)Oc3c2)O1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 GZSOSUNBTXMUFQ-NJGQXECBSA-N 0.000 description 11
- GZSOSUNBTXMUFQ-YFAPSIMESA-N diosmin Chemical compound C1=C(O)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(O)C=C2O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)O1 GZSOSUNBTXMUFQ-YFAPSIMESA-N 0.000 description 11
- 229960004352 diosmin Drugs 0.000 description 11
- IGBKNLGEMMEWKD-UHFFFAOYSA-N diosmin Natural products COc1ccc(cc1)C2=C(O)C(=O)c3c(O)cc(OC4OC(COC5OC(C)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 IGBKNLGEMMEWKD-UHFFFAOYSA-N 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- AIONOLUJZLIMTK-AWEZNQCLSA-N hesperetin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O)=CC(O)=C2C(=O)C1 AIONOLUJZLIMTK-AWEZNQCLSA-N 0.000 description 6
- 229960001587 hesperetin Drugs 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000005502 peroxidation Methods 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 125000005425 toluyl group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 238000012946 outsourcing Methods 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 244000248349 Citrus limon Species 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 235000009088 Citrus pyriformis Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000002790 anti-mutagenic effect Effects 0.000 description 1
- 230000000703 anti-shock 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
- 230000036760 body temperature Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 101150055214 cyp1a1 gene Proteins 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- 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
- C07D311/30—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 not hydrogenated in the hetero ring, e.g. flavones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410042948.3A CN103819439B (zh) | 2014-01-21 | 2014-01-21 | 橙皮苷一锅煮法制备香叶木素 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201410042948.3A CN103819439B (zh) | 2014-01-21 | 2014-01-21 | 橙皮苷一锅煮法制备香叶木素 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103819439A CN103819439A (zh) | 2014-05-28 |
CN103819439B true CN103819439B (zh) | 2015-11-25 |
Family
ID=50754771
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201410042948.3A Expired - Fee Related CN103819439B (zh) | 2014-01-21 | 2014-01-21 | 橙皮苷一锅煮法制备香叶木素 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN103819439B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109180627B (zh) * | 2018-09-06 | 2020-11-10 | 陕西嘉禾生物科技股份有限公司 | 一种香叶木素的半合成方法 |
CN109662932A (zh) * | 2019-03-05 | 2019-04-23 | 王忠良 | 一种保湿抗皱化妆品 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1544427A (zh) * | 2003-11-20 | 2004-11-10 | 黑龙江大学 | 木犀草素的半合成方法 |
CN103145668A (zh) * | 2013-01-07 | 2013-06-12 | 李玉山 | 一种橙皮苷制备木犀草素的新技术 |
-
2014
- 2014-01-21 CN CN201410042948.3A patent/CN103819439B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1544427A (zh) * | 2003-11-20 | 2004-11-10 | 黑龙江大学 | 木犀草素的半合成方法 |
CN103145668A (zh) * | 2013-01-07 | 2013-06-12 | 李玉山 | 一种橙皮苷制备木犀草素的新技术 |
Also Published As
Publication number | Publication date |
---|---|
CN103819439A (zh) | 2014-05-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105732744B (zh) | 一种地奥司明的制备方法 | |
CN101168522B (zh) | 一种由万寿菊油树脂制备高纯度叶黄素晶体的方法 | |
CN102558572B (zh) | 离子液体溶剂中木质素乙酰化的制备方法 | |
CN105384788A (zh) | 一种泰地罗新的制备方法 | |
CN103819439B (zh) | 橙皮苷一锅煮法制备香叶木素 | |
CN103450316B (zh) | 一种同时提取茶皂素、茶籽黄酮苷和茶多糖的方法 | |
CN101570543A (zh) | 一种美洛西林钠溶媒结晶制备方法 | |
CN105272838A (zh) | 巨大戟醇提取物的分离纯化方法 | |
CN102351939A (zh) | 一种从女贞中联合制备高纯度熊果酸和齐墩果酸的方法 | |
CN102659902A (zh) | 一种从茶粕中提取高纯茶皂素的工艺 | |
CN100410222C (zh) | 从低含量茄尼醇浸膏中提取高纯茄尼醇的方法 | |
CN102351933A (zh) | 一种制备羟钴胺盐的方法 | |
CN102659572B (zh) | 一种脱氢松香酸的制备方法 | |
CN103819438A (zh) | 柚皮苷一步法制备芹菜素新技术 | |
CN112680496B (zh) | 一种提取薯蓣皂苷元的生产工艺 | |
CN1310873C (zh) | 一种高纯度dl-赖氨酸的生产方法 | |
CN110790811A (zh) | 双相体系氯化铝水解制备薯蓣皂素方法 | |
CN106432386A (zh) | 一种以柚皮苷为原料合成新橙皮苷的方法 | |
CN103012524B (zh) | 一种半合成制备漆叶苷的方法 | |
CN108911999B (zh) | 一种1-氨基蒽醌的合成方法 | |
CN100506763C (zh) | 一种溶析结晶纯化联苯的方法 | |
CN103435666B (zh) | 一种香叶木苷的生产新技术 | |
CN114306363B (zh) | 一种工业化制备柑橘黄酮原料药的方法 | |
CN102675106A (zh) | 一种铝盐沉淀制备高纯度绿原酸的方法 | |
CN102584917A (zh) | 高纯度灯盏花乙素原料药的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180411 Address after: 710075 Shaanxi city of Xi'an province high tech Zone rexin Road No. 25 building room 11604 Patentee after: Shaanxi Huifeng Pharmaceutical Co., Ltd. Address before: 710075 Shaanxi Province, Xi'an City High Road No. 25 building 16D enjoye Patentee before: Li Yushan |
|
TR01 | Transfer of patent right | ||
DD01 | Delivery of document by public notice |
Addressee: Li Yushan Document name: Notification of Passing Examination on Formalities |
|
DD01 | Delivery of document by public notice | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20151125 Termination date: 20190121 |
|
CF01 | Termination of patent right due to non-payment of annual fee |