27495-40-5

Basic information

• Product Name: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one
• Synonyms: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one;Protostemonine;(5Z)-5-[(1S,3aR,8S,10aS,10bR)-Decahydro-1-methyl-8-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-methoxy-3-methyl-2(5H)-furanone;2(5H)-Furanone,5-[(1S,3aR,8S,10aS,10bR)-decahydro-1-Methyl-8-[(2S,4S)-tetrahydro-4-Methyl-5-oxo-2-furanyl]-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-2-ylidene]-4-Methoxy-3-Methyl-,(5Z)-;(3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]
• CAS NO: 27495-40-5
• Molecular Formula: C23H31NO6
• Molecular Weight: 417.499
• Product Categories: reagent;standard substance
• Mol File: 27495-40-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 172℃
• Boiling Point: 594.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.27
• Refractive Index: 1.576
• PKA: 8.77±0.60(Predicted)
• CAS DataBase Reference: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one(27495-40-5)
• EPA Substance Registry System: (3S,5S)-5-[(1S,2Z,3aβ,10aα,10bα)-Decahydro-2-(2,5-dihydro-3-methoxy-4-methyl-5-oxofuran-2-ylidene)-1α-methyl-2H-furo[3,2-c]pyrrolo[1,2-a]azepin-8α-yl]-4,5-dihydro-3-methylfuran-2(3H)-one(27495-40-5)

Safety Data

• Hazardous Substances Data: 27495-40-5(Hazardous Substances Data)

Usage

Description

The roots of Sternona japonica contain this complex alkaloid which forms colourless crystals from MeOH containing solvent of crystallization. The base is dextrorotatory with [α]D + 147.8° and the ultraviolet spectrum shows a broad absorption maximum at 305 m/J.. The picrolonate has been prepared as yellow needles, m.p. 237°C. The structure given above is based upon X-ray crystallo_x0002_graphic analysis of the MeOH solvate and on the already established configuration of Stemonine (q.v.).

Uses

Protostemonine is an alkaloid which provided protective effects of protostemonine in LPS/GalN-induced acute liver failure.

References

Kondo, Satomi.,J. Pharrn. Soc., Japan, 67, 182, 185, 188 (1947) Structure: Irie et al., Chern. Pharrn. Bull., 21, 451 (1973)

InChI:InChI=1/C23H31NO6/c1-11-10-17(29-22(11)25)14-7-8-15-18-12(2)20(28-16(18)6-5-9-24(14)15)21-19(27-4)13(3)23(26)30-21/h11-12,14-18H,5-10H2,1-4H3/b21-20-/t11-,12-,14-,15-,16+,17-,18+/m0/s1

Downstream Products

• 27498-90-4 stemonine