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15299-77-1

15299-77-1 Structure

15299-77-1 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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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