Record Information |
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Version | 2.0 |
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Creation Date | 2012-08-09 09:16:12 -0600 |
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Update Date | 2015-09-13 12:56:16 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | Phenyllactic acid |
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Description | Phenyllactic acid is a lactic acid in which one of the methyl hydrogens is substituted by a phenyl group. Phenyllactic acid (or 3-phenyllactic acid) has two stereoisomers: (R)-3-phenyllactic acid and (S)-3-phenyllactic acid. (ChEBI) Phenyllactic acid is also similar in structure to the amino acid phenylalanine, except with the amino group in phenylalanine replaced by a hydroxyl group. (inferred from compound structure) |
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Structure | |
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Synonyms: | - 2-Hydroxy-3-phenylpropanoate
- 2-Hydroxy-3-phenylpropanoic acid
- 2-Hydroxy-3-phenylpropionate
- 2-Hydroxy-3-phenylpropionic acid
- 3-Phenyl-2-hydroxypropanoate
- 3-Phenyl-2-hydroxypropanoic acid
- 3-Phenyllactate
- 3-Phenyllactic acid
- A-Hydroxybenzenepropanoate
- A-Hydroxybenzenepropanoic acid
- Alpha-Hydroxybenzenepropanoate
- Alpha-Hydroxybenzenepropanoic acid
- B-Phenyllactate
- b-Phenyllactic acid
- Beta-Phenyllactate
- Beta-Phenyllactic acid
- DL-2-Hydroxy-3-phenylpropionate
- DL-2-Hydroxy-3-phenylpropionic acid
- DL-3-Phenyllactate
- DL-3-Phenyllactic acid
- DL-b-Phenyllactate
- DL-b-Phenyllactic acid
- DL-beta-Phenyllactate
- DL-beta-Phenyllactic acid
- DL-β-Phenyllactate
- DL-β-Phenyllactic acid
- Phenyllactate
- α-Hydroxybenzenepropanoate
- α-Hydroxybenzenepropanoic acid
- β-Phenyllactate
- β-Phenyllactic acid
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Chemical Formula: | C9H10O3 |
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Weight: | Average: 166.1739 Monoisotopic: 166.062994186 |
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InChI Key: | VOXXWSYKYCBWHO-UHFFFAOYSA-N |
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InChI: | InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12) |
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CAS number: | 828-01-3 |
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IUPAC Name: | 2-hydroxy-3-phenylpropanoic acid |
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Traditional IUPAC Name: | β-phenyllactic acid |
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SMILES: | OC(CC1=CC=CC=C1)C(O)=O |
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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
- Tertiary 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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Physical Properties |
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State: | Solid |
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Charge: | -1 |
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Melting point: | 98 °C |
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Experimental Properties: | Property | Value | Source |
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LogP: | 1.83 [HANSCH,C ET AL. (1995)] | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | Not Available |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0006-2930000000-9c44eea65a6e20c158ee | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0006-2930000000-9c44eea65a6e20c158ee | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0007-1910000000-1c581a4eacd9a7f2036f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9300000000-750e52d0df9e2b90be09 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-006x-9540000000-c06e2865c7cf1c780f11 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-014i-0900000000-cfbc3d9f0107a37ad7f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-00kb-1900000000-e1937415e710a88af8db | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0v4i-4900000000-f7887dfe1f265bcf46ba | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-0v00-6900000000-992cb5008b3e748b7e66 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-014i-0900000000-cfbc3d9f0107a37ad7f7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00kb-1900000000-a9ac61820c9f5278e2ba | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0v4i-4900000000-5e5e2d29a299435f9b35 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0v4i-6900000000-7df2fcf2f9b049e4c39f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0v00-6900000000-992cb5008b3e748b7e66 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-0002-0900000000-8940947cbb9a8e6253ee | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00si-9600000000-6ba02da72bb3acc762df | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0089-9700000000-901ab7fc4dce05d16406 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-017i-9100000000-248f4ab6119fb2bb911c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-1900000000-37469cb4526a3ed239e9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01bd-4900000000-f70272565fdcdbdf5209 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002f-9400000000-14afa00d4a96d888572b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-3900000000-15a50bcc903d54af3f43 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9400000000-0d7b49d15700ae266645 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9300000000-ca99933d289067e5347a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0900000000-a96f38f47d5e070f0989 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006t-1900000000-82f893f2df7cfa6f88eb | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f96-9400000000-50e3d4b82e667ef9e4d1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dl-5900000000-eb26ccce038261968168 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9300000000-aa44337c740dacf05e9c | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Iijima S, Ishii A, Miyakoshi T, Odaira T, Musha M: Studies on the experimental phenylketonuria in rats. Tohoku J Exp Med. 1975 Oct;117(2):167-78. Pubmed: 1209606
- Sarkissian CN, Scriver CR, Mamer OA: Measurement of phenyllactate, phenylacetate, and phenylpyruvate by negative ion chemical ionization-gas chromatography/mass spectrometry in brain of mouse genetic models of phenylketonuria and non-phenylketonuria hyperphenylalaninemia. Anal Biochem. 2000 May 1;280(2):242-9. Pubmed: 10790306
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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