| Identification | Back Directory | [Name]
lycorenine | [CAS]
477-19-0 | [Synonyms]
ycorenine
lycorenine
lycorenine USP/EP/BP
9,10-Dimethoxy-1-methyllycorenan-7α-ol
(7alpha)-9,10-dimethoxy-1-methyllycorenan-7-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
[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)- | [Molecular Formula]
C18H23NO4 | [MDL Number]
MFCD09954183 | [MOL File]
477-19-0.mol | [Molecular Weight]
317.38 |
| Chemical Properties | Back Directory | [Melting point ]
199-200℃ | [density ]
1.28 | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Cryst. |
| Hazard Information | Back Directory | [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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