Prunasin

Names

[ CAS No. ]:
99-18-3

[ Name ]:
Prunasin

[Synonym ]:
Prunasin
(2S)-(β-D-Glucopyranosyloxy)(phenyl)acetonitrile
(2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyacetonitrile
D-Prunasin
Benzeneacetonitrile, α-(β-D-glucopyranosyloxy)-, (αS)-

Biological Activity

[Description]:

Prunasin is a inhibitor of DNA Polymerase β[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

[References]

[1]. Mizushina Y, et al. The cyanogenic glucoside, prunasin (D-mandelonitrile-beta-D-glucoside), is a novel inhibitor of DNA polymerase beta. J Biochem. 1999;126(2):430-436.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
527.0±50.0 °C at 760 mmHg

[ Melting Point ]:
138-148ºC

[ Molecular Formula ]:
C₁₄H₁₇NO₆

[ Molecular Weight ]:
295.29

[ Flash Point ]:
272.5±30.1 °C

[ Exact Mass ]:
295.105591

[ PSA ]:
123.17000

[ LogP ]:
-0.92

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.621

[ Storage condition ]:
Hygroscopic, -20°C Freezer, Under Inert Atmosphere

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UL3420000

CHEMICAL NAME :: Prunasin

CAS REGISTRY NUMBER :: 99-18-3

BEILSTEIN REFERENCE NO. :: 0091509

LAST UPDATED :: 199709

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C14-H17-N-O6

MOLECULAR WEIGHT :: 295.32

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 177 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 215,1513,1982

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301-H360

[ Precautionary Statements ]:
P201-P301 + P310-P308 + P313

[ Hazard Codes ]:
T

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-36/37/39

[ RIDADR ]:
UN 2811 6.1 / PGIII

[ RTECS ]:
UL3420000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Chromatographic determination of cyanoglycosides prunasin and amygdalin in plant extracts using a porous graphitic carbon column.

J. Agric. Food Chem. 50(24) , 6960-3, (2002)

The determination of cyanogenic compounds in plants is often performed by HPLC. However, in this analysis, interferences due to compounds in the matrix, such as tannins and other pigments, are encount...

Larvae of the fall webworm, Hyphantria cunea, inhibit cyanogenesis in Prunus serotina.

J. Immunol. Methods 211 , 671-7, (2008)

The larvae of the fall webworm, Hyphantria cunea (Dru.), though vulnerable to cyanide poisoning, consume the cyanogenic leaves of black cherry, Prunus serotina, without apparent harm. The cyanide cont...

Generation of primary amide glucosides from cyanogenic glucosides

Phytochemistry 70(3) , 388-93, (2009)

The conversion of the cyanogenic glucoside prunasin into the corresponding prunasinamide has been observed in the leaves of Olinia ventosa and other prunasin-containing species only if reactive oxygen...