You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information |
---|
Version | 4.0 |
---|
Status | Detected and Quantified |
---|
Creation Date | 2005-11-16 15:48:42 UTC |
---|
Update Date | 2020-11-09 23:14:02 UTC |
---|
HMDB ID | HMDB0000669 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | ortho-Hydroxyphenylacetic acid |
---|
Description | ortho-Hydroxyphenylacetic acid, also known as (o-hydroxyphenyl)acetate or 2-hydroxybenzeneacetic acid, is a member of the class of compounds known as 2(hydroxyphenyl)acetic acids. 2(Hydroxyphenyl)acetic acids are phenylacetic acids that carry a hydroxyl group at the 2-position. ortho-Hydroxyphenylacetic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). ortho-Hydroxyphenylacetic acid can be found in a number of food items such as natal plum, lemon verbena, half-highbush blueberry, and parsley, which makes ortho-hydroxyphenylacetic acid a potential biomarker for the consumption of these food products. ortho-Hydroxyphenylacetic acid can be found primarily in blood, feces, and urine. Moreover, ortho-hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. ortho-Hydroxyphenylacetic acid is a substrate of the enzyme oxidoreductases (EC 1.14.13.-) in the pathway styrene degradation (KEGG). ortho-Hydroxyphenylacetic acid is also a microbial metabolite. |
---|
Structure | |
---|
Synonyms | Value | Source |
---|
(O-Hydroxyphenyl)acetic acid | ChEBI | 2'-Hydroxyphenylacetic acid | ChEBI | 2-Hydroxybenzeneacetic acid | ChEBI | 2-Hydroxyphenylacetic acid | ChEBI | O-Hydroxyphenylacetic acid | ChEBI | (O-Hydroxyphenyl)acetate | Generator | 2'-Hydroxyphenylacetate | Generator | 2-Hydroxybenzeneacetate | Generator | 2-Hydroxyphenylacetate | Generator | O-Hydroxyphenylacetate | Generator | Ortho-hydroxyphenylacetate | Generator | (2-Hydroxyphenyl)acetate | HMDB | (2-Hydroxyphenyl)acetic acid | HMDB | (O-Hydroxyphenyl)-acetate | HMDB | (O-Hydroxyphenyl)-acetic acid | HMDB | 2-HPAA | HMDB | Hydroxyphenylacetate | HMDB | Hydroxyphenylacetic acid | HMDB | O-Hydroxyphenyl acetic acid | HMDB | Ortho-hydroxyphenylacetic acid | MeSH |
|
---|
Chemical Formula | C8H8O3 |
---|
Average Molecular Weight | 152.1473 |
---|
Monoisotopic Molecular Weight | 152.047344122 |
---|
IUPAC Name | 2-(2-hydroxyphenyl)acetic acid |
---|
Traditional Name | o-hydroxyphenylacetic acid |
---|
CAS Registry Number | 614-75-5 |
---|
SMILES | OC(=O)CC1=C(O)C=CC=C1 |
---|
InChI Identifier | InChI=1S/C8H8O3/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4,9H,5H2,(H,10,11) |
---|
InChI Key | CCVYRRGZDBSHFU-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | belongs to the class of organic compounds known as 2(hydroxyphenyl)acetic acids. These are phenylacetic acids that carry a hydroxyl group at the 2-position. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Benzene and substituted derivatives |
---|
Sub Class | Phenylacetic acids |
---|
Direct Parent | 2(hydroxyphenyl)acetic acids |
---|
Alternative Parents | |
---|
Substituents | - 2(hydroxyphenyl)acetic acid
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homomonocyclic compound
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Biological location: Source: |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | 145 - 147 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 44 mg/mL | Not Available | LogP | 0.85 | HANSCH,C ET AL. (1995) |
|
---|
Predicted Properties | |
---|
Spectra |
---|
| Spectrum Type | Description | Splash Key | View |
---|
GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0920000000-ca3851c9928227913a97 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-0w29-1970000000-de8569a7d279b97680a4 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0960000000-1018d2254ff44190f41a | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0920000000-ca3851c9928227913a97 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0w29-1970000000-de8569a7d279b97680a4 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4i-1900000000-0a090cff04cd89d36022 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-004i-6930000000-1903392fd44f061e93eb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-0900000000-c0378212353f9c247060 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0a4i-0900000000-2e1d10888e4b882683d4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0a4i-1900000000-87d962f7cd6aa06c4832 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0a4i-0900000000-e7c99cfd03a6c025cf2c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-6a2b0b911cb357174c27 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-1900000000-06436376438e44718bb7 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-056r-9300000000-19f4bd2f314d6c0b49bd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0zfr-0900000000-c00a2e1956529eb24b43 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0pc0-0900000000-a60511b0d00662895871 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a59-4900000000-68a51d2b15b093ce1545 | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
