Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:05:44 UTC |
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Update date | 2020-09-17 15:38:20 UTC |
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Primary ID | FDB003298 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Hydroxyacetic acid |
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Description | Glycolic acid, also known as 2-hydroxyacetate or glycolate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. Glycolic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Glycolic acid exists in all living species, ranging from bacteria to humans. In humans, glycolic acid is involved in rosiglitazone metabolism pathway. Outside of the human body, Glycolic acid has been detected, but not quantified in, several different foods, such as sourdocks, pineappple sages, celeriacs, cloves, and feijoa. This could make glycolic acid a potential biomarker for the consumption of these foods. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. Glycolic acid is a potentially toxic compound. Glycolic acid, with regard to humans, has been found to be associated with several diseases such as transurethral resection of the prostate and biliary atresia; glycolic acid has also been linked to several inborn metabolic disorders including glutaric acidemia type 2, glycolic aciduria, and d-2-hydroxyglutaric aciduria. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. |
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CAS Number | 79-14-1 |
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Structure | |
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Synonyms | Synonym | Source |
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2-Hydroxyacetic acid | ChEBI | 2-Hydroxyethanoic acid | ChEBI | alpha-Hydroxyacetic acid | ChEBI | Glycollic acid | ChEBI | HOCH2COOH | ChEBI | Hydroxyacetic acid | ChEBI | Hydroxyethanoic acid | ChEBI | 2-Hydroxyacetate | Generator | 2-Hydroxyethanoate | Generator | a-Hydroxyacetate | Generator | a-Hydroxyacetic acid | Generator | alpha-Hydroxyacetate | Generator | Α-hydroxyacetate | Generator | Α-hydroxyacetic acid | Generator | Glycollate | Generator | Hydroxyacetate | Generator | Hydroxyethanoate | Generator | Glycolate | Generator | Glycocide | HMDB | GlyPure | HMDB | GlyPure 70 | HMDB | Sodium glycolate | HMDB | Glycolic acid, 2-(14)C-labeled | HMDB | Glycolic acid, 1-(14)C-labeled | HMDB | Glycolic acid, potassium salt | HMDB | Glycolic acid, monopotassium salt | HMDB | Glycolic acid, calcium salt | HMDB | Glycolic acid, monoammonium salt | HMDB | Glycolic acid, monolithium salt | HMDB | Glycolic acid, monosodium salt | HMDB | Potassium glycolate | HMDB | α-hydroxyacetic acid | biospider | 2-Hydroxy carboxylate | biospider | 2-Hydroxy carboxylic acid | biospider | Acetic acid, 2-hydroxy- | biospider | Acetic acid, hydroxy- (9CI) | biospider | Glycolic acid | db_source | α-hydroxyacetate | Generator | α-hydroxyacetic acid | Generator |
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Predicted Properties | |
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Chemical Formula | C2H4O3 |
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IUPAC name | 2-hydroxyacetic acid |
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InChI Identifier | InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) |
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InChI Key | AEMRFAOFKBGASW-UHFFFAOYSA-N |
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Isomeric SMILES | OCC(O)=O |
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Average Molecular Weight | 76.0514 |
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Monoisotopic Molecular Weight | 76.016043994 |
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Classification |
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Description | Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Alpha hydroxy acids and derivatives |
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Direct Parent | Alpha hydroxy acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-hydroxy acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Indirect biological role: Biological role: Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 31.59%; H 5.30%; O 63.11% | DFC |
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Melting Point | Mp 80° | DFC |
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Boiling Point | Bp 100° dec. | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | -1.11 | HANSCH,C ET AL. (1995) |
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Experimental pKa | pKa 3.82 | DFC |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-2885890e3bb8c015742f | 2014-09-20 | View Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-ed8b8e4a9e2556ea02e2 | Spectrum | GC-MS | Hydroxyacetic acid, 2 TMS, GC-MS Spectrum | splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8 | Spectrum | GC-MS | Hydroxyacetic acid, 2 TMS, GC-MS Spectrum | splash10-003r-2910000000-bd50bf5bab6f5327eaf4 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-cadf899be6b15d008330 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-001i-9000000000-e66ed28d8419895e0fb4 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-7f84fac3284d17fa3ba6 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-ed8b8e4a9e2556ea02e2 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-003r-2910000000-bd50bf5bab6f5327eaf4 | Spectrum | GC-MS | Hydroxyacetic acid, non-derivatized, GC-MS Spectrum | splash10-0002-0900000000-d724c85a3b30e3c2e4bc | Spectrum | Predicted GC-MS | Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0a7l-9000000000-1e9466549305eb20257b | Spectrum | Predicted GC-MS | Hydroxyacetic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-05i9-9520000000-5f0019fe63eb6e692109 | Spectrum | Predicted GC-MS | Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Hydroxyacetic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-9000000000-e942bdae1d60e5f5d649 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9000000000-f225de2de3540c3f50a4 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00di-9000000000-7de217d97b44f53aad82 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-9000000000-c968a24f0640b154325b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-c968a24f0640b154325b | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 1V, positive | splash10-004i-9000000000-fa715ee3ce9abbc94edb | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 2V, positive | splash10-004i-9000000000-ace3c5f526d28fd24de9 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 3V, positive | splash10-004i-9000000000-ff7f922c2460adb6a10d | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 4V, positive | splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 5V, positive | splash10-004j-9000000000-e9c74e7df728e016450c | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 6V, positive | splash10-002b-9000000000-d0963403f3a8ff9e576d | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 7V, positive | splash10-002b-9000000000-9e1d6b2e2b889232d610 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 8V, positive | splash10-0002-9000000000-e9824f68b2176db90d33 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 9V, positive | splash10-000t-9000000000-02329982bc7150d972bf | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - QqQ 10V, positive | splash10-000t-9000000000-216d8ece56b0a44e5289 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-d961c3c14ec415e3141e | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-9000000000-67f73be970ba9f885c4a | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6 | 2015-04-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-7445713a5fe347bbc8b8 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-26e13242443efc1aa846 | 2015-04-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-6ba976b949118cd0a86a | 2015-04-25 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 737 |
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ChEMBL ID | CHEMBL252557 |
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KEGG Compound ID | C03547 |
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Pubchem Compound ID | 757 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17497 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB03085 |
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HMDB ID | HMDB00115 |
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CRC / DFC (Dictionary of Food Compounds) ID | CVS61-P:CVS61-P |
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EAFUS ID | Not Available |
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Dr. Duke ID | GLYCOLLIC-ACID|GLYCOLIC-ACID |
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BIGG ID | 34090 |
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KNApSAcK ID | C00007461 |
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HET ID | GOA |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Glycolic_acid |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Glucose-6-phosphate 1-dehydrogenase | G6PD | P11413 | Phosphoglycolate phosphatase | PGP | A6NDG6 |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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