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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-11-09 23:12:05 UTC |
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HMDB ID | HMDB0000115 |
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Secondary Accession Numbers | - HMDB0003035
- HMDB00115
- HMDB03035
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Metabolite Identification |
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Common Name | Glycolic acid |
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Description | Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). This colourless, odourless, and hygroscopic crystalline solid is highly soluble in water. Due to its excellent capability to penetrate skin, glycolic acid is often used in skin care products, most often as a chemical peel. It may reduce wrinkles, acne scarring, and hyperpigmentation and improve many other skin conditions, including actinic keratosis, hyperkeratosis, and seborrheic keratosis. 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. This allows the outer skin to dissolve, revealing the underlying skin. It is thought that this is due to the reduction of calcium ion concentrations in the epidermis and the removal of calcium ions from cell adhesions, leading to desquamation. Glycolic acid is a known inhibitor of tyrosinase. This can suppress melanin formation and lead to a lightening of skin colour. Acute doses of glycolic acid on skin or eyes leads to local effects that are typical of a strong acid (e.g. dermal and eye irritation). Glycolate is a nephrotoxin if consumed orally. A nephrotoxin is a compound that causes damage to the kidney and kidney tissues. Glycolic acid's renal toxicity is due to its metabolism to oxalic acid. Glycolic and oxalic acid, along with excess lactic acid, are responsible for the anion gap metabolic acidosis. Oxalic acid readily precipitates with calcium to form insoluble calcium oxalate crystals. Renal tissue injury is caused by widespread deposition of oxalate crystals and the toxic effects of glycolic acid. Glycolic acid does exhibit some inhalation toxicity and can cause respiratory, thymus, and liver damage if present in very high levels over long periods of time. Elevated glycolic acid without elevated oxalic acid is most likely a result of GI yeast overgrowth (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). (http://drweyrich.weyrich.com/labs/oat.html). Glycolic acid has also been found to be a metabolite in Acetobacter, Acidithiobacillus, Alcaligenes, Corynebacterium, Cryptococcus, Escherichia, Gluconobacter, Kluyveromyces, Leptospirillum, Pichia, Rhodococcus, Rhodotorula and Saccharomyces (PMID: 11758919 ; PMID: 26360870 ; PMID: 14390024 ). |
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Structure | |
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Synonyms | Value | 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 |
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Chemical Formula | C2H4O3 |
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Average Molecular Weight | 76.0514 |
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Monoisotopic Molecular Weight | 76.016043994 |
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IUPAC Name | 2-hydroxyacetic acid |
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Traditional Name | glycolic acid |
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CAS Registry Number | 79-14-1 |
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SMILES | OCC(O)=O |
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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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Chemical Taxonomy |
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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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 75 - 80 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | -1.11 | HANSCH,C ET AL. (1995) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0002-0900000000-ed8b8e4a9e2556ea02e2 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-003r-2910000000-bd50bf5bab6f5327eaf4 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001i-9000000000-cadf899be6b15d008330 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-001i-9000000000-e66ed28d8419895e0fb4 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0002-0900000000-7f84fac3284d17fa3ba6 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-ed8b8e4a9e2556ea02e2 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00dj-9600000000-8bafc88c7bf4e90fb5e8 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-003r-2910000000-bd50bf5bab6f5327eaf4 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0002-0900000000-d724c85a3b30e3c2e4bc | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a7l-9000000000-1e9466549305eb20257b | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-05i9-9520000000-5f0019fe63eb6e692109 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004i-9000000000-e942bdae1d60e5f5d649 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-00di-9000000000-f225de2de3540c3f50a4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-00di-9000000000-7de217d97b44f53aad82 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-004i-9000000000-c968a24f0640b154325b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-00di-9000000000-88af2b259f82cd1d8938 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-004i-9000000000-c968a24f0640b154325b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0059-9000000000-1dfacf30bf94ce3bf8bb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 1V, positive | splash10-004i-9000000000-fa715ee3ce9abbc94edb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 2V, positive | splash10-004i-9000000000-ace3c5f526d28fd24de9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 3V, positive | splash10-004i-9000000000-ff7f922c2460adb6a10d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 4V, positive | splash10-004i-9000000000-1d63aaaf9cbc6d3bb3b4 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 5V, positive | splash10-004j-9000000000-e9c74e7df728e016450c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 6V, positive | splash10-002b-9000000000-d0963403f3a8ff9e576d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 7V, positive | splash10-002b-9000000000-9e1d6b2e2b889232d610 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 8V, positive | splash10-0002-9000000000-e9824f68b2176db90d33 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 9V, positive | splash10-000t-9000000000-02329982bc7150d972bf | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 10V, positive | splash10-000t-9000000000-216d8ece56b0a44e5289 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-9000000000-d961c3c14ec415e3141e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-9000000000-67f73be970ba9f885c4a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-f2ccf0b88e0ad65ed4c6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-9000000000-7445713a5fe347bbc8b8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-26e13242443efc1aa846 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-6ba976b949118cd0a86a | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-001i-9000000000-2885890e3bb8c015742f | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Sweat
- Urine
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Tissue Locations | - Bladder
- Epidermis
- Fibroblasts
- Liver
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 50-123 uM | Adolescent (13-18 years old) | Female | Normal | | details | Blood | Detected and Quantified | 34 uM | Adult (>18 years old) | Female | Normal | | details | Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 7.9 +/- 2.4 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 7.8 +/- 1.7 uM | Adult (>18 years old) | Both | Normal | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 54.0 +/- 50.0 uM | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Both | Normal | | details | Feces | Detected and Quantified | 174.882 +/- 63.115 nmol/g wet feces | Not Specified | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | 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) | Both | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 8.64 +/- 3.09 uM | Adult (>18 years old) | Male | Normal | | details | Saliva | Detected and Quantified | 9.67 +/- 3.35 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected and Quantified | 10.7 +/- 1.79 uM | Adult (>18 years old) | Female | Normal | | details | Saliva | Detected and Quantified | 10.9 +/- 2.45 uM | Adult (>18 years old) | Not Specified | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected and Quantified | 21.65 +/- 13.0 uM | Adult (>18 years old) | Both | Normal | | details | Sweat | Detected but not Quantified | Not Quantified | Adult | Both | Normal | | details | Urine | Detected and Quantified | 20.813-169.475 umol/mmol creatinine | Children (1-13 years old) | Male | Normal | | details | Urine | Detected and Quantified | 68.385-169.475 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | 10-24.7 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 10.5-29.0 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | Urine | Detected and Quantified | 13-27.4 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected and Quantified | 14.2-33.9 umol/mmol creatinine | Infant (0-1 year old) | Female | Normal | | details | Urine | Detected and Quantified | 67.9 (36.0-324.4) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 23-53 umol/mmol creatinine | Adult (>18 years old) | Female | Normal | | details | Urine | Detected and Quantified | <104.0638 umol/mmol creatinine | Children (1 - 13 years old) | Male | Normal | | details | Urine | Detected and Quantified | <193.261 umol/mmol creatinine | Infant (0-1 year old) | Male | Normal | | details | Urine | Detected and Quantified | 30.0 (15.8-52.6) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 41.6 (3.7-122.1) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 38.10 +/- 27.35 umol/mmol creatinine | Children (1-13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <54.91 umol/mmol creatinine | Children (1 - 18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 64.0 (21.0-107.0) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 32.8 (8.8-71.6) umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 248.5(72.0-425.0) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 169.5 (46.0-293.0) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 128.0 (48.0-208.0) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 110.0 (34.0-186.0) umol/mmol creatinine | Adolescent (13-18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 35 (18-55) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 36.667 (13.333-52.667) umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 26-47 umol/mmol creatinine | Adult (>18 years old) | Male | Normal | | details | Urine | Detected and Quantified | 39.4 (2.9-78.1) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 190-480 umol/mmol creatinine | Newborn (0-30 days old) | Both | Normal | | details | Urine | Detected and Quantified | 74.257 +/- 48.676 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0-229 umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details | Urine | Detected and Quantified | 39.6 (16.7-89.1) umol/mmol creatinine | Infant (0-1 year old) | Both | Normal | | details | Urine | Detected and Quantified | 77.1 (33.1-122.0) umol/mmol creatinine | Children (1-13 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0 uM | Adult (>18 years old) | Female | Branched-chain Keto Acid Dehydrogenase Kinase Deficiency | | details | Blood | Detected and Quantified | 0 uM | Adolescent (13-18 years old) | Female | Branched-chain Keto Acid Dehydrogenase Kinase Deficiency | | details | Blood | Detected and Quantified | 7.3 +/- 10.1 uM | Adult (>18 years old) | Both | Hemodialysis | | details | Blood | Detected and Quantified | 0.6 +/- 2.3 uM | Adult (>18 years old) | Both | Hemodialysis | | details | Blood | Detected and Quantified | 48.0 (40.0 - 56.0) uM | Adult (>18 years old) | Both | Ethylene Glycol Poisoning | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 1868 uM | Adult (>18 years old) | Both | Transurethral prostatectomy syndrome | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal cancer | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details | Urine | Detected and Quantified | <20.813 umol/mmol creatinine | Children (1-13 years old) | Male | Glutaric acidemia type 2 | | details | Urine | Detected and Quantified | 52.0319-156.0957 umol/mmol creatinine | Adult (>18 years old) | Female | Glutaric acidemia type 2 | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details | Urine | Detected and Quantified | 5.947 umol/mmol creatinine | Infant (0-1 year old) | Male | Fumarase deficiency | | details | Urine | Detected and Quantified | 6.667 umol/mmol creatinine | Children (1 - 13 years old) | Male | D-2-Hydroxyglutaric aciduria | | details | Urine | Detected and Quantified | 163.529 umol/mmol creatinine | Children (1 - 13 years old) | Male | D-2-Hydroxyglutaric aciduria | | details | Urine | Detected and Quantified | 341.924 umol/mmol creatinine | Children (1 - 13 years old) | Male | D-2-Hydroxyglutaric aciduria | | details | Urine | Detected and Quantified | 359.333 umol/mmol creatinine | Adult (>18 years old) | Male | Primary hyperoxaluria I | | details | Urine | Detected and Quantified | 280.667-1946 umol/mmol creatinine | Children (1-13 years old) | Both | Primary hyperoxaluria I | | details | Urine | Detected and Quantified | 23.0 +/- 14.0 umol/mmol creatinine | Adult (>18 years old) | Both | Lung cancer | | details | Urine | Detected and Quantified | 0.40 +/- 0.36 umol/mmol creatinine | Adult (>18 years old) | Both | Biliary atresia | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Schizophrenia | | details | Urine | Detected and Quantified | 47.009 +/- 25.964 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details | Urine | Detected and Quantified | >229 umol/mmol creatinine | Children (1-13 years old) | Both | Glycolic aciduria | | details |
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Associated Disorders and Diseases |
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Disease References | Ethylene glycol poisoning |
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- Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. [PubMed:3337119 ]
| Hemodialysis |
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- Ogawa Y, Machida N, Jahana M, Gakiya M, Chinen Y, Oda M, Morozumi M, Sugaya K: Major factors modulating the serum oxalic acid level in hemodialysis patients. Front Biosci. 2004 Sep 1;9:2901-8. [PubMed:15353324 ]
| Branched-chain Keto Acid Dehydrogenase Kinase Deficiency |
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- Novarino G, El-Fishawy P, Kayserili H, Meguid NA, Scott EM, Schroth J, Silhavy JL, Kara M, Khalil RO, Ben-Omran T, Ercan-Sencicek AG, Hashish AF, Sanders SJ, Gupta AR, Hashem HS, Matern D, Gabriel S, Sweetman L, Rahimi Y, Harris RA, State MW, Gleeson JG: Mutations in BCKD-kinase lead to a potentially treatable form of autism with epilepsy. Science. 2012 Oct 19;338(6105):394-7. doi: 10.1126/science.1224631. Epub 2012 Sep 6. [PubMed:22956686 ]
| Transurethral resection of the prostate |
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- Perier C, Mahul P, Molliex S, Auboyer C, Frey J: Progressive changes in glycine and glycine derivatives in plasma and cerebrospinal fluid after transurethral prostatic resection. Clin Chem. 1990 Dec;36(12):2152-3. [PubMed:2253377 ]
| Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Lung Cancer |
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- Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2009 Jan;37(Database issue):D603-10. doi: 10.1093/nar/gkn810. Epub 2008 Oct 25. [PubMed:18953024 ]
| Biliary atresia |
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- Nittono H, Obinata K, Nakatsu N, Watanabe T, Niijima S, Sasaki H, Arisaka O, Kato H, Yabuta K, Miyano T: Sulfated and nonsulfated bile acids in urine of patients with biliary atresia: analysis of bile acids by high-performance liquid chromatography. J Pediatr Gastroenterol Nutr. 1986 Jan;5(1):23-9. [PubMed:3944741 ]
| Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
| Schizophrenia |
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- Yang J, Chen T, Sun L, Zhao Z, Qi X, Zhou K, Cao Y, Wang X, Qiu Y, Su M, Zhao A, Wang P, Yang P, Wu J, Feng G, He L, Jia W, Wan C: Potential metabolite markers of schizophrenia. Mol Psychiatry. 2013 Jan;18(1):67-78. doi: 10.1038/mp.2011.131. Epub 2011 Oct 25. [PubMed:22024767 ]
| Fumarase deficiency |
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- Bastug O, Kardas F, Ozturk MA, Halis H, Memur S, Korkmaz L, Tag Z, Gunes T: A rare cause of opistotonus; fumaric aciduria: The first case presentation in Turkey. Turk Pediatri Ars. 2014 Mar 1;49(1):74-6. doi: 10.5152/tpa.2014.442. eCollection 2014 Mar. [PubMed:26078636 ]
| D-2-hydroxyglutaric aciduria |
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- Chalmers RA, Lawson AM, Watts RW, Tavill AS, Kamerling JP, Hey E, Ogilvie D: D-2-hydroxyglutaric aciduria: case report and biochemical studies. J Inherit Metab Dis. 1980;3(1):11-5. [PubMed:6774165 ]
| Primary hyperoxaluria I |
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- Holmgren G, Hornstrom T, Johansson S, Samuelson G: Primary hyperoxaluria (glycolic acid variant): a clinical and genetical investigation of eight cases. Ups J Med Sci. 1978;83(1):65-70. [PubMed:705974 ]
| Glycolic aciduria |
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- Coulter-Mackie MB, White CT, Lange D, et al. (2002). Primary Hyperoxaluria Type 1. 2002 Jun 19 [Updated 2014 Jul 17]. In: Adam MP, Ardinger HH, Pagon RA, et al., editors. GeneReviews® [Internet]. Seattle (WA): University of Washington, Seattle; 1993-2017. Available from: https://www.ncbi.nlm.nih.gov/books/NBK1283/. University of Washington, Seattle.
| Glutaric acidemia type 2 |
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- Chlebeck PT, Milliner DS, Smith LH: Long-term prognosis in primary hyperoxaluria type II (L-glyceric aciduria). Am J Kidney Dis. 1994 Feb;23(2):255-9. [PubMed:8311084 ]
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Associated OMIM IDs | - 614923 (Branched-chain Keto Acid Dehydrogenase Kinase Deficiency)
- 114500 (Colorectal cancer)
- 211980 (Lung Cancer)
- 210500 (Biliary atresia)
- 610247 (Eosinophilic esophagitis)
- 181500 (Schizophrenia)
- 606812 (Fumarase deficiency)
- 600721 (D-2-hydroxyglutaric aciduria)
- 259900 (Glycolic aciduria)
- 231680 (Glutaric acidemia type 2)
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External Links |
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DrugBank ID | DB03085 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003298 |
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KNApSAcK ID | C00007461 |
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Chemspider ID | 737 |
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KEGG Compound ID | C03547 |
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BioCyc ID | GLYCOLLATE |
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BiGG ID | 34090 |
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Wikipedia Link | Glycolic_acid |
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METLIN ID | 3219 |
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PubChem Compound | 757 |
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PDB ID | Not Available |
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ChEBI ID | 17497 |
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Food Biomarker Ontology | Not Available |
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VMH ID | GLYCLT |
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MarkerDB ID | MDB00013417 |
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References |
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Synthesis Reference | Witzemann, Edgar J. Preparation of glycollic acid. Journal of the American Chemical Society (1917), 39 109-12. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Horikoshi T, Matsumoto M, Usuki A, Igarashi S, Hikima R, Uchiwa H, Hayashi S, Brysk MM, Ichihashi M, Funasaka Y: Effects of glycolic acid on desquamation-regulating proteinases in human stratum corneum. Exp Dermatol. 2005 Jan;14(1):34-40. [PubMed:15660917 ]
- Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
- DiNardo JC, Grove GL, Moy LS: Clinical and histological effects of glycolic acid at different concentrations and pH levels. Dermatol Surg. 1996 May;22(5):421-4. [PubMed:8634803 ]
- Marangella M, Petrarulo M, Bianco O, Vitale C, Finocchiaro P, Linari F: Glycolate determination detects type I primary hyperoxaluria in dialysis patients. Kidney Int. 1991 Jan;39(1):149-54. [PubMed:2002628 ]
- Tsiafoulis CG, Prodromidis MI, Karayannis MI: Development of amperometric biosensors for the determination of glycolic acid in real samples. Anal Chem. 2002 Jan 1;74(1):132-9. [PubMed:11795781 ]
- Porter WH, Rutter PW, Yao HH: Simultaneous determination of ethylene glycol and glycolic acid in serum by gas chromatography-mass spectrometry. J Anal Toxicol. 1999 Nov-Dec;23(7):591-7. [PubMed:10595845 ]
- Jacobsen D, Hewlett TP, Webb R, Brown ST, Ordinario AT, McMartin KE: Ethylene glycol intoxication: evaluation of kinetics and crystalluria. Am J Med. 1988 Jan;84(1):145-52. [PubMed:3337119 ]
- 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 ]
- Bernstein EF, Lee J, Brown DB, Yu R, Van Scott E: Glycolic acid treatment increases type I collagen mRNA and hyaluronic acid content of human skin. Dermatol Surg. 2001 May;27(5):429-33. [PubMed:11359487 ]
- Leumann EP, Dietl A, Matasovic A: Urinary oxalate and glycolate excretion in healthy infants and children. Pediatr Nephrol. 1990 Sep;4(5):493-7. [PubMed:2242313 ]
- Booth ED, Dofferhoff O, Boogaard PJ, Watson WP: Comparison of the metabolism of ethylene glycol and glycolic acid in vitro by precision-cut tissue slices from female rat, rabbit and human liver. Xenobiotica. 2004 Jan;34(1):31-48. [PubMed:14742135 ]
- Mahul P, Molliex S, Auboyer C, Levigne F, Jospe R, Dumont A, Gilloz A: [Neurotoxic role of glycocolle and derivatives in transurethral resection of the prostate]. Ann Fr Anesth Reanim. 1993;12(5):512-4. [PubMed:8311360 ]
- Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. [PubMed:8412012 ]
- Marangella M, Petrarulo M, Vitale C, Cosseddu D, Linari F: Plasma and urine glycolate assays for differentiating the hyperoxaluria syndromes. J Urol. 1992 Sep;148(3 Pt 2):986-9. [PubMed:1507356 ]
- Effendy I, Kwangsukstith C, Lee JY, Maibach HI: Functional changes in human stratum corneum induced by topical glycolic acid: comparison with all-trans retinoic acid. Acta Derm Venereol. 1995 Nov;75(6):455-8. [PubMed:8651024 ]
- Pien K, van Vlem B, van Coster R, Dacremont G, Piette M: An inherited metabolic disorder presenting as ethylene glycol intoxication in a young adult. Am J Forensic Med Pathol. 2002 Mar;23(1):96-100. [PubMed:11953504 ]
- Dietzen DJ, Wilhite TR, Kenagy DN, Milliner DS, Smith CH, Landt M: Extraction of glyceric and glycolic acids from urine with tetrahydrofuran: utility in detection of primary hyperoxaluria. Clin Chem. 1997 Aug;43(8 Pt 1):1315-20. [PubMed:9267307 ]
- Newman N, Newman A, Moy LS, Babapour R, Harris AG, Moy RL: Clinical improvement of photoaged skin with 50% glycolic acid. A double-blind vehicle-controlled study. Dermatol Surg. 1996 May;22(5):455-60. [PubMed:8634809 ]
- Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
- Porter WH, Rutter PW, Bush BA, Pappas AA, Dunnington JE: Ethylene glycol toxicity: the role of serum glycolic acid in hemodialysis. J Toxicol Clin Toxicol. 2001;39(6):607-15. [PubMed:11762669 ]
- Kataoka M, Sasaki M, Hidalgo AR, Nakano M, Shimizu S: Glycolic acid production using ethylene glycol-oxidizing microorganisms. Biosci Biotechnol Biochem. 2001 Oct;65(10):2265-70. doi: 10.1271/bbb.65.2265. [PubMed:11758919 ]
- Becker J, Lange A, Fabarius J, Wittmann C: Top value platform chemicals: bio-based production of organic acids. Curr Opin Biotechnol. 2015 Dec;36:168-75. doi: 10.1016/j.copbio.2015.08.022. Epub 2015 Sep 8. [PubMed:26360870 ]
- MARTIN SM, STEEL R: Effect of phosphate on production of organic acids by Aspergillus niger. Can J Microbiol. 1955 Jun;1(6):470-2. [PubMed:14390024 ]
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