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Mandelonitrile information


Mandelonitrile[1]
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-Hydroxy-2-phenylacetonitrile
Other names
α-Hydroxybenzeneacetonitrile
Identifiers
CAS Number
  • 532-28-5 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
2207122
ChEBI
  • CHEBI:16910 checkY
ChEMBL
  • ChEMBL1393845
ChemSpider
  • 10304 checkY
ECHA InfoCard 100.007.758 Edit this at Wikidata
EC Number
  • 208-532-7
Gmelin Reference
1684586
KEGG
  • C00561 checkY
PubChem CID
  • 10758
UNII
  • 584322E08A checkY
UN number 2810
CompTox Dashboard (EPA)
  • DTXSID2025422 Edit this at Wikidata
InChI
  • InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H checkY
    Key: NNICRUQPODTGRU-UHFFFAOYSA-N checkY
  • InChI=1/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
    Key: NNICRUQPODTGRU-UHFFFAOYAG
SMILES
  • N#CC(O)c1ccccc1
Properties
Chemical formula
C8H7NO
Molar mass 133.150 g·mol−1
Density 1.117 g/mL
Melting point 22 °C (72 °F; 295 K) (R/S)[2]
Boiling point 282.70 °C (540.86 °F; 555.85 K) Decomposes[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
toxic
Flash point 113 °C (235 °F; 386 K)
Related compounds
Related compounds
mandelic acid, phenylacetonitrile
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In organic chemistry, mandelonitrile is the nitrile of mandelic acid, or the cyanohydrin derivative of benzaldehyde. Small amounts of mandelonitrile occur in the pits of some fruits.

  1. ^ Sigma-Aldrich product page
  2. ^ a b The Merck Index (12th ed.). 1996.

and 18 Related for: Mandelonitrile information

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Mandelonitrile

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chemistry, mandelonitrile is the nitrile of mandelic acid, or the cyanohydrin derivative of benzaldehyde. Small amounts of mandelonitrile occur in the...

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Prunasin

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glycoside related to amygdalin. Chemically, it is the glucoside of (R)-mandelonitrile. Prunasin is found in species in the genus Prunus such as Prunus japonica...

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Mandelonitrile lyase

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enzyme (R)-mandelonitrile lyase (EC 4.1.2.10, (R)-HNL, (R)-oxynitrilase, (R)-hydroxynitrile lyase) catalyzes the chemical reaction mandelonitrile ⇌ {\displaystyle...

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Amygdalin

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(amygdalase) to give gentiobiose and L-mandelonitrile. Gentiobiose is further hydrolyzed to give glucose, whereas mandelonitrile (the cyanohydrin of benzaldehyde)...

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Mandelic acid

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prepared by the acid-catalysed hydrolysis of mandelonitrile, which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde...

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Cyanohydrin

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relying on ester, phosphate and carbonate formation have been reported. Mandelonitrile, with the formula C6H5CH(OH)CN, occurs in small amounts in the pits...

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Prunus serotina

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enzymes include amygdalin beta-glucosidase, prunasin beta-glucosidase and mandelonitrile lyase. In contrast, although the flesh of black cherries also contains...

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Microbacterium paraoxydans

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can cause disease in fish. Microbacterium paraoxydans metabolize (RS)-mandelonitrile to (R)-(-)mandelic acid. Microbacterium paraoxydans is a plant growth-promoting...

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Hydrogen cyanide

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made. Many of these pits contain small amounts of cyanohydrins such as mandelonitrile and amygdalin, which slowly release hydrogen cyanide. One hundred grams...

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Centipede

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Jerrold; Eisner, Hans E.; Eisner, Thomas (1976). "Benzoyl cyanide and mandelonitrile in the cyanogenetic secretion of a centipede". Journal of Chemical Ecology...

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Nitrile

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sprouts, and cauliflower), which release nitriles through hydrolysis. Mandelonitrile, a cyanohydrin produced by ingesting almonds or some fruit pits, releases...

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Diamondback soil centipede

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secretion is proteinaceous and contains two cyanogenetic compounds, mandelonitrile and benzoyl cyanide, as well as two products derived from these compounds...

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Vicianin

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enzyme vicianin beta-glucosidase uses (R)-vicianin and H2O to produce mandelonitrile and vicianose. It is found in seeds of Vicia angustifolia. Ahn, Y. O...

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C8H7NO

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mass: 133.14728 g/mol, exact mass: 133.052764 u) may refer to: Indoxyl Mandelonitrile Oxindole (2-indolone) This set index page lists chemical structure articles...

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Vicianose

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enzyme vicianin beta-glucosidase uses (R)-vicianin and water to produce mandelonitrile and vicianose. The fruits of Viburnum dentatum appear blue. One of the...

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Mandelamide amidase

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Fujimatsu I, Komatsu K (1991). "Production of R-(−)-mandelic acid from mandelonitrile by Alcaligenes faecalis ATCC 8750". Appl. Environ. Microbiol. 57 (10):...

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Nitrilase

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source. P. fluorescens EBC191 hydrolyzes many arylacetonitriles, namely mandelonitrile, which serves as a defense against herbivores. Winkler M, Glieder A...

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Mare reproductive loss syndrome

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thought to be the causative agent. Administration of both cyanide and mandelonitrile (a cyanide-containing chemical in cherry leaves) to horses demonstrated...

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