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Gynocardin

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Gynocardin
Names
IUPAC name (1R,4S,5R)-4,5-Dihydroxy-1-oxycyclopent-2-ene-1-carbonitrile
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C12H17NO8/c13-4-12(2-1-5(15)10(12)19)21-11-9(18)8(17)7(16)6(3-14)20-11/h1-2,5-11,14-19H,3H2/t5-,6+,7+,8-,9+,10+,11-,12+/m0/s1Key: HASDUOHKNMHNJA-GDLVSTOPSA-N
SMILES
  • C1=C((1O)O)(C#N)O2((((O2)CO)O)O)O
Properties
Chemical formula C12H17NO8
Molar mass 303.267 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Gynocardin is a chemical compound with the molecular formula C12H17NO8. It is classified as a cyanogenic glycoside.

It was first isolated from Gynocardia odorata, from which it gets it name, and characterized in 1905. It has since been found in a variety of other plants, including those in the genus Passiflora (passionflowers).

Gynocardin may contribute to the toxicity of plants that contain it because, like other cyanogenic glycosides, cyanide is formed upon its hydrolysis.

References

  1. Power, Frederick Belding; Lees, Frederic Herbert (1905). "XLII.—Gynocardin, a new cyanogenetic glucoside". J. Chem. Soc., Trans. 87: 349–357. doi:10.1039/CT9058700349.
  2. Coburn, Robert A.; Long, Louis (1966). "Gynocardin". The Journal of Organic Chemistry. 31 (12): 4312–4315. doi:10.1021/jo01350a550.
  3. ^ Spencer, Kevin; Seigler, David (1984). "Gynocardin from Passiflora". Planta Medica. 50 (4): 356–357. doi:10.1055/s-2007-969732. PMID 17340327.
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