Prunasin

Prunasin

Chemical structure of 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-beta-D-glucoside
Identifiers
CAS Number	99-18-3
ChEBI	CHEBI:17396
ChemSpider	106360
EC Number	202-738-0
Jmol 3D model	Interactive image
KEGG	C00844
PubChem	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
Vapor pressure	{{{value}}}
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 glucoside related to amygdalin.

Natural occurrences

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 or in Acacia greggii.

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

Metabolism

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.