Solanine

Not to be confused with Solanin.

α-Solanine
Names
IUPAC name
Solanid-5-en-3β-yl α-L-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside
Systematic IUPAC name
(2S,3R,4R,5R,6S)-2-{[(2R,3R,4S,5S,6R)-5-Hydroxy-6-(hydroxymethyl)-2-{[(2S,4aR,4bS,6aS,6bR,7S,7aR,10S,12aS,13aS,13bS)-4a,6a,7,10-tetramethyl-2,3,4,4a,4b,5,6,6a,6b,7,7a,8,9,10,11,12a,13,13a,13b,14-icosahydro-1H-naphtho[2′,1′:4,5]indeno[1,2-b]indolizin-2-yl]oxy}-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
Other names
α-Solanine; Solanin; Solatunine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.039.875 Edit this at Wikidata
UNII
  • InChI=1S/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3/t19-,20+,21-,23-,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39-,40+,41+,42-,43+,44-,45-/m0/s1 ☒N
    Key: ZGVSETXHNHBTRK-OTYSSXIJSA-N ☒N
  • InChI=1/C45H73NO15/c1-19-6-9-27-20(2)31-28(46(27)16-19)15-26-24-8-7-22-14-23(10-12-44(22,4)25(24)11-13-45(26,31)5)57-43-40(61-41-37(54)35(52)32(49)21(3)56-41)39(34(51)30(18-48)59-43)60-42-38(55)36(53)33(50)29(17-47)58-42/h7,19-21,23-43,47-55H,6,8-18H2,1-5H3/t19-,20+,21-,23-,24+,25-,26-,27+,28-,29+,30+,31-,32-,33+,34-,35+,36-,37+,38+,39-,40+,41+,42-,43+,44-,45-/m0/s1
    Key: ZGVSETXHNHBTRK-OTYSSXIJBP
  • C[C@H]1CC[C@@H]2[C@H]([C@H]3[C@@H](N2C1)C[C@@H]4[C@@]3(CC[C@H]5[C@H]4CC=C6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@@H]9[C@@H]([C@@H]([C@H]([C@@H](O9)C)O)O)O)C)C)C
Properties
C45H73NO15
Molar mass 868.06
Appearance white crystalline solid
Melting point 271 to 273 °C (520 to 523 °F; 544 to 546 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Solanine is a glycoalkaloid poison found in species of the nightshade family within the genus Solanum, such as the potato (Solanum tuberosum). It can occur naturally in any part of the plant, including the leaves, fruit, and tubers. Solanine has pesticidal properties, and it is one of the plant's natural defenses. Solanine was first isolated in 1820 from the berries of the European black nightshade (Solanum nigrum), after which it was named.[1] It belongs to the chemical family of saponins

  1. ^ Desfosses (1820). "Extrait d'une lettre de M. Desfosses, pharmacien, à Besançon, à M. Robiquet" [Extract of a letter from Mr. Desfosses, pharmacist in Besançon, to Mr. Robiquet]. Journal de Pharmacie. 2nd series (in French). 6: 374–376.