|
---|
Biological Properties |
---|
Cellular Locations | Not Available |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| |
Blood | Detected and Quantified | 0.287 +/- 0.033 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.213 +/- 0.021 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.265 +/- 0.032 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.329 +/- 0.064 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.228 +/- 0.019 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.207 +/- 0.023 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 0.213 +/- 0.026 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected and Quantified | 2.281 +/- 2.091 uM | Adult (>18 years old) | Male | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Female | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.76 +/- 0.457 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.38-0.72 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 22.48 +/- 16.25 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.36-0.53 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Consuming polyphenols described by Phenol-Explorer entry 953 | | details | Urine | Detected and Quantified | <20 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.594 +/- 0.372 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 0.966 +/- 1.338 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 1.189 +/- 0.966 umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 2.0 (0.9-4.5) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 7.71 +/- 3.65 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 2.9 (1.4-3.7) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
|
---|
Abnormal Concentrations |
---|
| |
Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | Urine | Detected and Quantified | 0.643 +/- 0.815 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 0.603 +/- 0.339 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Gastroesophageal reflux disease | | details | Urine | Detected and Quantified | 1.226 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | 151.592 +/- 98.0886 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 48.301 +/- 20.0636 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 97.346 +/- 59.448 umol/mmol creatinine | Children (1-13 years old) | Both | Phenylketonuria | | details | Urine | Detected and Quantified | 36.53 +/- 39.59 umol/mmol creatinine | Newborn (0-30 days old) | Both | Phenylketonuria | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Irritable bowel syndrome |
---|
- Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
| Phenylketonuria |
---|
- 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 ]
- Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
| Eosinophilic esophagitis |
---|
- (). Mordechai, Hien, and David S. Wishart. .
|
|
---|
Associated OMIM IDs | |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB012331 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 11476 |
---|
KEGG Compound ID | C05852 |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | 5639 |
---|
PubChem Compound | 11970 |
---|
PDB ID | Not Available |
---|
ChEBI ID | 28478 |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | 2HYOXPLAC |
---|
MarkerDB ID | MDB00000211 |
---|
References |
---|
Synthesis Reference | Levine, Joseph; Eble, T. E.; Fischbach, Henry. Preparation of o-hydroxyphenylacetic acid. Journal of the American Chemical Society (1948), 70 1930. |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - Greenslade D, Havler ME, Humphrey MJ, Jordan BJ, Rance MJ: Species differences in the metabolism and excretion of fenclofenac. Xenobiotica. 1980 Oct;10(10):753-60. [PubMed:7456491 ]
- Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [PubMed:357810 ]
- Langenbeck U, Behbehani A, Mench-Hoinowski A, Petersen M: Absence of a significant renal threshold for two aromatic acids in phenylketonuric children over two years of age. Eur J Pediatr. 1980 Aug;134(2):115-8. [PubMed:7439195 ]
- Watson DG, McGhee CN, Midgley JM, Zhou P, Doig WM: Determination of acidic metabolites of biogenic amines in human aqueous humour by gas chromatography--negative ion chemical ionisation mass spectrometry. J Neurochem. 1992 Jan;58(1):116-20. [PubMed:1727423 ]
|
---|