Prunasin

Prunasin

Names
IUPAC name (2R)-2-Phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
Other names (R)-Prunasin D-Prunasin D-Mandelonitrile-β-D-glucoside
Identifiers
CAS Number	99-18-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17396
ChemSpider	106360
ECHA InfoCard	100.002.489
EC Number	202-738-0
KEGG	C00844
PubChem CID	119033
InChI InChI=1S/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1 Key: ZKSZEJFBGODIJW-GMDXDWKASA-N InChI=1/C14H17NO6/c15-6-9(8-4-2-1-3-5-8)20-14-13(19)12(18)11(17)10(7-16)21-14/h1-5,9-14,16-19H,7H2/t9-,10+,11+,12-,13+,14+/m0/s1 Key: ZKSZEJFBGODIJW-GMDXDWKABY
SMILES C1=CC=C(C=C1)[C@H](C#N)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
Properties
Chemical formula	C14H17NO6
Molar mass	295.29 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

Prunasin is a cyanogenic glycoside related to amygdalin.

Prunasin is found in species in the genus Prunus such as Prunus japonica or P. maximowiczii and in bitter almonds. It is also found in leaves and stems of Olinia ventosa, O. radiata, O. emarginata and O. rochetiana and in Acacia greggii.

It is also found in dandelion coffee, a coffee substitute.

Prunasin is hydrolyzed to produce hydrogen cyanide. Plants containing prunasin may therefore be toxic to animals, particularly ruminants.

Prunasin beta-glucosidase is an enzyme that uses (R)-prunasin and H₂O to produce D-glucose and mandelonitrile.

Amygdalin beta-glucosidase is an enzyme that uses (R)-amygdalin and H₂O to produce (R)-prunasin and D-glucose.