Ranunculin

Ranunculin is an unstable glucoside found in plants of the buttercup family (Ranunculaceae). On maceration, for example when the plant is wounded, it is enzymatically broken down into glucose and the toxin protoanemonin.[1]

Protoanemonin, the decomposition product of ranunculin
Ranunculin
Names
IUPAC name
(5S)-5-[(β-D-Glucopyranosyloxy)methyl]furan-2(5H)-one
Systematic IUPAC name
(5S)-5-({[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)furan-2(5H)-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.384
UNII
  • InChI=1S/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1 checkY
    Key: TYWXNGXVSZRXNA-NVZSGMJQSA-N checkY
  • InChI=1/C11H16O8/c12-3-6-8(14)9(15)10(16)11(19-6)17-4-5-1-2-7(13)18-5/h1-2,5-6,8-12,14-16H,3-4H2/t5-,6+,8+,9-,10+,11+/m0/s1
    Key: TYWXNGXVSZRXNA-NVZSGMJQBP
  • C1=CC(=O)OC1COC2C(C(C(C(O2)CO)O)O)O
Properties
C11H16O8
Molar mass 276.241 g·mol−1
Melting point 141 to 142 °C (286 to 288 °F; 414 to 415 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

References
  1. Berger, Artur; Wachter, Helmut, eds. (1998). Hunnius Pharmazeutisches Wörterbuch (in German) (8 ed.). Walter de Gruyter Verlag. ISBN 3-11-015793-4.
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