Mandelonitrile

Mandelonitrile
Mandelonitrile[1]
Identifiers
CAS number 532-28-5
PubChem 10758
ChemSpider 10304 YesY
KEGG C00561 YesY
ChEBI CHEBI:16910 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H7NO
Molar mass 133.15 g mol−1
Density 1.117 g/mL at 25 °C
Melting point

28-30 °C

Boiling point

170 °C

Hazards
R-phrases R23/24/25 R36/37/38 R41
S-phrases S22 S26 S36/37/39 S45
Main hazards toxic
Flash point 113 °C
Related compounds
Related compounds mandelic acid, phenylacetonitrile
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Mandelonitrile is a chemical compound of the cyanohydrin class. Small amounts of mandelonitrile occur in the pits of some fruits.

Occurrence

The naturally-occurring (R)-(+) enantiomer finds use as an intermediate in the preparation of optically active α-hydroxy carboxylic acids, α-hydroxy aldehydes, α-hydroxy ketones, and 2-amino alcohols[2].

Mandelonitrile is broken down into cyanide and benzaldehyde by the enzyme mandelonitrile lyase.

Preparation

Racemic 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:[3]

Preparation of mandelonitrile.png

References

  1. ^ Sigma-Aldrich product page
  2. ^ Kruse, C.G. In Collins, A.N. Sheldrake, G.N. Crosby, J., Eds. Chirality in Industry Chichester, UK , (1992), 279
  3. ^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941), "Mandelic Acid", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p0336 ; Coll. Vol. 1: 336 

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Look at other dictionaries:

  • mandelonitrile — noun A cyanohydrin found in the pits of some fruits, used as an intermediate in the preparation of certain chemical compounds …   Wiktionary

  • mandelonitrile — man·de·lo·ni·trile .man də lō nī trəl, .trīl n a yellow oily liquid C8H7NO that can be prepared by hydrolysis of amygdalin and yields a small amount of hydrogen cyanide when mixed with alcohol and water …   Medical dictionary

  • mandelonitrile — …   Useful english dictionary

  • Mandelonitrile lyase — Identifiers EC number 4.1.2.10 CAS number 9024 43 5 …   Wikipedia

  • Mandelonitrile-b-gentiobioside — Amygdaline Amygdaline Structure de l Amygdaline. Général Synonymes Amygdaloside Laetrile Mandelonitrile beta Gen …   Wikipédia en Français

  • Mandelic acid — Mandelic acid[1] IUPAC name 2 Hyd …   Wikipedia

  • Cyanohydrin — The structure of a general cyanohydrin. A cyanohydrin is a functional group found in organic compounds. Cyanohydrins have the formula R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids… …   Wikipedia

  • Amygdalin — Amygdalin …   Wikipedia

  • Prunasin beta-glucosidase — In enzymology, a prunasin beta glucosidase (EC number|3.2.1.118) is an enzyme that catalyzes the chemical reaction:(R) prunasin + H2O ightleftharpoons D glucose + mandelonitrileThus, the two substrates of this enzyme are (R) prunasin and H2O,… …   Wikipedia

  • Vicianin beta-glucosidase — In enzymology, a vicianin beta glucosidase (EC number|3.2.1.119) is an enzyme that catalyzes the chemical reaction:(R) vicianin + H2O ightleftharpoons mandelonitrile + vicianoseThus, the two substrates of this enzyme are (R) vicianin and H2O,… …   Wikipedia

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