Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-13 11:48:29 UTC |
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Update Date | 2023-02-21 17:29:03 UTC |
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HMDB ID | HMDB0041929 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methoxyacetic acid |
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Description | Methoxyacetic acid, also known as 2-methoxyacetate or CH3OCH2COOH, belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. Methoxyacetic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make methoxyacetic acid a potential biomarker for the consumption of these foods. Methoxyacetic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Methoxyacetic acid. |
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Structure | InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5) |
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Synonyms | Value | Source |
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2-Methoxyacetic acid | ChEBI | CH3OCH2COOH | ChEBI | Methoxyethanoic acid | ChEBI | 2-Methoxyacetate | Generator | Methoxyethanoate | Generator | Methoxyacetate | Generator | Methoxy-acetic acid | HMDB | Methoxyacetic acid (acd/name 4.0) | HMDB | Methoxyacetic acid, calcium salt | HMDB | Methoxyacetic acid, sodium salt | HMDB |
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Chemical Formula | C3H6O3 |
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Average Molecular Weight | 90.0779 |
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Monoisotopic Molecular Weight | 90.031694058 |
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IUPAC Name | 2-methoxyacetic acid |
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Traditional Name | methoxyacetic acid |
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CAS Registry Number | 625-45-6 |
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SMILES | COCC(O)=O |
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InChI Identifier | InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5) |
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InChI Key | RMIODHQZRUFFFF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Carboxylic acids |
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Direct Parent | Carboxylic acids |
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Alternative Parents | |
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Substituents | - Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 7.7 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL at 20 °C | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized) | splash10-0002-9000000000-459a9fd6341faa2d6199 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized) | splash10-0002-9000000000-00eacd2cc9c79e884a7f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized) | splash10-0002-9000000000-459a9fd6341faa2d6199 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized) | splash10-0002-9000000000-00eacd2cc9c79e884a7f | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methoxyacetic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-052e-9000000000-88a8180e978a97b6d7d3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methoxyacetic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00dv-9100000000-17e4cc4c37ebe949ab03 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methoxyacetic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Positive-QTOF | splash10-0006-9000000000-06583265e77ad7b8df2b | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Positive-QTOF | splash10-0006-9000000000-4ff152447c2d0d3d8428 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Positive-QTOF | splash10-0006-9000000000-72838d342a353f12fdb0 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Negative-QTOF | splash10-000i-9000000000-e78337d19ef7afde9062 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Negative-QTOF | splash10-000i-9000000000-5f51eb18442219493d6f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Negative-QTOF | splash10-05fv-9000000000-cb363d2443dec92fb142 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Positive-QTOF | splash10-01ox-9000000000-aa894a83913446ac6644 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Positive-QTOF | splash10-0005-9000000000-e82059516011e327da53 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Positive-QTOF | splash10-0002-9000000000-cdb7c157d893f385dbdc | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Negative-QTOF | splash10-000i-9000000000-b333d7ca100349435b41 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Negative-QTOF | splash10-000i-9000000000-513de11c4773c144435e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Negative-QTOF | splash10-0006-9000000000-79a6253fbc0ac5ca9427 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB111678 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 11750 |
