Methoxyacetic acid (CHEM013165)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 04:08:51 UTC
Update Date2016-11-09 01:14:44 UTC
Accession NumberCHEM013165
Identification
Common NameMethoxyacetic acid
ClassSmall Molecule
DescriptionA monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a methoxy group.
Contaminant Sources
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass90.078 g/mol
Monoisotopic Mass90.032 g/mol
CAS Registry Number625-45-6
IUPAC Name2-methoxyacetic acid
Traditional Namemethoxyacetic acid
SMILESCOCC(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-459a9fd6341faa2d6199Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-00eacd2cc9c79e884a7fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-459a9fd6341faa2d6199Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-00eacd2cc9c79e884a7fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052e-9000000000-88a8180e978a97b6d7d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dv-9100000000-17e4cc4c37ebe949ab03Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-06583265e77ad7b8df2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4ff152447c2d0d3d8428Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-72838d342a353f12fdb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-e78337d19ef7afde9062Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-5f51eb18442219493d6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fv-9000000000-cb363d2443dec92fb142Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-9000000000-aa894a83913446ac6644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-9000000000-e82059516011e327da53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-cdb7c157d893f385dbdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-b333d7ca100349435b41Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-513de11c4773c144435eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-79a6253fbc0ac5ca9427Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0041929
FooDB IDFDB111678
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12993
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID11750
ChEBI ID132098
PubChem Compound ID12251
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23290149
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23290947
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24798094
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25606576
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=26001161
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=26006246
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=26802500
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. 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.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.