Solanocapsine

Solanocapsine is a toxic steroidal alkaloid from Solanum pseudocapsicum (Jerusalem cherry).

Solanocapsine
Names
IUPAC name
3β-Amino-16,23-epoxy-16α,28-seco-5α-solanidan-23β-ol
Systematic IUPAC name
(2S,4aS,3bS,6aS,6bR,7S,7aR,10R,11aS,12aR,13aS,13bR,15aS)-2-Amino-4a,6a,7,10-tetramethyldocosahydronaphtho[2′′,1′′:4′,5′]indeno[1′,2′:5,6]pyrano[3,2-b]pyridin-11a(1H)-ol
Other names
3β-Amino-22,26-epimino-16α,23-epoxy-5α,22αH,25βH-cholestan-23β-ol; (3β,5α,16α,22α,23β,25β)-3-Amino-16,23-epoxy-16,28-secosolanidan-23-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C27H46N2O2/c1-15-13-27(30)24(29-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(28)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,29-30H,5-14,28H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22-,23+,24-,25+,26+,27+/m1/s1 ☒N
    Key: ZPTJKUUQUDRHTL-QAQRTNARSA-N ☒N
  • InChI=1/C27H46N2O2/c1-15-13-27(30)24(29-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(28)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,29-30H,5-14,28H2,1-4H3/t15-,16+,17+,18+,19-,20+,21+,22-,23+,24-,25+,26+,27+/m1/s1
    Key: ZPTJKUUQUDRHTL-QAQRTNARBX
  • C[C@@H]1C[C@]2([C@@H]([C@H]([C@H]3[C@H](O2)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC[C@@H]6[C@@]5(CC[C@@H](C6)N)C)C)C)NC1)O
Properties
C27H46N2O2
Molar mass 430.666
Appearance long flat colorless prisms (ethanol-H2O)[1]
Melting point 222 °C (432 °F; 495 K)[1] 216-217 °C [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Barger, L. G.; Fraenkel-Conrat, H. L. (1936). "337. Alkaloids from Solanum pseudocapsicum, L.". Journal of the Chemical Society. 1936: 1537–1542. doi:10.1039/JR9360001537.
  2. Schlittler, E.; Uehlinger, H. (1952). "Über das Sterinalkaloid Solanocapsin". Helvetica Chimica Acta (in German). 35 (6): 2034–2044. doi:10.1002/hlca.19520350633.
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