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Record Information
Version1.0
Creation Date2016-09-30 22:18:51 UTC
Update Date2019-03-05 23:27:24 UTC
MCDB ID BMDB00042
Secondary Accession NumbersNone
Metabolite Identification
Common NameAcetic acid
DescriptionAcetic acid, also known as glacial acetate or vinegar, 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. Acetic acid is a drug which is used to treat infections in the ear canal. Acetic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Acetic acid exists in all living species, ranging from bacteria to humans. Acetic acid has been found to be associated with several diseases known as colorectal cancer, gout, and perillyl alcohol administration for cancer treatment; also acetic acid has been linked to several inborn metabolic disorders including celiac disease and phenylketonuria.
Structure
Thumb
Synonyms
ValueSource
Acide acetiqueChEBI
AcOHChEBI
CH3-COOHChEBI
CH3CO2HChEBI
e 260ChEBI
e-260ChEBI
e260ChEBI
EssigsaeureChEBI
Ethanoic acidChEBI
Ethoic acidChEBI
Ethylic acidChEBI
HOAcChEBI
INS no. 260ChEBI
MeCO2hChEBI
MeCOOHChEBI
Methanecarboxylic acidChEBI
Glacial acetic acidKegg
AcetasolKegg
EthanoateGenerator
EthoateGenerator
EthylateGenerator
MethanecarboxylateGenerator
Glacial acetateGenerator
AcetateGenerator
Kyselina octovaHMDB
VinegarHMDB
Vinegar acidHMDB
Acid, aceticHMDB
Acetic acid glacialHMDB
Acid glacial, aceticHMDB
Acid, glacial aceticHMDB
Acetic acid, glacialHMDB
Glacial, acetic acidHMDB
Chemical FormulaC2H4O2
Average Molecular Weight60.052
Monoisotopic Molecular Weight60.021129372
IUPAC Nameacetic acid
Traditional Nameacetic acid
CAS Registry Number64-19-7
SMILES
CC(O)=O
InChI Identifier
InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
InChI KeyQTBSBXVTEAMEQO-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
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.6 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-0.17HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP-0.12ALOGPS
logP-0.22ChemAxon
logS0.73ALOGPS
pKa (Strongest Acidic)4.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity12.64 m³·mol⁻¹ChemAxon
Polarizability5.34 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-a9a21f72ec25efbc1650JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0007-9000000000-a9a21f72ec25efbc1650JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9000000000-b96ad978047d68715939JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9100000000-8154631f77f485ee31b9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-9000000000-044b361cb9f5775c43feJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01ox-9000000000-6437eb5f6a38c054dc37JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-0505dfa8ee07a18a3ef3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0007-9000000000-a0d65dd4e056c1482aaaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-9000000000-a845ea0157abb3d7783bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-42ec023f024176a1c692JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-2bbab52cd9d076b89b2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-fb6d2f6298dd5bc37c2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-bc47c47ade16451259c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a845ea0157abb3d7783bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-42ec023f024176a1c692JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-2bbab52cd9d076b89b2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-fb6d2f6298dd5bc37c2eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-bc47c47ade16451259c7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-528a9b0672006e635695JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9000000000-a784dfc5bd03549bc072JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9000000000-b71ac391a2b191d6ef01JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-034375837c4c93ddf819JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-f031d1f9ac695f944bbdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-64f8448a12a6d78d84e4JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-01oy-9000000000-181ada67a3e5798d4419JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Concentrations
StatusValueReferenceDetails
Detected and Quantified14 - 35 uM details
Detected and Quantified108 - 701 uM details
Detected and Quantified13 - 37 uM details
Detected and Quantified13 - 37 uM details
Detected and Quantified28 +/- 2 uMFree fatty acid details
Detected and Quantified30 +/- 2 uMFree fatty acid details
Detected and Quantified31 +/- 2 uMFree fatty acid details
Detected and Quantified33 +/- 3 uMFree fatty acid details
Detected and Quantified42 +/- 10 uMFree fatty acid details
Detected and Quantified48 +/- 12.4 uMFree fatty acid details
Detected and Quantified71 +/- 42 uMFree fatty acid details
Detected and Quantified97 +/- 4 uMFree fatty acid
  • Catrienus De Jong...
details
Detected and Quantified6.8 (2.6 - 7.7) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified5.7 (2.8 - 7.6) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified9.6 (2.6 - 23) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified95 (11 - 199) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified135 +/- 2 uMFree fatty acid
  • Catrienus De Jong...
details
Detected and Quantified38 +/- 1 uMFree fatty acid details
Detected and Quantified37 +/- 1 uMFree fatty acid details
Detected and Quantified46 +/- 1 uMFree fatty acid details
Detected and Quantified43 +/- 1 uMFree fatty acid details
HMDB IDHMDB0000042
DrugBank IDDB03166
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008299
KNApSAcK IDC00001176
Chemspider ID171
KEGG Compound IDC00033
BioCyc IDACET
BiGG ID33590
Wikipedia LinkAcetic_acid
METLIN ID3206
PubChem Compound176
PDB IDNot Available
ChEBI ID15366
References
Synthesis ReferenceLaw, David John. Process for the preparation of carboxylic acids and/or derivatives thereof. PCT Int. Appl. (2007), 14pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
  4. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  5. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  6. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  7. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  8. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.