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Solasodine

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Solasodine
Names
IUPAC name (22R,25R)-Spirosol-5α-en-3β-ol
Systematic IUPAC name (2S,2′R,4aR,4bS,5′R,6aS,6bR,7S,9aS,10aS,10bS)-4a,5′,6a,7-Tetramethyl-1,2,3,4,4a,4b,5,6,6a,6b,7,9a,10,10a,10b,11-hexadecahydrospiroindenofuran-8,2′-piperidin]-2-ol
Other names Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.341 Edit this at Wikidata
EC Number
  • 204-774-2
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C27H43NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h5,16-17,19-24,28-29H,6-15H2,1-4H3/t16-,17+,19+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1Key: KWVISVAMQJWJSZ-VKROHFNGSA-N
SMILES
  • O6C/C5=C/C1(CC3(1C4O2(NC(C)CC2)(34)C)C)5(C)CC6
Properties
Chemical formula C27H43NO2
Molar mass 413.646 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. A 2013 literature survey found that various studies have indicated that solasodine may have diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and/or various other effects on central nervous system.

Uses

It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate.

See also

References

  1. ^ Everist, S.L. (1981). Poisonous Plants of Australia. Angus & Robertson. ISBN 978-0-207-14228-4.
  2. Kinghorn, A.D. (2010). "Toxins and Teratogens of the Solanaceae and Liliaceae". Toxic plants. Society for Economic Botany, Columbia University Press. pp. 75–76. ISBN 978-0231515689.
  3. Patel, Kanika; Singh, Ravi B.; Patel, Dinesh K. (2013). "Medicinal significance, pharmacological activities, and analytical aspects of solasodine: A concise report of current scientific literature". Journal of Acute Disease. 2 (2): 92–98. doi:10.1016/S2221-6189(13)60106-7.


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