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Grundinformationen
- Standard-SMILES
COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2- InChIKey
YBHILYKTIRIUTE-UHFFFAOYSA-N- Summenformel
- C20H18NO4+
- Durchschnittliche Molmasse
- 336,367 g/mol
- Monoisotopische Masse
- 336,12303448
Namen und Bezeichner
- Bevorzugter Name
- Berberine
- IUPAC
- 9,10-Dimethoxy-5,6-dihydro-2H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
- Lokaler Name
- Berberin
- Englischer Name
- Berberine
- Summenformel
- C20H18NO4
- Molmasse
- 336.36
Namen und Synonyme
Datenbank-Bezeichner
- CAS
2086-83-1- PubChem CID
- 2353
- DTXSID
DTXSID9043857- ChEMBL
CHEMBL295124- ChEBI
CHEBI:16118- UNII
- 0I8Y3P32UF
- EC Number
- 218-229-1
- Nikkaji
- J7.320B
Eigenschaften
Physikochemische Eigenschaften
- Schmelzpunkt
- 204 · 204-206 °C (dec.)
- Siedepunkt
- 486.8 °C · 486.8°C (rough estimate)
- Dichte
- 1.2976 · 1.2976 (rough estimate)
- Brechungsindex
- 1.58 · 1.5800 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- Löslichkeit
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- Aggregatzustand
- powder
- pka
- 2.47 · 2.47(at 25℃)
- Farbe
- White to yellow crystals
- Wasserlöslichkeit
- 43.48 g/L · 43.48g/L(25 ºC)
- InChI
- InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
- InChIKey
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- SMILES
- O(C1C(=CC=C2C=1C=[N+]1CCC3=CC4OCOC=4C=C3C1=C2)OC)C
- LogP
- -0.99 · -0.990 (est)
- CAS Datenbank
- 2086 · 2086-83-1(CAS DataBase Reference)
Sicherheit und Regulatorisches
Sicherheitsdaten
- F
- 3-10
- wgk
- 2
- ridadr
- 1544
- RTECS-Nr.
- DR9866400
- Toxizität
- LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62
- hazard_class
- 6.1(b)
- packing_group
- III
Chemie und Industrie
Anwendungen
BeschreibungCoptis chinensis was widely used in China as a folk medicine by Shennong around 3000 BC. Coptis chinensis was first described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic. Coptis chinensis was used to treat intestinal bacterial infections and antipyretic analgesic for thousands of years agoCoptis chinensis also called zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian in Chinese history. Coptis chinensis was accepted by most physicians, and the Chinese pharmacopoeia also uses Coptis chinensis as its official name. Coptis chinensis mainly grows in Anhui, Hunan, Sichuan, and Yunnan and has been cultivated in Sichuan since the Ming dynasty, which has a long history of cultivation. Other species of Coptis chinensis from different places were used as medicine. However, commodity circulation of wild Rhizoma coptidis has not been formed . Coptis chinensis is national three level protection plants at present and majorly produced in Shizhu of Chongqing, West Hubei, Shanxi, and Gansu.Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in some plants such as huanglian (Rhizoma coptidis), huangbo (Phellodendri Chinensis) Cortex), sankezhenthree needles (Berberidis Radix), and so on.The components of Coptis chinensis which have antibacterial and antiinflammatory effects are original alkaloid berberine class, including berberine, coptisine, palmatine, epiberberine, columbamine, jatrorrhizine, worenine, and magnoflorine, with berberine having the highest content (5–8%).
HistoryBerberine is often used in the form of quaternary ammonium alkali. The solubility of berberine in water is lower, for example, berberine hydrochloride is 1:500, and berberine sulfate is 1:30. In 1926, berberine was first separated from bark of Zanthoxylum clava. Modern pharmacology study showed that berberine has defined structure and is a monomer of traditional Chinese medicine. Berberine can be obtained from many sources and is used in clinics, with reliable pharmacological effects and various and unique mechanisms. At present, berberine can be synthesized by industrial biosynthesis. A series of derivatives can also be synthesized by structure modification, and the pharmacological activities of these derivatives have been tested.
VerwendenAntiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil
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