lycorenine
lycorenine Basic information
- Product Name:
- lycorenine
- Synonyms:
-
- lycorenine
- [2]Benzopyrano[3,4-g]indol-7-ol, 1,2,3,5,5a,7,11b,11c-octahydro-9,10-dimethoxy-1-methyl-,(5aR,7S,11bS,11cS)-
- 9,10-Dimethoxy-1-methyllycorenan-7α-ol
- (5aR,7S,11bS,11cS)-9,10-dimethoxy-1-methyl-3,5,5a,7,11b,11c-hexahydro-2H-isochromeno[3,4-g]indol-7-ol
- (5aR,7S,11bS,11cS)-1,2,3,5,5a,7,11b,11c-Octahydro-9,10-dimethoxy-1-methyl-[2]benzopyrano[3,4-g]indol-7-ol
- ycorenine
- lycorenine USP/EP/BP
- (7alpha)-9,10-dimethoxy-1-methyllycorenan-7-ol
- CAS:
- 477-19-0
- MF:
- C18H23NO4
- MW:
- 317.38
- Mol File:
- 477-19-0.mol
lycorenine Chemical Properties
- Melting point:
- 199-200℃
- Boiling point:
- 477.7±45.0 °C(Predicted)
- Density
- 1.28
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Cryst.
- pka
- 11.98±0.20(Predicted)
lycorenine Usage And Synthesis
Description
An alkaloid isolated from Lycoris radiata Herb. the base crystallizes from Me2CO in rhombic prisms and has [α]20D + 149.3°. The alkaloid yields crystalline salts and derivatives, e.g. the aurichloride decomposing at 116°C, platinichloride, also decomposing before melting at 210°C; picrate, m.p. 162°C (dec.); monoacetyl derivative, m.p. 185 _7°C. The diacetyl compound has been prepared although with some difficulty and under forcing conditions, m.p. 17 5-6°C. The alkaloid behaves as a pseudo-base giving an oxime hydrochloride which decomposes at 258°C. On catalytic hydrogenation it yields the dihydro-derivative, m.p. 175- 7°C and prolonged hydrogenation eventually forms deoxytetrahydrolycorenine, ClsH2S03N, m.p. 165-8°C although other compounds are also formed at the same time, e.g. C1sH27 0 2N, m.p. l65-7°C and ClsH2S03N, m.p. l20-3°C. The methiodide decomposes when heated at 260°C and on treatment with silver oxide forms two methine bases, of which the (±)-form has been isolated as the methiodide, m.p. 223°C (dec.). The complete structure has been determined primarily from the mass spectrum.
Uses
Lycorenine is an antibacterial agent extracted from the bulb of Lycoris radiata.
Definition
ChEBI: Lycorenine is an alkaloid.
target
Antifection
References
Kondo, Tomimura, Ishiwatari., J. Pharrn. Soc., Japan, 52, 51 (1932) Spectra: Inuka et aI., Tetrahedron Lett., 4745 (1966) Stereochemistry: Mizukami., Tetrahedron, 11,89 (1960)
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