Gynocardin
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| 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
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| Identifiers | |
3D model (JSmol)
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| KEGG | |
PubChem CID
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| 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).
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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
[edit]- ^ Power, Frederick Belding; Lees, Frederic Herbert (1905). "XLII.—Gynocardin, a new cyanogenetic glucoside". J. Chem. Soc., Trans. 87: 349–357. doi:10.1039/CT9058700349.
- ^ Coburn, Robert A.; Long, Louis (1966). "Gynocardin". The Journal of Organic Chemistry. 31 (12): 4312–4315. doi:10.1021/jo01350a550.
- ^ a b 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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