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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:29 UTC
Update Date2023-02-21 17:29:03 UTC
HMDB IDHMDB0041929
Secondary Accession Numbers
  • HMDB41929
Metabolite Identification
Common NameMethoxyacetic acid
DescriptionMethoxyacetic 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.
Structure
Data?1677000543
Synonyms
ValueSource
2-Methoxyacetic acidChEBI
CH3OCH2COOHChEBI
Methoxyethanoic acidChEBI
2-MethoxyacetateGenerator
MethoxyethanoateGenerator
MethoxyacetateGenerator
Methoxy-acetic acidHMDB
Methoxyacetic acid (acd/name 4.0)HMDB
Methoxyacetic acid, calcium saltHMDB
Methoxyacetic acid, sodium saltHMDB
Chemical FormulaC3H6O3
Average Molecular Weight90.0779
Monoisotopic Molecular Weight90.031694058
IUPAC Name2-methoxyacetic acid
Traditional Namemethoxyacetic acid
CAS Registry Number625-45-6
SMILES
COCC(O)=O
InChI Identifier
InChI=1S/C3H6O3/c1-6-2-3(4)5/h2H2,1H3,(H,4,5)
InChI KeyRMIODHQZRUFFFF-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point7.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mL at 20 °CNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility485 g/LALOGPS
logP-0.49ALOGPS
logP-0.4ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)3.83ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.1 m³·mol⁻¹ChemAxon
Polarizability8.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+115.8731661259
DarkChem[M-H]-110.54631661259
DeepCCS[M+H]+133.62830932474
DeepCCS[M-H]-130.83130932474
DeepCCS[M-2H]-167.43930932474
DeepCCS[M+Na]+141.88930932474
AllCCS[M+H]+124.332859911
AllCCS[M+H-H2O]+119.932859911
AllCCS[M+NH4]+128.432859911
AllCCS[M+Na]+129.632859911
AllCCS[M-H]-125.332859911
AllCCS[M+Na-2H]-130.032859911
AllCCS[M+HCOO]-135.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Methoxyacetic acidCOCC(O)=O1582.1Standard polar33892256
Methoxyacetic acidCOCC(O)=O827.2Standard non polar33892256
Methoxyacetic acidCOCC(O)=O796.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methoxyacetic acid,1TMS,isomer #1COCC(=O)O[Si](C)(C)C918.7Semi standard non polar33892256
Methoxyacetic acid,1TBDMS,isomer #1COCC(=O)O[Si](C)(C)C(C)(C)C1120.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized)splash10-0002-9000000000-459a9fd6341faa2d61992017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized)splash10-0002-9000000000-00eacd2cc9c79e884a7f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized)splash10-0002-9000000000-459a9fd6341faa2d61992018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Methoxyacetic acid EI-B (Non-derivatized)splash10-0002-9000000000-00eacd2cc9c79e884a7f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxyacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-9000000000-88a8180e978a97b6d7d32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxyacetic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dv-9100000000-17e4cc4c37ebe949ab032017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxyacetic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Positive-QTOFsplash10-0006-9000000000-06583265e77ad7b8df2b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Positive-QTOFsplash10-0006-9000000000-4ff152447c2d0d3d84282016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Positive-QTOFsplash10-0006-9000000000-72838d342a353f12fdb02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Negative-QTOFsplash10-000i-9000000000-e78337d19ef7afde90622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Negative-QTOFsplash10-000i-9000000000-5f51eb18442219493d6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Negative-QTOFsplash10-05fv-9000000000-cb363d2443dec92fb1422016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Positive-QTOFsplash10-01ox-9000000000-aa894a83913446ac66442021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Positive-QTOFsplash10-0005-9000000000-e82059516011e327da532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Positive-QTOFsplash10-0002-9000000000-cdb7c157d893f385dbdc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 10V, Negative-QTOFsplash10-000i-9000000000-b333d7ca100349435b412021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 20V, Negative-QTOFsplash10-000i-9000000000-513de11c4773c144435e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxyacetic acid 40V, Negative-QTOFsplash10-0006-9000000000-79a6253fbc0ac5ca94272021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111678
KNApSAcK IDNot Available
Chemspider ID11750
KEGG Compound IDNot Available
BioCyc IDCPD-12993
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12251
PDB IDNot Available
ChEBI ID132098
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]