99-19-4

Usage

Uses

Used in Chemical Synthesis:
(S)-Prunasin is used as a key component in the synthesis of cyanogen glycoside, a class of compounds with potential applications in various fields.
Used in Personal Care Industry:
(S)-Prunasin is used as an active ingredient in a wide range of personal care products, including antiperspirants, deodorants, body soaps, shampoos, hair rinses, and hair relaxers. Its inclusion in these products is attributed to its ability to provide effective results and enhance the overall performance of the formulations.

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-/m1/s1

Upstream product

• 99-18-3 prunasin 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 60981-44-4 (2S)-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenylacetonitrile 

Relevant academic research and scientific papers

General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides

An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.

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.

Synthesis and Characterisation of α-Glycosyloxyamides Derived from Cyanogenic Glycosides

Introduction - After exposure to oxidative stress, the leaves of some cyanogenic plants contain primary α-glycosyloxyamides with structures corresponding to their original cyanogenic glycosides.Objectives - The aim of this study was to prepare such amides

PRUNASIN-6'-MALONATE, A CYANOGENIC GLUCOSIDE FROM MERREMIA DISSECTA

The cyanogenic glucosides prunasin and 6'-O-malonylprunasin have been isolated from the leaves of Merremia dissecta.Malonylprunasin is the first example of a malonyl conjugate of the cyanogenic glycosides. - Keywords: Merremia dissecta; Convolvulaceae; prunasin, malonylprunasin; cyanogenesis.