| Identification | Back Directory | [Name]
13,14-Dihydro-2',14β-dihydroxy-4'',5''-dimethoxylythran-12-one | [CAS]
15299-77-1 | [Synonyms]
Sinine
Lythridine
13,14-Dihydro-2',14β-dihydroxy-4'',5''-dimethoxylythran-12-one
20H-6,20-Methano-11,15-metheno-1H,8H-benzo[g]pyrido[2,1-d][1,5]oxaazacyclohexadecin-8-one, 2,3,4,4a,5,6,9,10-octahydro-10,14-dihydroxy-17,18-dimethoxy-, stereoisomer | [Molecular Formula]
C26H31NO6 | [MOL File]
15299-77-1.mol | [Molecular Weight]
453.53 |
| Chemical Properties | Back Directory | [Melting point ]
218-9°C | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 20 mg/ml; DMSO: 20 mg/ml; Ethanol: 1 mg/ml | [form ]
A crystalline solid |
| Hazard Information | Back Directory | [Description]
Both Heirnia rnyritifolia Cham. et Schl. and H. salicifolia Link & Otto yield this
macrocyc1ic alkaloid which may be crystallized from a mixture of AcOEt, MeOH
and light petroleum as glistening needles. Two somewhat different values for the
specific rotation have been recorded, viz. [α]25D - 174.2° (c 0.3325, CHC13) by
Blomster and [α]25D - 153.4° (c 0.3, CHCI3) by Douglas. The ultraviolet spectrum exhibits a broad absorption maximum at 292 mil and an inflexion at
250 mil. Two methoxyl groups, a secondary and a phenolic hydroxyl group are
present. The hydrochloride yields colourless crystals from MeOH, m.p. 330°C
(dec.). The structure has been determined mainly from the infrared and mass
spectra. | [References]
Douglas et ai., L/oydia, 27, 25 (1964)
Blomster, Schwarting, Bobbitt., ibid, 27, 15 (1964)
Absolute configuration:
Chu et ai., Chern. Ind., 1795 (1966)
Mass spectrum:
Appel, Achenbach., Tetrahedron Lett., 5789 (1966)
Structure:
Ferris, Boyce, Briner., J. Arner. Chern. Soc., 93, 2942 (1971)
Ferris et ai., ibid, 93, 2963 (1971) |
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