Vicianin

Vicianin
Names
	IUPAC name (2R)-2-Phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
	Other names (R)-Vicianin; 6-O-Arabinopyranosylglucopyranoside; β-Vicianoside
Identifiers
CAS Number	155-57-7 ;
3D model (JSmol)	Interactive image;
PubChem CID	656493;
UNII	CQU61CXY3D ;
CompTox Dashboard (EPA)	DTXSID70935113 ;
	SMILES C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H](C#N)C3=CC=CC=C3)O)O)O)O)O)O;
Properties
Chemical formula	C19H25NO10
Molar mass	427.406 g·mol−1
Related compounds
Related compounds	amygdalin
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

The enzyme vicianin beta-glucosidase uses (R)-vicianin and H₂O to produce mandelonitrile and vicianose. It is found in seeds of Vicia angustifolia.[1]

Vicianin is a cyanogenic disaccharide.

References

Ahn, Y. O.; Saino, H.; Mizutani, M.; Shimizu, B.-i.; Sakata, K. (2007). "Vicianin hydrolase is a novel cyanogenic beta-glycosidase specific to beta-vicianoside (6-O-alpha-L-arabinopyranosyl-beta-D-glucopyranoside) in seeds of Vicia angustifolia". Plant and Cell Physiology. 48 (7): 938. doi:10.1093/pcp/pcm065. PMID 17548373.

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