PRUNASIN Chemical Properties

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

InChI

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+/s3

InChIKey

ZKSZEJFBGODIJW-OAWZEMCWNA-N

SMILES

O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@H](C1C=CC=CC=1)C#N |&1:1,2,3,5,7,12,r|

Safety Information

Hazard Codes 

T

Risk Statements 

36/37/38-25-60

Safety Statements 

26-36/37/39-61-45

RIDADR 

UN 2811 6.1 / PGIII

WGK Germany 

3

RTECS 

UL3420000

PRUNASIN Usage And Synthesis

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. 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.

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.

References

[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

PRUNASIN(99-18-3)Related Product Information

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• hydroxygenkwanin
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• PRUNASIN
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• PRUNASIN(RG)
• AMYGDALIN TRIHYDRATE
• PHENYL-[3,4,5-TRIHYDROXY-6-(3,4,5-TRIHYDROXY-6-HYDROXYMETHYL-TETRAHYDRO-PYRAN-2-YLOXYMETHYL)-TETRAHYDRO-PYRAN-2-YLOXY]-ACETONITRILE
• HOLOCALIN
• prunasin hydrolase