Gynocardin

{{Chembox  | ImageFile = Gynocardin.svg | ImageSize = 200px | ImageAlt =  | IUPACName = (1''R'',4''S'',5''R'')-4,5-Dihydroxy-1-[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclopent-2-ene-1-carbonitrile | OtherNames =  | Section1 = {{Chembox Identifiers | CASNo = 14332-17-3 | ChEBI = 5578 | ChemSpiderID = 390192 | PubChem = 441466 | KEGG = C08331 | StdInChI=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 | StdInChIKey = 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 }} | Section2 = {{Chembox Properties | C = 12 | H = 17 | N = 1 | O = 8 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}

'''Gynocardin''' is a chemical compound with the molecular formula {{chem2|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.<ref>{{cite journal | doi = 10.1039/CT9058700349 | title = XLII.—Gynocardin, a new cyanogenetic glucoside | date = 1905 | last1 = Power | first1 = Frederick Belding | last2 = Lees | first2 = Frederic Herbert | journal = J. Chem. Soc., Trans. | volume = 87 | pages = 349–357 }}</ref><ref>{{cite journal | doi = 10.1021/jo01350a550 | title = Gynocardin | date = 1966 | last1 = Coburn | first1 = Robert A. | last2 = Long | first2 = Louis | journal = The Journal of Organic Chemistry | volume = 31 | issue = 12 | pages = 4312–4315 }}</ref> It has since been found in a variety of other plants, including those in the genus ''Passiflora'' (passionflowers).<ref name=Spencer>{{cite journal | doi = 10.1055/s-2007-969732 | title = Gynocardin from ''Passiflora'' | date = 1984 | last1 = Spencer | first1 = Kevin | last2 = Seigler | first2 = David | journal = Planta Medica | volume = 50 | issue = 4 | pages = 356–357 | pmid = 17340327 }}</ref>

Gynocardin may contribute to the toxicity of plants that contain it because, like other cyanogenic glycosides, cyanide is formed upon its hydrolysis.<ref name=Spencer/>

==References== {{reflist}}

Category:Cyanogenic glycosides Category:Cyclopentenes