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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:33:51 UTC
Update Date2023-02-21 17:24:20 UTC
HMDB IDHMDB0034666
Secondary Accession Numbers
  • HMDB34666
Metabolite Identification
Common Name(±)-2-Hydroxy-2-phenylacetonitrile
Description(±)-2-Hydroxy-2-phenylacetonitrile, also known as mandelonitrile, alpha-hydroxybenzeneacetonitrile or benzal dehyde cyanohydrin, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Mandelonitrile is a chemical compound of the cyanohydrin class. Hydroxy-2-phenylacetonitrile is a potentially toxic compound. The primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. (±)-2-Hydroxy-2-phenylacetonitrile has been detected, but not quantified, in fruits. This could make (±)-2-hydroxy-2-phenylacetonitrile a potential biomarker for the consumption of these foods. (±)-2- Oxygen therapy can also be administered.
Structure
Data?1677000260
Synonyms
ValueSource
alpha-HydroxybenzeneacetonitrileChEBI
Benzaldehyde cyanohydrinChEBI
Mandelic acid nitrileChEBI
PhenylglycolonitrileChEBI
a-HydroxybenzeneacetonitrileGenerator
Α-hydroxybenzeneacetonitrileGenerator
Mandelate nitrileGenerator
Mandelonitrile, (+-)-isomerHMDB
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name2-hydroxy-2-phenylacetonitrile
Traditional Namemandelonitrile
CAS Registry Number613-88-7
SMILES
OC(C#N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
InChI KeyNNICRUQPODTGRU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Alpha-hydroxynitrile
  • Secondary alcohol
  • Cyanohydrin
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point21.5 - 22 °CNot Available
Boiling Point282.70 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility46290 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.830 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.89 g/LALOGPS
logP0.68ALOGPS
logP0.95ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.8ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.68 m³·mol⁻¹ChemAxon
Polarizability13.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+127.66331661259
DarkChem[M-H]-123.88931661259
DeepCCS[M+H]+126.06430932474
DeepCCS[M-H]-122.75630932474
DeepCCS[M-2H]-159.79830932474
DeepCCS[M+Na]+135.07630932474
AllCCS[M+H]+128.232859911
AllCCS[M+H-H2O]+123.532859911
AllCCS[M+NH4]+132.632859911
AllCCS[M+Na]+133.932859911
AllCCS[M-H]-125.432859911
AllCCS[M+Na-2H]-127.032859911
AllCCS[M+HCOO]-128.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(??)-2-Hydroxy-2-phenylacetonitrileOC(C#N)C1=CC=CC=C12232.9Standard polar33892256
(??)-2-Hydroxy-2-phenylacetonitrileOC(C#N)C1=CC=CC=C11275.2Standard non polar33892256
(??)-2-Hydroxy-2-phenylacetonitrileOC(C#N)C1=CC=CC=C11325.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(??)-2-Hydroxy-2-phenylacetonitrile,1TMS,isomer #1C[Si](C)(C)OC(C#N)C1=CC=CC=C11370.0Semi standard non polar33892256
(??)-2-Hydroxy-2-phenylacetonitrile,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C#N)C1=CC=CC=C11557.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-EI-TOF (Non-derivatized)splash10-0a4l-2900000000-9bf5d9f7a830e077231e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-EI-TOF (Non-derivatized)splash10-0a4l-2900000000-9bf5d9f7a830e077231e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-7900000000-f3c0c0e7a3df24b1f83b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (1 TMS) - 70eV, Positivesplash10-0100-7900000000-11427484bfb13fd6a7a92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-9700000000-52314e45f42d178d3a852014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Positive-QTOFsplash10-001i-0900000000-7c24126e874e537eb2492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Positive-QTOFsplash10-05o0-0900000000-c346fce57e98f78257e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Positive-QTOFsplash10-0lfr-9700000000-228fb6b241946a8568d42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Negative-QTOFsplash10-001i-0900000000-ea6e429426ef964cc0812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Negative-QTOFsplash10-003r-4900000000-54d9f51720b51ca4117b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Negative-QTOFsplash10-004i-9200000000-4984b4790f404f8ab9c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Negative-QTOFsplash10-001i-4900000000-6f591a5616423a7c26c52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Negative-QTOFsplash10-0059-9600000000-f4b4bc42937e4ce43fd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Negative-QTOFsplash10-0kdi-6900000000-95f96f3606696317faf92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Positive-QTOFsplash10-014i-0900000000-ff2f50a1cd0316c3889d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Positive-QTOFsplash10-014i-2900000000-e7674fcadf80c742e74d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Positive-QTOFsplash10-02t9-9200000000-ee74ae1e15bd8bae88522021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013191
KNApSAcK IDC00051456
Chemspider ID10304
KEGG Compound IDNot Available
BioCyc IDMANDELONITRILE
BiGG IDNot Available
Wikipedia LinkMandelonitrile
METLIN IDNot Available
PubChem Compound10758
PDB IDNot Available
ChEBI ID16910
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1256421
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .