| 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 | 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 | Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9000000000-f225de2de3540c3f50a4 | Spectrum | | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00di-9000000000-7de217d97b44f53aad82 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-9000000000-c968a24f0640b154325b | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-c968a24f0640b154325b | Spectrum | | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 1V, positive | splash10-004i-9000000000-fa715ee3ce9abbc94edb | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 2V, positive | splash10-004i-9000000000-ace3c5f526d28fd24de9 | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 3V, positive | splash10-004i-9000000000-ff7f922c2460adb6a10d | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 4V, positive | splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4 | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 5V, positive | splash10-004j-9000000000-e9c74e7df728e016450c | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 6V, positive | splash10-002b-9000000000-d0963403f3a8ff9e576d | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 7V, positive | splash10-002b-9000000000-9e1d6b2e2b889232d610 | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 8V, positive | splash10-0002-9000000000-e9824f68b2176db90d33 | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 9V, positive | splash10-000t-9000000000-02329982bc7150d972bf | Spectrum | | MS/MS | LC-MS/MS Spectrum - QqQ 10V, positive | splash10-000t-9000000000-216d8ece56b0a44e5289 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-d961c3c14ec415e3141e | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-9000000000-67f73be970ba9f885c4a | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-7445713a5fe347bbc8b8 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-26e13242443efc1aa846 | Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-6ba976b949118cd0a86a | Spectrum |
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| NMR | |
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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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