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| Record Information |
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| Version | 3.6 |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2017-03-02 21:26:09 UTC |
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| HMDB ID | HMDB00755 |
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| Secondary Accession Numbers | None |
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| Metabolite Identification |
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| Common Name | Hydroxyphenyllactic acid |
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| Description | Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2). (PMID 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia. (PMID: 3126358 ). However the D-form of hydroxyphneyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produced considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2-Hydroxy-3-(4-hydroxyphenyl)propanoate | ChEBI | | 2-Hydroxy-3-(P-hydroxyphenyl)propionic acid | ChEBI | | 4-Hydroxyphenyllactic acid | ChEBI | | beta-(4-Hydroxyphenyl)lactic acid | ChEBI | | beta-(P-Hydroxyphenyl)lactic acid | ChEBI | | DL-P-Hydroxyphenyllactic acid | ChEBI | | P-Hydroxyphenyl lactic acid | ChEBI | | 2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid | Generator | | Hydroxyphenyllactate | Generator | | 2-Hydroxy-3-(P-hydroxyphenyl)propionate | Generator | | 4-Hydroxyphenyllactate | Generator | | b-(4-Hydroxyphenyl)lactate | Generator | | b-(4-Hydroxyphenyl)lactic acid | Generator | | beta-(4-Hydroxyphenyl)lactate | Generator | | β-(4-hydroxyphenyl)lactate | Generator | | β-(4-hydroxyphenyl)lactic acid | Generator | | b-(P-Hydroxyphenyl)lactate | Generator | | b-(P-Hydroxyphenyl)lactic acid | Generator | | beta-(P-Hydroxyphenyl)lactate | Generator | | β-(P-hydroxyphenyl)lactate | Generator | | β-(P-hydroxyphenyl)lactic acid | Generator | | DL-P-Hydroxyphenyllactate | Generator | | P-Hydroxyphenyl lactate | Generator | | (RS)-3-(4-Hydroxyphenyl)lactate | HMDB | | (RS)-3-(4-Hydroxyphenyl)lactic acid | HMDB | | 3-(4-Hydroxyphenyl)-DL-lactate | HMDB | | 3-(4-Hydroxyphenyl)-DL-lactic acid | HMDB | | 3-(4-Hydroxyphenyl)lactate | HMDB | | 3-(4-Hydroxyphenyl)lactic acid | HMDB | | 3-(P-Hydroxyphenyl)-lactate | HMDB | | 3-(P-Hydroxyphenyl)-lactic acid | HMDB | | a,4-Dihydroxybenzenepropanoate | HMDB | | a,4-Dihydroxybenzenepropanoic acid | HMDB | | b-(P-Hydroxyphenyl)-DL-lactate | HMDB | | b-(P-Hydroxyphenyl)-DL-lactic acid | HMDB | | beta-(P-Hydroxyphenyl)-DL-lactate | HMDB | | beta-(P-Hydroxyphenyl)-DL-lactic acid | HMDB | | DL-3-(4-Hydroxyphenyl)lactate | HMDB | | DL-3-(4-Hydroxyphenyl)lactic acid | HMDB | | HPLA | HMDB | | 4-Hydroxyphenyllactic acid, (DL)-isomer | MeSH | | Para-hydroxyphenyllactic acid | MeSH | | P-Hydroxyphenyllactate | MeSH |
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| Chemical Formula | C9H10O4 |
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| Average Molecular Weight | 182.1733 |
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| Monoisotopic Molecular Weight | 182.057908808 |
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| IUPAC Name | 2-hydroxy-3-(4-hydroxyphenyl)propanoic acid |
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| Traditional Name | hydroxyphenyllactic acid |
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| CAS Registry Number | 306-23-0 |
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| SMILES | OC(CC1=CC=C(O)C=C1)C(O)=O |
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| InChI Identifier | 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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| InChI Key | JVGVDSSUAVXRDY-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | This compound belongs to the class of chemical entities known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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| Kingdom | Chemical entities |
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| Super Class | Organic compounds |
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| Class | Phenylpropanoids and polyketides |
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| Sub Class | Phenylpropanoic acids |
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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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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 12.9 mg/mL at 16 °C | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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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 (3 TMS) | splash10-004i-1911000000-424dc0a114976e4a6052 | View in MoNA |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | Not Available |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF | splash10-004i-0900000000-b7f0ddb24f5c187d4540 | View in MoNA |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF | splash10-004i-0900000000-b7f0ddb24f5c187d4540 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00li-2900000000-ea59f9dcf58b55bec6ca | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-054n-9300000000-5b39aa5183630ccd7f4d | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0k92-9200000000-c698fdbe1eefac6e9eab | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-01qi-0900000000-640a5a477752571a1443 | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , negative | splash10-03di-0900000000-45b5f23bae1a9641fb0b | View in MoNA |
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| LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-TOF , negative | splash10-03ei-0900000000-d89828d3625adabd215b | View in MoNA |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available |
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| 1D NMR | 1H NMR Spectrum | Not Available |
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| 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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| Biological Properties |
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| Cellular Locations | |
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| Biofluid Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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| Tissue Location | |
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| Pathways | Not Available |
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| Normal Concentrations |
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| Blood | Detected and Quantified | 0.64 +/- 0.24 uM | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Applicable | Children (1-13 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | Not Applicable | Infant (0-1 year old) | Not Available | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected and Quantified | 25.10 +/- 14.93 uM | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.55-1.2 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | | Urine | Detected and Quantified | 5.393 +/- 4.849 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected and Quantified | 35.939 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 1.05 +/- 0.43 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 1.1 (0.2-2.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 3.7 (0.1-11.5) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | | Urine | Detected and Quantified | 4.8 (2.7-5.3) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | | Urine | Detected and Quantified | 0.51-0.94 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | | Urine | Detected and Quantified | 1.6 (0.3-5.8) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 1.5 (0.1-8.7) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 1.0 (0.4-7.3) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | <50.12 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 3.2 (1.5-3.9) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | | Urine | Detected and Quantified | 2.8 (2.6-3.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.80 +/- 0.10 uM | Adult (>18 years old) | Both | Morphine treatment | | details | | Feces | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Both | CCD | | details | | Feces | Detected but not Quantified | Not Applicable | Adult (>18 years old) | Both | ICD | | details | | Urine | Detected and Quantified | 5.879 +/- 5.443 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected and Quantified | 8.512 +/- 4.226 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details | | Urine | Detected and Quantified | 6.21 +/- 4.38 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | | Urine | Detected and Quantified | 12.6 +/- 36.00 umol/mmol creatinine | Newborn (0-30 days old) | Both | Phenylketonuria | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Supradiaphragmatic malignancy |
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- Goudas LC, Langlade A, Serrie A, Matson W, Milbury P, Thurel C, Sandouk P, Carr DB: Acute decreases in cerebrospinal fluid glutathione levels after intracerebroventricular morphine for cancer pain. Anesth Analg. 1999 Nov;89(5):1209-15. [PubMed:10553836 ]
| | Phenylketonuria |
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- Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| DrugBank Metabolite ID | Not Available |
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| Phenol Explorer Compound ID | 577 |
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| Phenol Explorer Metabolite ID | Not Available |
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| FoodDB ID | FDB019021 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 9010 |
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| KEGG Compound ID | C03672 |
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| BioCyc ID | 4-HYDROXYPHENYLLACTATE |
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| BiGG ID | 2392410 |
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| Wikipedia Link | Not Available |
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| NuGOwiki Link | HMDB00755 |
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| Metagene Link | HMDB00755 |
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| METLIN ID | 5723 |
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| PubChem Compound | 9378 |
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| PDB ID | Not Available |
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| ChEBI ID | 17385 |
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| References |
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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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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
- Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
- Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]
- Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [PubMed:1249684 ]
- Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
- Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
- Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
- Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
- Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. [PubMed:6463026 ]
- Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
- (). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . . [ISBN:978-0079130358 ]
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