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KEGG Compound ID | Not Available |
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BioCyc ID | CPD-12993 |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 12251 |
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PDB ID | Not Available |
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ChEBI ID | 132098 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - de Jong E, Louisse J, Verwei M, Blaauboer BJ, van de Sandt JJ, Woutersen RA, Rietjens IM, Piersma AH: Relative developmental toxicity of glycol ether alkoxy acid metabolites in the embryonic stem cell test as compared with the in vivo potency of their parent compounds. Toxicol Sci. 2009 Jul;110(1):117-24. doi: 10.1093/toxsci/kfp083. Epub 2009 Apr 28. [PubMed:19401353 ]
- Starek-Swiechowicz B, Miranowicz-Dzierzawska K, Szymczak W, Budziszewska B, Starek A: Hematological effects of exposure to mixtures of selected ethylene glycol alkyl ethers in rats. Pharmacol Rep. 2012;64(1):166-78. [PubMed:22580533 ]
- Louisse J, Bai Y, Verwei M, van de Sandt JJ, Blaauboer BJ, Rietjens IM: Decrease of intracellular pH as possible mechanism of embryotoxicity of glycol ether alkoxyacetic acid metabolites. Toxicol Appl Pharmacol. 2010 Jun 1;245(2):236-43. doi: 10.1016/j.taap.2010.03.005. Epub 2010 Mar 11. [PubMed:20226807 ]
- Hermsen SA, van den Brandhof EJ, van der Ven LT, Piersma AH: Relative embryotoxicity of two classes of chemicals in a modified zebrafish embryotoxicity test and comparison with their in vivo potencies. Toxicol In Vitro. 2011 Apr;25(3):745-53. doi: 10.1016/j.tiv.2011.01.005. Epub 2011 Jan 14. [PubMed:21238576 ]
- Prasse C, Wagner M, Schulz R, Ternes TA: Oxidation of the antiviral drug acyclovir and its biodegradation product carboxy-acyclovir with ozone: kinetics and identification of oxidation products. Environ Sci Technol. 2012 Feb 21;46(4):2169-78. doi: 10.1021/es203712z. Epub 2012 Jan 31. [PubMed:22300376 ]
- Schaefer WR, Fischer L, Deppert WR, Hanjalic-Beck A, Seebacher L, Weimer M, Zahradnik HP: In vitro-Ishikawa cell test for assessing tissue-specific chemical effects on human endometrium. Reprod Toxicol. 2010 Aug;30(1):89-93. doi: 10.1016/j.reprotox.2010.02.002. Epub 2010 Feb 19. [PubMed:20172022 ]
- Bagchi G, Zhang Y, Waxman DJ: Impact of methoxyacetic acid on mouse Leydig cell gene expression. Reprod Biol Endocrinol. 2010 Jun 18;8:65. doi: 10.1186/1477-7827-8-65. [PubMed:20565877 ]
- Yang B, Sun H, Li W, Zhu C, Jian B, Hou W, Wang H, Yuan J, Yao B: Expression of Rap1 during germ cell development in the rat and its functional implications in 2-methoxyacetic acid-induced spermatocyte apoptosis. Urology. 2013 Mar;81(3):696.e1-8. doi: 10.1016/j.urology.2012.11.005. Epub 2013 Jan 3. [PubMed:23290149 ]
- Fromme H, Nitschke L, Boehmer S, Kiranoglu M, Goen T: Exposure of German residents to ethylene and propylene glycol ethers in general and after cleaning scenarios. Chemosphere. 2013 Mar;90(11):2714-21. doi: 10.1016/j.chemosphere.2012.11.051. Epub 2013 Jan 3. [PubMed:23290947 ]
- Robinson JF, van Beelen VA, Verhoef A, Renkens MF, Luijten M, van Herwijnen MH, Westerman A, Pennings JL, Piersma AH: Embryotoxicant-specific transcriptomic responses in rat postimplantation whole-embryo culture. Toxicol Sci. 2010 Dec;118(2):675-85. doi: 10.1093/toxsci/kfq292. Epub 2010 Sep 23. [PubMed:20864626 ]
- Elkin ND, Piner JA, Sharpe RM: Toxicant-induced leakage of germ cell-specific proteins from seminiferous tubules in the rat: relationship to blood-testis barrier integrity and prospects for biomonitoring. Toxicol Sci. 2010 Oct;117(2):439-48. doi: 10.1093/toxsci/kfq210. Epub 2010 Jul 12. [PubMed:20624998 ]
- Priyandoko D, Ishii T, Kaul SC, Wadhwa R: Ashwagandha leaf derived withanone protects normal human cells against the toxicity of methoxyacetic acid, a major industrial metabolite. PLoS One. 2011 May 4;6(5):e19552. doi: 10.1371/journal.pone.0019552. [PubMed:21573189 ]
- Teixido E, Pique E, Gomez-Catalan J, Llobet JM: Assessment of developmental delay in the zebrafish embryo teratogenicity assay. Toxicol In Vitro. 2013 Feb;27(1):469-78. doi: 10.1016/j.tiv.2012.07.010. Epub 2012 Aug 8. [PubMed:22898132 ]
- Bagchi G, Zhang Y, Stanley KA, Waxman DJ: Complex modulation of androgen responsive gene expression by methoxyacetic acid. Reprod Biol Endocrinol. 2011 Mar 31;9:42. doi: 10.1186/1477-7827-9-42. [PubMed:21453523 ]
- Henley DV, Mueller S, Korach KS: The short-chain fatty acid methoxyacetic acid disrupts endogenous estrogen receptor-alpha-mediated signaling. Environ Health Perspect. 2009 Nov;117(11):1702-6. doi: 10.1289/ehp.0900800. Epub 2009 Jun 16. [PubMed:20049119 ]
- Sui B, Yeh EA, Curran DP: Assignment of the structure of petrocortyne A by mixture syntheses of four candidate stereoisomers. J Org Chem. 2010 May 7;75(9):2942-54. doi: 10.1021/jo100115h. [PubMed:20394446 ]
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