lycorenine

lycorenine Structure
CAS No.
477-19-0
Chemical Name:
lycorenine
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)-
CBNumber:
CB91377212
Molecular Formula:
C18H23NO4
Molecular Weight:
317.38
MOL File:
477-19-0.mol
Modify Date:
2024/8/5 20:55:42

lycorenine 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 Chemical Properties,Uses,Production

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.

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)

lycorenine Preparation Products And Raw materials

Raw materials

Preparation Products

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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 477-19-0