ChemicalBook--->CAS DataBase List--->4684-32-6

4684-32-6

4684-32-6 Structure

4684-32-6 Structure
IdentificationBack Directory
[Name]

2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester
[CAS]

4684-32-6
[Synonyms]

Picrinin
Picrinine
5α-Epoxy-1
Vincaridine
GenericnaMe
Picrinine ,98%
DeacetyldeforMylpicraline
2-dihydroakuammilan-17-oic acid methyl ester
2α,5α-Epoxy-1,2-dihydroakuammilan-17-oic acid methyl ester
methyl (2alpha,5alpha,19E)-1,2-dihydro-2,5-epoxyakuammilan-1...
Methyl (2alpha,5alpha,15alpha,16xi,19E)-1,2-dihydro-2,5-epoxyakuammilan-17-oate
2H,12H-6,12A-Epoxy-2,7A-methanoindolo[2,3-A]quinolizine-14-carboxylic acid, 3-ethylidene-1,3,4,6,7,12B-hexahydro-, methyl ester, (2S,3E,6S,12ar,12bs)-
2H,12H-6,12a-Epoxy-2,7a-methanoindolo[2,3-a]quinolizine-14-carboxylic acid, 3-ethylidene-1,3,4,6,7,12b-hexahydro-, methyl ester, (2R,3E,6S,7aR,12aR,12bS,14R)-
Inchi=1/C20H22N2o3/C1-3-11-10-22-15-8-12(11)17(18(23)24-2)19-9-16(22)25-20(15,19)21-14-7-5-4-6-13(14)19/H3-7,12,15-17,21H,8-10H2,1-2H3/B11-3-/T12-,15+,16+,17,19,20+/m1/s
[Molecular Formula]

C20H22N2O3
[MOL File]

4684-32-6.mol
[Molecular Weight]

338.405
Chemical PropertiesBack Directory
[Melting point ]

222-224 °C
[Boiling point ]

501.1±50.0 °C(Predicted)
[density ]

1.38±0.1 g/cm3(Predicted)
[pka]

4.47±0.40(Predicted)
Hazard InformationBack Directory
[Description]

An Alstonia alkaloid obtained from A. scholaris R. Br., this base also occurs in Rauwolfia vornitora. It has [α]D - 47° (CHCI3). The ultraviolet spectrum in neutral solution (EtOH) has absorption maxima at 237 and 287 mil, while in acidic solution (perchloric acid), there are absorption maxima at 239, 244 and 305 mil. A methoxycarbonyl group, an alkyl group and an ether bridge are present in the molecule. The picrate is obtained as light yellow crystals with m.p. 172- 4°C (dec.) and the methiodide has m.p. 235-7°C.
[Uses]

Picrinine is a monoterpenoid indole alkaloid extracted from Ochrosia elliptica, displaing the enhancement of immunomodulatory activity and apaptosis inducing in the A549 cell lines.
[References]

Preparation:
Britten, Smith.,J. Chern. Soc., 3850 (1963)
Isolation:
Chatterjee et al., Tetrahedron Lett., 3633 (1965)
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