Gynocardin

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Gynocardin
Gynocardin.svg
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
  • 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
  • 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
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).

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. [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]

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. 1 2 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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