99-18-3 Usage
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 99-18-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 99-18:
(4*9)+(3*9)+(2*1)+(1*8)=73
73 % 10 = 3
So 99-18-3 is a valid CAS Registry Number.
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
99-18-3Relevant articles and documents
New flavonoid glycosides and cyanogenic glycosides from dracocephalum peregrinum
Fu, Peng,Zhao, Chun-Chao,Tang, Jian,Shen, Yun-Heng,Xu, Xi-Ke,Zhang, Wei-Dong
, p. 207 - 210 (2009)
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
Go, Mi-Ran,Kim, Hyeon-Jin,Yu, Jin,Choi, Soo-Jin
, p. 11432 - 11440 (2018/11/20)
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
Yashunsky, Dmitry V.,Kulakovskaya, Ekaterina V.,Kulakovskaya, Tatiana V.,Zhukova, Olga S.,Kiselevskiy, Mikhail V.,Nifantiev, Nikolay E.
, p. 460 - 474 (2015/12/23)
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.