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-beta-D-glucoside
Identifiers
CAS Number	99-18-3
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17396
ChemSpider	106360
ECHA InfoCard	100.002.489
EC Number	202-738-0
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
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.^[1] It is also found in leaves and stems of Olinia ventosa, O. radiata, O. emarginata and O. rochetiana^[2] or in Acacia greggii.

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

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.

↑ Sanchez-Perez, R.; Belmonte, F. S.; Borch, J.; Dicenta, F.; Møller, B. L.; Jørgensen, K. (2012). "Prunasin Hydrolases during Fruit Development in Sweet and Bitter Almonds". Plant Physiology. 158 (4): 1916–32. doi:10.1104/pp.111.192021. PMC 3320195. PMID 22353576.
↑ Nahrstedt, Adolf; Rockenbach, Jürgen (1993). "Occurrence of the cyanogenic glucoside prunasin and II corresponding mandelic acid amide glucoside in Olinia species (oliniaceae)". Phytochemistry. 34 (2): 433. doi:10.1016/0031-9422(93)80024-M.

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