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Identification |
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YMDB ID | YMDB00457 |
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Name | 3-(4-hydroxyphenyl)lactic acid |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Hydroxyphenyllactic acid, also known as 4-hydroxyphenyllactate or HPLA, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Hydroxyphenyllactic acid exists in all eukaryotes, ranging from yeast to plants to humans. Based on a literature review a significant number of articles have been published on Hydroxyphenyllactic acid. |
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Structure | |
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Synonyms | - (RS)-3-(4-Hydroxyphenyl)lactate
- (RS)-3-(4-Hydroxyphenyl)lactic acid
- 2-Hydroxy-3-(4-hydroxyphenyl)propanoate
- 2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid
- 2-Hydroxy-3-(p-hydroxyphenyl)propionate
- 2-Hydroxy-3-(p-hydroxyphenyl)propionic acid
- 3-(4-Hydroxyphenyl)-DL-lactate
- 3-(4-Hydroxyphenyl)-DL-lactic acid
- 3-(4-Hydroxyphenyl)lactate
- 3-(4-Hydroxyphenyl)lactic acid
- 3-(p-hydroxyphenyl)-Lactate
- 3-(p-hydroxyphenyl)-Lactic acid
- 4-Hydroxyphenyllactate
- 4-Hydroxyphenyllactic acid
- a,4-Dihydroxybenzenepropanoate
- a,4-Dihydroxybenzenepropanoic acid
- b-(4-Hydroxyphenyl)lactate
- b-(4-Hydroxyphenyl)lactic acid
- b-(p-Hydroxyphenyl)-DL-lactate
- b-(p-Hydroxyphenyl)-DL-lactic acid
- b-(p-Hydroxyphenyl)lactate
- b-(p-Hydroxyphenyl)lactic acid
- Benzenepropanoic acid, .alpha.,4-dihydroxy-
- beta-(4-Hydroxyphenyl)lactate
- beta-(4-Hydroxyphenyl)lactic acid
- beta-(p-Hydroxyphenyl)-DL-lactate
- beta-(p-Hydroxyphenyl)-DL-lactic acid
- beta-(p-Hydroxyphenyl)lactate
- beta-(p-Hydroxyphenyl)lactic acid
- DL-3-(4-Hydroxyphenyl)lactate
- DL-3-(4-Hydroxyphenyl)lactic acid
- DL-p-Hydroxyphenyllactate
- DL-p-Hydroxyphenyllactic acid
- HPLA
- Hydroxyphenyllactate
- Lactic acid, (p-hydroxyphenyl)-
- Lactic acid, 3-(p-hydroxyphenyl)-
- p-Hydroxyphenyl lactic acid
- p-Hydroxyphenyllactate
- Β-(4-hydroxyphenyl)lactate
- Β-(4-hydroxyphenyl)lactic acid
- Β-(p-hydroxyphenyl)lactate
- Β-(p-hydroxyphenyl)lactic acid
- p-Hydroxyphenyl lactate
- p-Hydroxyphenyllactic acid
- 4-Hydroxyphenyllactic acid, (DL)-isomer
- Para-hydroxyphenyllactic acid
- 2-Hydroxyphloretate
- 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid
- 2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid
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CAS number | 306-23-0 |
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Weight | Average: 182.1733 Monoisotopic: 182.057908808 |
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InChI Key | JVGVDSSUAVXRDY-UHFFFAOYSA-N |
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InChI | InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13) |
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IUPAC Name | 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid |
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Traditional IUPAC Name | hydroxyphenyllactic acid |
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Chemical Formula | C9H10O4 |
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SMILES | OC(CC1=CC=C(O)C=C1)C(O)=O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Phenylpropanoic acids |
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Sub Class | Not Available |
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Direct Parent | Phenylpropanoic acids |
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Alternative Parents | |
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Substituents | - 3-phenylpropanoic-acid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Alpha-hydroxy acid
- Monocyclic benzene moiety
- Benzenoid
- Hydroxy acid
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Alcohol
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- 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 | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | 12.9 mg/mL at 16 oC [BEILSTEIN] | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Tyrosine metabolism | ec00350 |  | Ubiquinone and other terpenoid-quinone biosynthesis | ec00130 |  |
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SMPDB Reactions | Not Available |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (3 TMS) | splash10-004i-1911000000-424dc0a114976e4a6052 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-004i-1911000000-424dc0a114976e4a6052 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-004i-0900000000-b7f0ddb24f5c187d4540 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4r-3900000000-aece5a68ba54ab74c5ee | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-003r-5496000000-fbb65d0c963e70625e95 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00li-2900000000-ea59f9dcf58b55bec6ca | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-054n-9300000000-5b39aa5183630ccd7f4d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0k92-9200000000-c698fdbe1eefac6e9eab | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-01qi-0900000000-640a5a477752571a1443 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-03di-0900000000-45b5f23bae1a9641fb0b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-01qi-0900000000-640a5a477752571a1443 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - , negative | splash10-03ei-0900000000-d89828d3625adabd215b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-00ou-9000000000-60dd6237cac5c79c7508 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00ri-2900000000-69365cb4d9937f6a96e0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00li-1900000000-03a7d2e8f219eba66eee | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-029i-0900000000-fd70bef080a1a354df5a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9400000000-65da3c598368dbad66cd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-052b-9100000000-6ad54b488ac0183ff4bf | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0002-9400000000-af41107b1e7be38f765c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-023a994f4d18e32123cd | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-001i-5900000000-8fcf87adaaae828f3aae | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00ri-2900000000-ed974245d122fcbc31c0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03ei-1900000000-fd1d5ff4f32cdcdf0a38 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00ec-9400000000-9b26dc9e6bb4e1a72cfb | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05o9-0900000000-a343595d5c411e940c25 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ap0-0900000000-1f777ab6b9486c181355 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-9800000000-db82c9bf8afdb32af6de | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-2900000000-3e1a7023e9214816e8a5 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-052r-2900000000-c05e995d8c57a180bae7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mx-9800000000-729b43ad9499a14c2d01 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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References: | - Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
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Synthesis Reference: | Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13. |
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External Links: | |
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