Mandelonitrile
Encyclopedia
Mandelonitrile is a chemical compound
of the cyanohydrin
class. Small amounts of mandelonitrile occur in the pits
of some fruits.
, α-hydroxy aldehydes, α-hydroxy ketones, and 2-amino alcohols
.
Mandelonitrile is broken down into cyanide
and benzaldehyde
by the enzyme mandelonitrile lyase
.
mandelonitrile may be prepared similar to many other cyanohydrins. In a one pot reaction, benzaldehyde
is reacted with sodium bisulfite
to give the corresponding adduct, which further reacts with aqueous sodium cyanide
to give the racemic product:
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
of the cyanohydrin
Cyanohydrin
A cyanohydrin is a functional group found in organic compounds. Cyanohydrins have the formula R2CCN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids...
class. Small amounts of mandelonitrile occur in the pits
Drupe
In botany, a drupe is a fruit in which an outer fleshy part surrounds a shell of hardened endocarp with a seed inside. These fruits develop from a single carpel, and mostly from flowers with superior ovaries...
of some fruits.
Occurrence
The naturally-occurring (R)-(+) enantiomer finds use as an intermediate in the preparation of optically active α-hydroxy carboxylic acidsAlpha hydroxy acid
α-Hydroxy acids, or alpha hydroxy acids , are a class of chemical compounds that consist of a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. They may be either naturally occurring or synthetic. AHAs are well-known for their use in the cosmetics industry...
, α-hydroxy aldehydes, α-hydroxy ketones, and 2-amino alcohols
Amino alcohol
Amino alcohols are organic compounds that contain both an amine functional group and an alcohol functional group.-Common amino alcohols:* Ethanolamines* Heptaminol* Isoetarine* Norepinephrine* Propanolamines* Sphingosine...
.
Mandelonitrile is broken down into cyanide
Cyanide
A cyanide is a chemical compound that contains the cyano group, -C≡N, which consists of a carbon atom triple-bonded to a nitrogen atom. Cyanides most commonly refer to salts of the anion CN−. Most cyanides are highly toxic....
and benzaldehyde
Benzaldehyde
Benzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. This colorless liquid has a characteristic pleasant almond-like odor...
by the enzyme mandelonitrile lyase
Mandelonitrile lyase
In enzymology, a mandelonitrile lyase is an enzyme that catalyzes the chemical reactionHence, this enzyme has one substrate, mandelonitrile, and two products, cyanide and benzaldehyde....
.
Preparation
RacemicRacemic
In chemistry, a racemic mixture, or racemate , is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule. The first known racemic mixture was "racemic acid", which Louis Pasteur found to be a mixture of the two enantiomeric isomers of tartaric acid.- Nomenclature :A...
mandelonitrile may be prepared similar to many other cyanohydrins. In a one pot reaction, benzaldehyde
Benzaldehyde
Benzaldehyde is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful. This colorless liquid has a characteristic pleasant almond-like odor...
is reacted with sodium bisulfite
Sodium bisulfite
Sodium bisulfite is a chemical compound with the chemical formula NaHSO3. Sodium bisulfite is a food additive with E number E222. This salt of bisulfite can be prepared by bubbling sulfur dioxide in a solution of sodium carbonate in water...
to give the corresponding adduct, which further reacts with aqueous sodium cyanide
Sodium cyanide
Sodium cyanide is an inorganic compound with the formula NaCN. This highly toxic colorless salt is used mainly in gold mining but has other niche applications...
to give the racemic product:
