Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2017-03-23 04:56:21 UTC |
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Update Date | 2022-03-07 03:17:57 UTC |
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HMDB ID | HMDB0062635 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (R)-mandelic Acid |
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Description | (R)-mandelic Acid, also known as (R)-mandelsaeure or D-2-phenylglycolate, 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 (R)-mandelic Acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (R)-mandelic Acid exists in all living organisms, ranging from bacteria to humans. The (R)-enantiomer of mandelic acid. |
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Structure | O[C@@H](C(O)=O)C1=CC=CC=C1 InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1 |
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Synonyms | Value | Source |
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(-)-(R)-Mandelic acid | ChEBI | (-)-alpha-Hydroxyphenylacetic acid | ChEBI | (-)-Mandelic acid | ChEBI | (2R)-2-Hydroxy-2-phenylacetic acid | ChEBI | (R)-2-Hydroxy-2-phenylacetic acid | ChEBI | (R)-alpha-Hydroxybenzeneacetic acid | ChEBI | (R)-alpha-Hydroxyphenylacetic acid | ChEBI | (R)-Mandelsaeure | ChEBI | D(-)-Mandelic acid | ChEBI | D-2-Phenylglycolic acid | ChEBI | D-Mandelic acid | ChEBI | (R)-2-Hydroxy-2-phenylacetate | Kegg | (-)-(R)-Mandelate | Generator | (-)-a-Hydroxyphenylacetate | Generator | (-)-a-Hydroxyphenylacetic acid | Generator | (-)-alpha-Hydroxyphenylacetate | Generator | (-)-Α-hydroxyphenylacetate | Generator | (-)-Α-hydroxyphenylacetic acid | Generator | (-)-Mandelate | Generator | (2R)-2-Hydroxy-2-phenylacetate | Generator | (R)-a-Hydroxybenzeneacetate | Generator | (R)-a-Hydroxybenzeneacetic acid | Generator | (R)-alpha-Hydroxybenzeneacetate | Generator | (R)-Α-hydroxybenzeneacetate | Generator | (R)-Α-hydroxybenzeneacetic acid | Generator | (R)-a-Hydroxyphenylacetate | Generator | (R)-a-Hydroxyphenylacetic acid | Generator | (R)-alpha-Hydroxyphenylacetate | Generator | (R)-Α-hydroxyphenylacetate | Generator | (R)-Α-hydroxyphenylacetic acid | Generator | D(-)-Mandelate | Generator | D-2-Phenylglycolate | Generator | D-Mandelate | Generator | (R)-Mandelate | Generator |
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Chemical Formula | C8H8O3 |
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Average Molecular Weight | 152.1473 |
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Monoisotopic Molecular Weight | 152.047344122 |
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IUPAC Name | (2R)-2-hydroxy-2-phenylacetic acid |
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Traditional Name | mandelic acid, (+-)- |
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CAS Registry Number | 611-71-2 |
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SMILES | O[C@@H](C(O)=O)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1 |
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InChI Key | IWYDHOAUDWTVEP-SSDOTTSWSA-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 | - Hydroxy acid
- Monocyclic benzene moiety
- Alpha-hydroxy acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Aromatic alcohol
- Organooxygen compound
- Carbonyl group
- 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 | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 16.8 g/l | ALOGPS | LogP | 0.66 | ALOGPS |
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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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(R)-mandelic Acid,1TMS,isomer #1 | C[Si](C)(C)O[C@@H](C(=O)O)C1=CC=CC=C1 | 1460.9 | Semi standard non polar | 33892256 | (R)-mandelic Acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](O)C1=CC=CC=C1 | 1414.7 | Semi standard non polar | 33892256 | (R)-mandelic Acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)C1=CC=CC=C1 | 1474.7 | Semi standard non polar | 33892256 | (R)-mandelic Acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)C1=CC=CC=C1 | 1697.0 | Semi standard non polar | 33892256 | (R)-mandelic Acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)C1=CC=CC=C1 | 1652.5 | Semi standard non polar | 33892256 | (R)-mandelic Acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1 | 1927.8 | Semi standard non polar | 33892256 |
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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 - (R)-mandelic Acid EI-B (Non-derivatized) | splash10-004i-0900000000-da7c8450b1708d6b5b44 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (R)-mandelic Acid GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-bf406a068b57bcc07ca2 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (R)-mandelic Acid EI-B (Non-derivatized) | splash10-004i-0900000000-da7c8450b1708d6b5b44 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - (R)-mandelic Acid GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-bf406a068b57bcc07ca2 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-9600000000-0d67f110027658a584a4 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (2 TMS) - 70eV, Positive | splash10-004i-2910000000-de71bbd7bcfd35e2bbe5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-mandelic Acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOF | splash10-0zfr-5900000000-45499f2c996208e0143f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9100000000-b577195913c64f43bc8f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-3030385b2c46c76f7d40 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-d57db09a0e7c73a976bc | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-5a80a2a733ffb7d2962f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - (R)-mandelic Acid LC-ESI-QTOF , negative-QTOF | splash10-0udi-0900000000-26a5fcf7f098faa99c2d | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Positive-QTOF | splash10-0zg0-0900000000-dc883eccc7ede3626274 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Positive-QTOF | splash10-0a4i-1900000000-43028c230f4ad5a4568c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Positive-QTOF | splash10-0pdi-9500000000-d3b486d397a2e852f3a4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Negative-QTOF | splash10-0zfr-0900000000-d3c9a003466ac58be74f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Negative-QTOF | splash10-0pdi-5900000000-cadf8b3761e31a6e33c5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Negative-QTOF | splash10-004i-9200000000-b906b74a2aa4ffe7facc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Positive-QTOF | splash10-00kr-1900000000-1f844c7b2df8e11ad51c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Positive-QTOF | splash10-004i-9100000000-8dc4c2ee7a401fec29d6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Positive-QTOF | splash10-004i-9000000000-a072eb0e14ea716c51b0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 10V, Negative-QTOF | splash10-0zfr-1900000000-62ebdc9508b56ca81f8a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 20V, Negative-QTOF | splash10-0a6r-7900000000-1f515b6e62c594acde14 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-mandelic Acid 40V, Negative-QTOF | splash10-01t9-9000000000-08231d859a98c3eafb22 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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 | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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