99-18-3

Basic information

• Product Name: PRUNASIN
• Synonyms: D-Mandelonitrile β-D-glucoside;(R)-α-(β-D-Glucopyranosyloxy)benzeneacetonitrile;(αR)-α-(β-D-Glucopyranosyloxy)-α-phenylacetonitrile;[(αR)-α-Cyanobenzyl]β-D-glucopyranoside;Prunacin;(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
• CAS NO: 99-18-3
• Molecular Formula: C₁₄H₁₇NO₆
• Molecular Weight: 295.29
• EINECS: 202-738-0
• Product Categories: Miscellaneous Natural Products;Aromatics;Carbohydrates & Derivatives;Chiral Reagents
• Mol File: 99-18-3.mol
• Article Data: 9

Chemical Properties

• Melting Point: 138-148°C
• Boiling Point: 527°Cat760mmHg
• Flash Point: 272.5°C
• Appearance: /
• Density: 1.45g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• PKA: 12.71±0.70(Predicted)
• CAS DataBase Reference: PRUNASIN(CAS DataBase Reference)
• NIST Chemistry Reference: PRUNASIN(99-18-3)
• EPA Substance Registry System: PRUNASIN(99-18-3)

Safety Data

• Hazard Codes: T
• 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
• Hazardous Substances Data: 99-18-3(Hazardous Substances Data)

Usage

Description

PRUNASIN, also known as (R)-Prunasin, is a cyanogenic glucoside that serves as 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. PRUNASIN possesses inhibitory effects on plant growth and reportedly inhibits rat DNA polymerase β, which performs base excision repair required for DNA maintenance and replication, with an IC50 value of 98 μM. It is a white solid in its chemical form.

Uses

Used in the Synthesis of Cyanogen Glycosides:
PRUNASIN is used as a precursor in the synthesis of cyanogen glycosides, which are compounds containing a cyano group attached to a glycosidic moiety. These glycosides are of interest in various chemical and biological applications.
Used in Personal Care Products:
PRUNASIN is used as an ingredient in antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair conditioners. Its inclusion in these products is due to its potential antimicrobial and astringent properties, which can contribute to the effectiveness of personal care formulations.
Used in Pharmaceutical Applications:
Due to its inhibitory effects on plant growth and its ability to inhibit rat DNA polymerase β, PRUNASIN may have potential applications in the development of pharmaceuticals, particularly in areas related to DNA repair mechanisms and plant growth regulation.
Used in Chemical Research:
As a cyanogenic glucoside, PRUNASIN is also used in chemical research to study the properties and reactions of cyanogenic compounds, which can provide insights into the development of new chemical processes and applications.

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.

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+/m0/s1

Upstream product

• 29883-15-6 amygdalin 
• 100-52-7 benzaldehyde 
• 151649-54-6 (R)-α-(β-D-glucopyranosyloxy)phenylacetamide 
• 1169800-49-0 (2R)-β-D-(6-O-acetyl)-glucosyl-2-phenylacetonitrile 
• 207512-68-3 (R)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy(phenyl)acetamide 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 4358-86-5 (2R)-mandelamide 
• 60981-47-7 (2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile 
• 100-63-0 phenylhydrazine 

Downstream Products

• 60981-47-7 (2R)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile 
• 100-52-7 benzaldehyde 
• 611-71-2 MANDELIC ACID 
• 151649-54-6 (R)-α-(β-D-glucopyranosyloxy)phenylacetamide 
• 99-19-4 (2S)-2-(β-D-glucopyranosyloxy)phenylacetonitrile 

Relevant articles and documents

New flavonoid glycosides and cyanogenic glycosides from dracocephalum peregrinum

Separation of ethyl acetate fractionation of Dracocephalum peregrinum afforded three new flavonoid glucosides (1-3), and a new cyanogenic glucoside (4). Their structures were elucidated based on HR-electron spray ionization (ESI)-MS, EI-MS, UV, IR, 1D-, a

Toxicity and Toxicokinetics of Amygdalin in Maesil (Prunus mume) Syrup: Protective Effect of Maesil against Amygdalin Toxicity

Maesil (Prunus mume, green plum)-based products have been widely used in Asian cooking, which may contain amygdalin enzymatically converted to hydrogen cyanide after oral ingestion. In this study, the toxicity of Maesil syrups matured with and without Mae

Synthesis and Biological Evaluation of Cyanogenic Glycosides

An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.