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Ranunculin

From Wikipedia, the free encyclopedia
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 Edit this at Wikidata
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).
checkY verify (what is checkY☒N ?)

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

References

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