Gynocardin

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

Quick facts Names, Identifiers ...

Gynocardin

Names
IUPAC name (1R,4S,5R)-4,5-Dihydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile
Identifiers
CAS Number	14332-17-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5578
ChemSpider	390192
KEGG	C08331
PubChem CID	441466
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/s1 Key: HASDUOHKNMHNJA-GDLVSTOPSA-N
SMILES C1=C[C@]([C@@H]([C@H]1O)O)(C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
Chemical formula	C12H17NO8
Molar mass	303.267 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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It was first isolated from Gynocardia odorata, from which it gets it name, and characterized in 1905.^[1][2] It has since been found in a variety of other plants, including those in the genus Passiflora (passionflowers).^[3]

Gynocardin may contribute to the toxicity of plants that contain it because, like other cyanogenic glycosides, cyanide is formed upon its hydrolysis.^[3]