| Identification | Back Directory | [Name]
PRUNASIN | [CAS]
99-18-3 | [Synonyms]
Prunacin
PRUNASIN
d-prunasin
(r)-prunasin
Noguro Sakura
(r)-benzeneacetonitril
D-MANDELONITRILE B-D-GLUCOSIDE
D-Mandelonitrile β-D-glucoside
D-MANDELONITRILE-BETA-D-GLUCOSIDE
[(αR)-α-Cyanobenzyl]β-D-glucopyranoside
PENTAMETHYL-6-HYDROXYCHROMAN, 2,2,5,7,8-(RG)
(R)-α-(β-D-Glucopyranosyloxy)benzeneacetonitrile
(R)-(beta-D-glucopyranosyloxy)phenylacetonitrile
(αR)-α-(β-D-Glucopyranosyloxy)-α-phenylacetonitrile
Benzeneacetonitrile, a-(b-D-glucopyranosyloxy)-, (aR)-
Benzeneacetonitrile, α-(β-D-glucopyranosyloxy)-, (αR)-
(r)-alpha-(beta-d-glucopyranosyloxy)benzene-acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-ethanenitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methylol-tetrahydropyran-2-yl]oxy-acetonitrile | [EINECS(EC#)]
202-738-0 | [Molecular Formula]
C14H17NO6 | [MDL Number]
MFCD00049232 | [MOL File]
99-18-3.mol | [Molecular Weight]
295.29 |
| Chemical Properties | Back Directory | [Melting point ]
138-148°C | [Boiling point ]
527.0±50.0 °C(Predicted) | [density ]
1.45±0.1 g/cm3(Predicted) | [storage temp. ]
Hygroscopic, -20°C Freezer, Under Inert Atmosphere | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
12.71±0.70(Predicted) | [color ]
White to off-white | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
(R)-Prunasin is a cyanogenic glucoside that is the precursor to amygdalin, a bitter component found in species of the genera Prunus and Olinia.1 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.1 (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.2 | [Chemical Properties]
White Solid | [Uses]
Used in the synthesis of cyanogen glycoside. A component of antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair | [Definition]
ChEBI: (R)-prunasin is a prunasin. | [Enzyme inhibitor]
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. |
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