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
CAS Number
  • 644-69-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 390250 checkY
ECHA InfoCard 100.010.384 Edit this at Wikidata
PubChem CID
  • 441581
UNII
  • IBP7446K1O checkY
CompTox Dashboard (EPA)
  • DTXSID40982977 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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
Chemical compound

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

  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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