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Solasodine

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-hexadecahydrospiro[naptho[2′,1′:4,5]indeno[2,1-b]furan-8,2′-piperidin]-2-ol
Other names
Purapuridine; Solancarpidine; Solanearpidine; Solanidine-S
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.341 Edit this at Wikidata
EC Number
  • 204-774-2
KEGG
UNII
  • 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/s1 checkY
    Key: KWVISVAMQJWJSZ-VKROHFNGSA-N checkY
  • O[C@@H]6C/C5=C/C[C@@H]1[C@H](CC[C@]3([C@H]1C[C@@H]4O[C@@]2(NC[C@H](C)CC2)[C@H]([C@H]34)C)C)[C@@]5(C)CC6
Properties
C27H43NO2
Molar mass 413.646 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae such as potatoes and tomatoes.[1] Solasonine and solamargine are glycoalkaloid derivatives of solasodine.[1] Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg.[2] 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.[3]

Uses

It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills, via a 16-DPA intermediate.[1]

See also

References

  1. ^ a b c 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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