A cyanogenic glucoside
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(R)-Prunasin

Item No. 15959

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
αR-(β-D-glucopyranosyloxy)-benzeneacetonitrile
CAS Number
99-18-3
Molecular Formula
C14H17NO6
Formula Weight
295.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H](C#N)C2=CC=CC=C2)[C@@H]1O
InChi Code
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-/m1/s1
InChi Key
ZKSZEJFBGODIJW-MXNNCRBYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $103

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    1 mg

    $183

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    5 mg

    $602

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sánchez-Pérez, R., Belmonte, F.S., Borch, J., et al. Prunasin hydrolases during fruit development in sweet and bitter almonds. Plant Physiol. 158(4), 1916-1932 (2012).

    2. Mizushina, Y., Takahashi, N., Ogawa, A., et al. The cyanogenic glucoside, prunasin (D-mandelonitrile-β-D-glucoside), is a novel inhibitor of DNA polymerase β. J. Biochem. 126(2), 430-436 (1999).