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23544-46-9

23544-46-9 Structure

23544-46-9 Structure
IdentificationBack Directory
[Name]

[4-(1,2,3,5,8,8a-Hexahydro-7-methylindolizin-6-yl)phenyl]β-D-glucopyranoside
[CAS]

23544-46-9
[Synonyms]

Ipalbine
4-(1,2,3,5,8,8a-Hexahydro-7-methylindolizin-6-yl)phenyl]β-D-glucopyranoside
[4-(1,2,3,5,8,8a-Hexahydro-7-methylindolizin-6-yl)phenyl]β-D-glucopyranoside
β-D-Glucopyranoside, 4-[(8aS)-1,2,3,5,8,8a-hexahydro-7-methyl-6-indolizinyl]phenyl
[Molecular Formula]

C21H29NO6
[MOL File]

23544-46-9.mol
[Molecular Weight]

391.46
Chemical PropertiesBack Directory
[Melting point ]

118 °C
[Boiling point ]

615.6±55.0 °C(Predicted)
[density ]

1.38±0.1 g/cm3(Predicted)
[pka]

12.83±0.70(Predicted)
Hazard InformationBack Directory
[Description]

This alkaloid, which is the O-~-D-glucoside of ipalbidine, also occurs in Ipomoea alba L. It is dextrorotatory with [α]23D + 32.5° (c 0.03, EtOH). The structure has been confirmed by the total synthesis from 2-methoxypyrroline and the methyl ester of acetylacetic acid.
[References]

Gourley et al., Chem. Commun., 709 (1969) Total synthesis: Wick, Bartlett, Dolphin., Helv. Chim. Acta., 54, 513 (1971)
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