cyanohydrin

A cyanohydrin is a functional group found in organic compounds.

Mandelonitrile is a chemical compound of the cyanohydrin class.

It is the simplest cyanohydrin, being derived from formaldehyde.

A functional group with a hydroxyl and cyanide bonded to the same carbon is called cyanohydrin.

The compound is generated as part of the acetone cyanohydrin route to methyl methacrylate.

The product is an O-silylated cyanohydrin.

Other now abandoned precursors to acrylic acid include ethenone and ethylene cyanohydrin.

It is a glucoside of acetone cyanohydrin.

Acetone cyanohydrin can be used to reversibly generate the cyanide anion.

It begins with the initial conversion of acetone to acetone cyanohydrin:

The addition of KCN to the carbonyl compound gives rise to the cyanohydrin.

Other names in common use include cyanohydrin glucosyltransferase, and uridine diphosphoglucose-cyanohydrin glucosyltransferase.

In one route, acetone cyanohydrin is converted to methacrylamide sulfate using sulfuric acid.

Crushing the tubers releases these compounds and produces acetone cyanohydrin, which is potentially lethally toxic.

In the laboratory, 2-aminoisobutyric acid may be prepared from acetone cyanohydrin, by reaction with ammonia followed by hydrolysis.

The principal hazards of acetone cyanohydrin arise from its ready decomposition on contact with water, which releases highly toxic hydrogen cyanide.

However, the toxicity is believed to be induced by ingestion of acetone cyanohydrin, the breakdown product of linamarin.

The cyanohydrins are a special class of nitriles that result from the addition of metal cyanides to aldehydes in the cyanohydrin reaction.

The original version of the Kiliani-Fischer synthesis proceeds through cyanohydrin and aldonic acid lactone intermediates.

The ketone was converted into cyanohydrin 29 with trimethylsilyl cyanide, potassium cyanide and a crown ether.

However, until 1960 a key production process was addition of hydrogen cyanide to ethylene oxide, followed by dehydration of the resulting cyanohydrin:

For alkali metal cyanide methods and methods employing acetone cyanohydrin, alcoholic solvents are commonly used.

Hence, this enzyme has one substrate, acetone cyanohydrin, and two products, cyanide and acetone.

Once the nucleophilic aldehyde is formed, whether as a cyanohydrin or stabilized by a thiazolium ylide, the reaction can proceed down two pathways.

Treatment of this cyanohydrin with lithium hydride affords anhydrous lithium cyanide: