99-18-3

(R)-Prunasin is a cyanogenic glucoside that is the precursor to amygdalin, a bitter component found in species of the genera Prunus and Olinia. It can be degraded to hydrogen cyanide, glucose, and benzaldehyde by the action of prunasin hydrolase and mandelonitrile lyase and possesses inhibitory effects on plant growth. (R)-Prunasin reportedly inhibits rat DNA polymerase β, which performs base excision repair required for DNA maintenance and replication, with an IC₅₀ value of 98 μM.

White Solid

Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair

ChEBI: (R)-prunasin is a prunasin.

This cyanogenic glucoside (FW = 295.29 g/mol; CAS 99-18-3), also known as D(R)-mandelonitrile-b-D-glucoside, is readily obtained from amygdalin and is found in the pits of Prunus serotina. Prunasin is soluble in water and will give rise to prulaurasin (i.e., the diastereoisomeric mixture of DL(RS)- mandelonitrile-b-D-glucoside [i.e., prunasin and sambunigrin]). Target(s): DNA-directed DNA polymerase; DNA polymerase b; and a,a trehalase.

[1] RAQUEL SáNCHEZ-PéREZ. Prunasin hydrolases during fruit development in sweet and bitter almonds.[J]. Plant Physiology, 2012, 158 4: 1916-1932. DOI: 10.1104/pp.111.192021
[2] Y MIZUSHINA. The cyanogenic glucoside, prunasin (D-mandelonitrile-beta-D-glucoside), is a novel inhibitor of DNA polymerase beta.[J]. Journal of biochemistry, 1999, 126 2: 430-436. DOI: 10.1093/oxfordjournals.jbchem.a022468