71807-09-5

Basic information

• Product Name: (S)-4-HYDROXYMANDELONITRILE
• Synonyms: (S)-4-HYDROXYMANDELONITRILE
• CAS NO: 71807-09-5
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• Mol File: 71807-09-5.mol

Chemical Properties

• Boiling Point: 366.0±27.0 °C(Predicted)
• Appearance: /
• Density: 1.327±0.06 g/cm3(Predicted)
• PKA: 9.35±0.26(Predicted)
• CAS DataBase Reference: (S)-4-HYDROXYMANDELONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-HYDROXYMANDELONITRILE(71807-09-5)
• EPA Substance Registry System: (S)-4-HYDROXYMANDELONITRILE(71807-09-5)

Safety Data

• Hazardous Substances Data: 71807-09-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-Hydroxymandelonitrile is used as a key intermediate in the synthesis of semisynthetic opioids and other pharmaceuticals, due to its unique chemical structure and properties.
Used in Anticancer Research:
(S)-4-Hydroxymandelonitrile is studied for its potential anticancer properties, as it may exhibit inhibitory effects on tumor growth and progression.
Used in Antioxidant Research:
(S)-4-HYDROXYMANDELONITRILE is also being investigated for its potential antioxidant properties, which could contribute to the prevention of oxidative stress and related diseases.
Used in Plant Defense Mechanisms:
(S)-4-Hydroxymandelonitrile plays a role in the defense mechanisms of plants against herbivores and pathogens, making it an important compound in the study of plant-pest interactions.
Used in Food Industry:
In the food industry, (S)-4-Hydroxymandelonitrile is of interest due to its contribution to the bitterness of almonds and other cyanogenic plants, which can impact the flavor and nutritional profile of these foods.

Upstream product

• 74-90-8 hydrogen cyanide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 

Relevant articles and documents

Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins

Hydroxynitrile lyase (HNL) catalyzed enantioselective C–C bond formation is an efficient approach to synthesize chiral cyanohydrins which are important building blocks in the synthesis of a number of fine chemicals, agrochemicals and pharmaceuticals. Immobilization of HNL is known to provide robustness, reusability and in some cases also enhances activity and selectivity. We optimized the preparation of immobilization of Baliospermium montanum HNL (BmHNL) by cross linking enzyme aggregate (CLEA) method and characterized it by SEM. Optimization of biocatalytic parameters was performed to obtain highest % conversion and ee of (S)-mandelonitrile from benzaldehyde using CLEA-BmHNL. The optimized reaction parameters were: 20 min of reaction time, 7 U of CLEA-BmHNL, 1.2 mM substrate, and 300 mM citrate buffer pH 4.2, that synthesized (S)-mandelonitrile in ～99% ee and ～60% conversion. Addition of organic solvent in CLEA-BmHNL biocatalysis did not improve in % ee or conversion of product unlike other CLEA-HNLs. CLEA-BmHNL could be successfully reused for eight consecutive cycles without loss of conversion or product formation and five cycles with a little loss in enantioselectivity. Eleven different chiral cyanohydrins were synthesized under optimal biocatalytic conditions in up to 99% ee and 59% conversion, however the % conversion and ee varied for different products. CLEA-BmHNL has improved the enantioselectivity of (S)-mandelonitrile synthesis compared to the use of purified BmHNL. Nine aldehydes not tested earlier with BmHNL were converted into their corresponding (S)-cyanohydrins for the first time using CLEA-BmHNL. Among the eleven (S)-cyanohydrins syntheses reported here, eight of them have not been synthesized by any CLEA-HNL. Overall, this study showed preparation, characterization of a stable, robust and recyclable biocatalyst i.e. CLEA-BmHNL and its biocatalytic application in the synthesis of different (S)-aromatic cyanohydrins.

Synthesis of aromatic 1,2-amino alcohols utilizing a bienzymatic dynamic kinetic asymmetric transformation

The applicability of the recent published bienzymatic protocol for the synthesis of (R)-2-amino-1-phenylethanol was tested using L-threonine aldolase from Pseudomonas putida and L-tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efil, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine and noradrenaline were obtained as (S)-enantiomers using Efil. Three protocols were upscaled yielding enantioenriched (S)-octopamine (yield 99%, ee 81%), (R)-2-amino-1-phenylethanol (yield 61%, ee 62%) and (S)-noradrenaline (yield 76%, ee 79%).

Novel (R)-oxynitrilase sources for the synthesis of (R)-cyanohydrins in diisopropyl ether

Apple, apricot, cherry and plum meal were prepared from the seeds or kernels of mature garden fruits. The preparations as well as almond meal were used as the source of (R)-oxynitrilase for the synthesis of aliphatic and aromatic cyanohydrins in diisoprop

(R)- and (S)-cyanohydrins using oxynitrilases in whole cells

Almond meal and Sorghum bicolor shoots were used as the sources of oxynitrilases for the preparation of a number (R)- and (S)-arylcyanohydrins, respectively, from the corresponding aldehydes in diisopropyl ether. Two different in situ methods were used to introduce hydrogen cyanide into the reaction mixture. In method 1, acetone cyanohydrin decomposes enzymatically and/or chemically to hydrogen cyanide. In method 2, hydrogen cyanide freely evaporates from a solution in diisopropyl ether from one compartment of the reaction vessel and ends up to the other where it dissolves into the reaction mixture.

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.