JPS59175449A - シコニンの製造法 - Google Patents
シコニンの製造法Info
- Publication number
- JPS59175449A JPS59175449A JP58050801A JP5080183A JPS59175449A JP S59175449 A JPS59175449 A JP S59175449A JP 58050801 A JP58050801 A JP 58050801A JP 5080183 A JP5080183 A JP 5080183A JP S59175449 A JPS59175449 A JP S59175449A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- shikonin
- naphthoquinone
- line
- compound
- 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
- NEZONWMXZKDMKF-JTQLQIEISA-N Alkannin Chemical compound C1=CC(O)=C2C(=O)C([C@@H](O)CC=C(C)C)=CC(=O)C2=C1O NEZONWMXZKDMKF-JTQLQIEISA-N 0.000 title claims description 37
- UNNKKUDWEASWDN-UHFFFAOYSA-N alkannin Natural products CC(=CCC(O)c1cc(O)c2C(=O)C=CC(=O)c2c1O)C UNNKKUDWEASWDN-UHFFFAOYSA-N 0.000 title claims description 37
- 241001071917 Lithospermum Species 0.000 title claims description 34
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 239000000126 substance Substances 0.000 abstract description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 10
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 abstract description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 2
- FBYIJIHPWCXRHH-UHFFFAOYSA-N 1,4,5,8-tetramethoxynaphthalene-2-carbaldehyde Chemical compound O=CC1=CC(OC)=C2C(OC)=CC=C(OC)C2=C1OC FBYIJIHPWCXRHH-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229930192627 Naphthoquinone Natural products 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 150000002791 naphthoquinones Chemical class 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- NEZONWMXZKDMKF-SNVBAGLBSA-N Shikonin Chemical class C1=CC(O)=C2C(=O)C([C@H](O)CC=C(C)C)=CC(=O)C2=C1O NEZONWMXZKDMKF-SNVBAGLBSA-N 0.000 description 3
- PHTGVPBJVHRZJY-UHFFFAOYSA-N Shikonine Natural products CC(CC=C(C)C)C1=C(O)C(=O)c2c(O)ccc(O)c2C1=O PHTGVPBJVHRZJY-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 241000411851 herbal medicine Species 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 241000118825 Alkanna tinctoria Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000008676 import Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 239000001047 purple dye Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- PPHJIVAGMFRGQJ-UHFFFAOYSA-N (3-acetyloxy-1,4-dioxonaphthalen-2-yl) acetate Chemical compound C1=CC=C2C(=O)C(OC(=O)C)=C(OC(C)=O)C(=O)C2=C1 PPHJIVAGMFRGQJ-UHFFFAOYSA-N 0.000 description 1
- -1 2-(1-acetoxy-4-methyl-3-pentenyl) -5,8-diacetoxy-1,4-naphthoquinone Chemical compound 0.000 description 1
- CZCUIGLMMGPMLC-UHFFFAOYSA-N 5,8-dihydroxy-2-(4-methylpentyl)naphthalene-1,4-dione Chemical compound C1=CC(O)=C2C(=O)C(CCCC(C)C)=CC(=O)C2=C1O CZCUIGLMMGPMLC-UHFFFAOYSA-N 0.000 description 1
- 241000556720 Manga Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241001115903 Raphus cucullatus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000746998 Tragus Species 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 229940091170 naphthoquine Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- ZANGSJPMZXBAEZ-UHFFFAOYSA-M sodium carbonic acid fluoride Chemical compound C(O)(O)=O.[Na+].[F-] ZANGSJPMZXBAEZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58050801A JPS59175449A (ja) | 1983-03-26 | 1983-03-26 | シコニンの製造法 |
| US06/593,135 US4560511A (en) | 1983-03-26 | 1984-03-26 | Method of producing shikonin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58050801A JPS59175449A (ja) | 1983-03-26 | 1983-03-26 | シコニンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59175449A true JPS59175449A (ja) | 1984-10-04 |
| JPS6236021B2 JPS6236021B2 (enExample) | 1987-08-05 |
Family
ID=12868876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58050801A Granted JPS59175449A (ja) | 1983-03-26 | 1983-03-26 | シコニンの製造法 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4560511A (enExample) |
| JP (1) | JPS59175449A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63156741A (ja) * | 1986-12-19 | 1988-06-29 | Piasuaraizu Kk | シコニンの製造方法 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0180791B1 (ko) * | 1995-07-24 | 1999-05-15 | 김용옥 | 6-치환-5,8-디옥시-1,4-나프토퀴논 유도체, 그의 제조방법 및 그의 항암제로서의 용도 |
| GB0117326D0 (en) * | 2001-07-16 | 2001-09-05 | Univ Aberdeen | Napthoquinone-type inhibitors of protein aggregation |
| ES2540248T3 (es) | 2010-10-26 | 2015-07-09 | Omya Development Ag | Producción de carbonato de calcio precipitado de alta pureza |
| CN102211997A (zh) * | 2011-03-28 | 2011-10-12 | 上海交通大学 | 紫草素萘茜母核氧乙酰化衍生物及其制备方法、用途 |
| RU2657548C1 (ru) * | 2017-07-06 | 2018-06-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Дальневосточный государственный медицинский университет" Министерства здравоохранения Российской Федерации (ФГБОУ ВО ДВГМУ Минздрава России) | Гель с нафтохиноновым комплексом биологически активных веществ воробейника краснокорневого |
| CN111808460B (zh) * | 2020-06-12 | 2021-10-01 | 厦门大学 | 紫草素或其衍生物作为防止大型污损生物附着的防污剂的用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3646222A (en) * | 1968-05-20 | 1972-02-29 | Takeda Chemical Industries Ltd | Method for production of substituted hydroquinones |
| DE2700448C2 (de) * | 1977-01-07 | 1982-11-11 | Vassilios P. Priv.-Doz. Dr. Thessaloniki Papageorgiou | Salbe zur Behandlung von Ulcus Cruris |
-
1983
- 1983-03-26 JP JP58050801A patent/JPS59175449A/ja active Granted
-
1984
- 1984-03-26 US US06/593,135 patent/US4560511A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63156741A (ja) * | 1986-12-19 | 1988-06-29 | Piasuaraizu Kk | シコニンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US4560511A (en) | 1985-12-24 |
| JPS6236021B2 (enExample) | 1987-08-05 |
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