Ranunculin

Last updated
Ranunculin
Ranunculin skeletal.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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 Yes check.svgY
    Key: TYWXNGXVSZRXNA-NVZSGMJQSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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 Protoanemonina.svg
Protoanemonin, the decomposition product of ranunculin

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References

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