Chaconine

Chaconine

Names
IUPAC name beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(6-deoxy-alpha-L-mannopyranosyl-(1-4))-
Identifiers
CAS Number	20562-03-2
Beilstein Reference	77396
ChemSpider	391274
Jmol interactive 3D	Image
PubChem	442971
InChI InChI=1S/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,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: TYNQWWGVEGFKRU-AJDPQWBVSA-N InChI=1/C45H73NO14/c1-19-7-10-28-20(2)31-29(46(28)17-19)16-27-25-9-8-23-15-24(11-13-44(23,5)26(25)12-14-45(27,31)6)57-43-40(60-42-37(53)35(51)33(49)22(4)56-42)38(54)39(30(18-47)58-43)59-41-36(52)34(50)32(48)21(3)55-41/h8,19-22,24-43,47-54H,7,9-18H2,1-6H3/t19-,20+,21-,22-,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: TYNQWWGVEGFKRU-AJDPQWBVBS
SMILES O([C@H]8[C@H](O[C@@H]4C/C3=C/C[C@H]2[C@@H]5C[C@@H]1N6[C@@H]([C@@H](C)[C@@H]1[C@@]5(C)CC[C@@H]2[C@@]3(C)CC4)CC[C@H](C)C6)O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@@H]8O)[C@@H]9O[C@H]([C@H](O)[C@@H](O)[C@H]9O)C
Properties
Chemical formula	C45H73NO14
Molar mass	852.07 g·mol^−1
Melting point	243 °C (469 °F; 516 K)
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

α-Chaconine is a steroidal glycoalkaloid that occurs in plants of the Solanaceae family. It is a natural toxicant produced in green potatoes and gives the potato a bitter taste.^[1] Tubers produce this glycoalkaloid in response to stress, providing the plant with insecticidal and fungicidal properties.^[1]

See also

• Solamargine
• Solanine

References

1. Kuiper-Goodman, T. and Nawrot, P.S. "Toxin profile:Solanine and Chaconine" IPCS, INCHEM