Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 19:33:51 UTC |
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Update Date | 2023-02-21 17:24:20 UTC |
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HMDB ID | HMDB0034666 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (±)-2-Hydroxy-2-phenylacetonitrile |
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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. |
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Structure | InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H |
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Synonyms | Value | Source |
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alpha-Hydroxybenzeneacetonitrile | ChEBI | Benzaldehyde cyanohydrin | ChEBI | Mandelic acid nitrile | ChEBI | Phenylglycolonitrile | ChEBI | a-Hydroxybenzeneacetonitrile | Generator | Α-hydroxybenzeneacetonitrile | Generator | Mandelate nitrile | Generator | Mandelonitrile, (+-)-isomer | HMDB |
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Chemical Formula | C8H7NO |
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Average Molecular Weight | 133.1473 |
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Monoisotopic Molecular Weight | 133.052763851 |
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IUPAC Name | 2-hydroxy-2-phenylacetonitrile |
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Traditional Name | mandelonitrile |
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CAS Registry Number | 613-88-7 |
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SMILES | OC(C#N)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H |
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InChI Key | NNICRUQPODTGRU-UHFFFAOYSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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 |
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