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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:33:51 UTC

Update Date

2023-02-21 17:24:20 UTC

HMDB ID

HMDB0034666

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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Hydroxybenzeneacetonitrile	ChEBI
Benzaldehyde cyanohydrin	ChEBI
Mandelic acid nitrile	ChEBI
Phenylglycolonitrile	ChEBI
a-Hydroxybenzeneacetonitrile	Generator
Α-hydroxybenzeneacetonitrile	Generator
Mandelate nitrile	Generator
Mandelonitrile, (+-)-isomer	HMDB

Chemical Formula

C₈H₇NO

Average Molecular Weight

133.1473

Monoisotopic Molecular Weight

133.052763851

IUPAC Name

2-hydroxy-2-phenylacetonitrile

Traditional Name

mandelonitrile

CAS Registry Number

613-88-7

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 Key

NNICRUQPODTGRU-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

cyanohydrin (CHEBI:16910 )
mandelonitrile (CPD-12702 )

Ontology

Not Available

Exogenous (HMDB: HMDB34666)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	21.5 - 22 °C	Not Available
Boiling Point	282.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	46290 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.830 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.89 g/L	ALOGPS
logP	0.68	ALOGPS
logP	0.95	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.8	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	44.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.68 m³·mol⁻¹	ChemAxon
Polarizability	13.55 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	127.663	31661259
DarkChem	[M-H]-	123.889	31661259
DeepCCS	[M+H]+	126.064	30932474
DeepCCS	[M-H]-	122.756	30932474
DeepCCS	[M-2H]-	159.798	30932474
DeepCCS	[M+Na]+	135.076	30932474
AllCCS	[M+H]+	128.2	32859911
AllCCS	[M+H-H2O]+	123.5	32859911
AllCCS	[M+NH4]+	132.6	32859911
AllCCS	[M+Na]+	133.9	32859911
AllCCS	[M-H]-	125.4	32859911
AllCCS	[M+Na-2H]-	127.0	32859911
AllCCS	[M+HCOO]-	128.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-2-Hydroxy-2-phenylacetonitrile	OC(C#N)C1=CC=CC=C1	2232.9	Standard polar	33892256
(??)-2-Hydroxy-2-phenylacetonitrile	OC(C#N)C1=CC=CC=C1	1275.2	Standard non polar	33892256
(??)-2-Hydroxy-2-phenylacetonitrile	OC(C#N)C1=CC=CC=C1	1325.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(??)-2-Hydroxy-2-phenylacetonitrile,1TMS,isomer #1	C[Si](C)(C)OC(C#N)C1=CC=CC=C1	1370.0	Semi standard non polar	33892256
(??)-2-Hydroxy-2-phenylacetonitrile,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(C#N)C1=CC=CC=C1	1557.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-EI-TOF (Non-derivatized)	splash10-0a4l-2900000000-9bf5d9f7a830e077231e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-EI-TOF (Non-derivatized)	splash10-0a4l-2900000000-9bf5d9f7a830e077231e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-7900000000-f3c0c0e7a3df24b1f83b	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (1 TMS) - 70eV, Positive	splash10-0100-7900000000-11427484bfb13fd6a7a9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a6r-9700000000-52314e45f42d178d3a85	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Positive-QTOF	splash10-001i-0900000000-7c24126e874e537eb249	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Positive-QTOF	splash10-05o0-0900000000-c346fce57e98f78257e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Positive-QTOF	splash10-0lfr-9700000000-228fb6b241946a8568d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Negative-QTOF	splash10-001i-0900000000-ea6e429426ef964cc081	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Negative-QTOF	splash10-003r-4900000000-54d9f51720b51ca4117b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Negative-QTOF	splash10-004i-9200000000-4984b4790f404f8ab9c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Negative-QTOF	splash10-001i-4900000000-6f591a5616423a7c26c5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Negative-QTOF	splash10-0059-9600000000-f4b4bc42937e4ce43fd6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Negative-QTOF	splash10-0kdi-6900000000-95f96f3606696317faf9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 10V, Positive-QTOF	splash10-014i-0900000000-ff2f50a1cd0316c3889d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 20V, Positive-QTOF	splash10-014i-2900000000-e7674fcadf80c742e74d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-2-Hydroxy-2-phenylacetonitrile 40V, Positive-QTOF	splash10-02t9-9200000000-ee74ae1e15bd8bae8852	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013191

KNApSAcK ID

C00051456

Chemspider ID

10304

KEGG Compound ID

Not Available

BioCyc ID

MANDELONITRILE

BiGG ID

Not Available

Wikipedia Link

Mandelonitrile

METLIN ID

Not Available

PubChem Compound

10758

PDB ID

Not Available

ChEBI ID

16910

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1256421

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-2-Hydroxy-2-phenylacetonitrile (HMDB0034666)

MOL for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

3D MOL for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

3D SDF for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

3D-SDF for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

PDB for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

3D PDB for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

SMILES for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

INCHI for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

Structure for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

3D Structure for HMDB0034666 ((±)-2-Hydroxy-2-phenylacetonitrile)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra