Gynocardin

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;
CompTox Dashboard (EPA)	DTXSID30931818 ;
	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

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

^ 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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[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.

[Spencer-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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