125781-60-4

Basic information

• Product Name: (S)-3-HYDROXYMANDELONITRILE
• Synonyms: (S)-3-HYDROXYMANDELONITRILE
• CAS NO: 125781-60-4
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• Mol File: 125781-60-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-HYDROXYMANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-HYDROXYMANDELONITRILE(125781-60-4)
• EPA Substance Registry System: (S)-3-HYDROXYMANDELONITRILE(125781-60-4)

Safety Data

• Hazardous Substances Data: 125781-60-4(Hazardous Substances Data)

Usage

General Description

(S)-3-Hydroxymandelonitrile is a complex organic compound featuring a hydroxy group, a cyanide group and a phenyl ring. This chemical is considered as a significant component in cyanogenic glycosides, which are naturally occurring toxin substances found in numerous plants and certain insects. Such a presence aids in plant defense mechanism against herbivores. Humans and animals can consume such plants, leading to potential health issues, like cyanide poisoning if consumed extensively. Yet, (S)-3-Hydroxymandelonitrile possesses considerable pharmaceutical value connected with developing treatments for cancer, hypertension, and certain eye conditions. The selection and dosage should be monitored cautiously due to the risk of cyanide poisoning.

Upstream product

• 74-90-8 hydrogen cyanide 
• 100-83-4 meta-hydroxybenzaldehyde 

Relevant articles and documents

ENZYME-CATALYZED SYNTHESIS OF (S)-CYANOHYDRINS AND SUBSEQUENT HYDROLYSIS TO (S)-α-HYDROXY-CARBOXYLIC ACIDS

(S)-Cyanohydrins 2 are obtained with high enantioselectivity from aromatic aldehydes and HCN in the presence of (S)-oxynitrilase (E.C.4.1.2.11).Acid-catalyzed hydrolysis of the cyanohydrins 2 affords the corresponding (S)-α-hydroxy carboxylic acids 3 without racemization.

Asymmetric Hydrocyanation of a Range of Aromatic and Aliphatic Aldehydes

A range of aryl, alkyl and heterocyclic aldehydes have been treated with hydrogen cyanide in the presence of the 'Inoue' catalyst, (R,R)- or (S,S)-cyclo.Most aryl aldehydes with electron-donating substituents in the m-or p-positions give high enantiomeric excess (e.e) values (>=80percent) but aryl aldehydes with strong electron-withdrawing substituents gave moderate e.e. values (=50percent).These moderate values are believed to be due to partial racemization of the product cyanohydrins in the presence of the mildly basic catalyst.In contrast to the reactions of aryl aldehydes, reactions of alkyl aldehydes and of ketones gave low e.e. values (=30percent) and an explanation is proposed.