Record Information
Version2.0
Creation Date2012-05-31 13:54:48 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01875
Identification
Name:Methanol
DescriptionMethanol is the simplest alcohol, and is a light, volatile, colourless, flammable, poisonous liquid with a distinctive odor that is somewhat milder and sweeter than ethanol. It is produced naturally in the anaerobic metabolism of many varieties of bacteria, and is ubiquitous in the environment. As a result, there is a small fraction of methanol vapor in the atmosphere. (Wikipedia).
Structure
Thumb
Synonyms:
  • Alcool methylique
  • Alcool metilico
  • Carbinol
  • CH3OH
  • Colonial spirit
  • Columbian spirit
  • Columbian spirits
  • Hydroxymethane
  • MeOH
  • Metanolo
  • Methanol
  • Methanol-water mixture
  • Methyl alcohol
  • Methyl hydroxide
  • Methylalkohol
  • Methylol
  • MetOH
  • Metylowy alkohol
  • Monohydroxymethane
  • Pyro alcohol
  • Pyroxylic spirit
  • Spirit of wood
  • Wood alcohol
  • Wood naphtha
  • Wood spirit
Chemical Formula:CH4O
Weight:Average: 32.0419
Monoisotopic: 32.02621475
InChI Key:OKKJLVBELUTLKV-UHFFFAOYSA-N
InChI:InChI=1S/CH4O/c1-2/h2H,1H3
CAS number:67-56-1
IUPAC Name:methanol
Traditional IUPAC Name:methanol
SMILES:CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Liquid
Charge:0
Melting point:-97.6 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000 mg/mL at 25 oC [RIDDICK,JA et al. (1986)]PhysProp
LogP:-0.77 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility519 g/LALOGPS
logP-1.4ALOGPS
logP-0.52ChemAxon
logS1.21ALOGPS
pKa (Strongest Acidic)15.78ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.26 m³·mol⁻¹ChemAxon
Polarizability3.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Biotin metabolismPW000762 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • 7-keto-8-aminopelargonate biosynthesis I PWY-6519
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-2173f5595be586c5c940View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-14ea8d185227ede9bff7View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-2173f5595be586c5c940View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001i-9000000000-14ea8d185227ede9bff7View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9000000000-4c6569479bda044bbec6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dr-9000000000-7cc6047a4db3644c3b83View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0000-0000000000-e3b0c44298fc1c149afbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-6d633534165eedf07b4dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9000000000-757b6964771196ee308fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001i-9000000000-fef92d3f671a9282b5a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-60e278e17032d30c1c8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-9d3a102faa7d9058eb88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-9d3a102faa7d9058eb88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-9d3a102faa7d9058eb88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-8071a59ff1eb417f4a9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000000000-8071a59ff1eb417f4a9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-8071a59ff1eb417f4a9aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-5a9d4ce5dca0ae1a6765View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Avella J, Briglia E, Harleman G, Lehrer M: Percutaneous absorption and distribution of methanol in a homicide. J Anal Toxicol. 2005 Oct;29(7):734-7. Pubmed: 16419410
  • Batterman SA, Franzblau A, Zhou N: Airborne emissions at skin surfaces: a potential biological exposure index. Int Arch Occup Environ Health. 1996;68(4):268-74. Pubmed: 8738358
  • Bogdanov-Berezovsky A, Glesinger R, Kachko L, Arbel E, Rosenberg L, Grossman N: Accreditation of skin from a methanol-poisoned victim for banking and grafting. Transplantation. 2002 Jun 27;73(12):1913-7. Pubmed: 12131687
  • Comoglu S, Ozen B, Ozbakir S: Methanol intoxication with bilateral basal ganglia infarct. Australas Radiol. 2001 Aug;45(3):357-8. Pubmed: 11531765
  • Ferrari LA, Arado MG, Nardo CA, Giannuzzi L: Post-mortem analysis of formic acid disposition in acute methanol intoxication. Forensic Sci Int. 2003 Apr 23;133(1-2):152-8. Pubmed: 12742704
  • Heinig K, Henion J: Determination of carnitine and acylcarnitines in biological samples by capillary electrophoresis-mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Dec 10;735(2):171-88. Pubmed: 10670733
  • Jose N, Ajith TA, Janardhanan KK: Methanol extract of the oyster mushroom, Pleurotus florida, inhibits inflammation and platelet aggregation. Phytother Res. 2004 Jan;18(1):43-6. Pubmed: 14750200
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kaphalia BS, Carr JB, Ansari GA: Increased endobiotic fatty acid methyl esters following exposure to methanol. Fundam Appl Toxicol. 1995 Dec;28(2):264-73. Pubmed: 8835236
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Keum YS, Park KK, Lee JM, Chun KS, Park JH, Lee SK, Kwon H, Surh YJ: Antioxidant and anti-tumor promoting activities of the methanol extract of heat-processed ginseng. Cancer Lett. 2000 Mar 13;150(1):41-8. Pubmed: 10755385
  • Lee XP, Kumazawa T, Kondo K, Sato K, Suzuki O: Analysis of methanol or formic acid in body fluids by headspace solid-phase microextraction and capillary gas chromatography. J Chromatogr B Biomed Sci Appl. 1999 Oct 29;734(1):155-62. Pubmed: 10574201
  • Megarbane B, Borron SW, Baud FJ: Current recommendations for treatment of severe toxic alcohol poisonings. Intensive Care Med. 2005 Feb;31(2):189-95. Epub 2004 Dec 31. Pubmed: 15627163
  • Nagasawa H, Wada M, Koyama S, Kawanami T, Kurita K, Kato T: [A case of methanol intoxication with optic neuropathy visualized on STIR sequence of MR images] Rinsho Shinkeigaku. 2005 Jul;45(7):527-30. Pubmed: 16119839
  • Purssell RA, Lynd LD, Koga Y: The use of the osmole gap as a screening test for the presence of exogenous substances. Toxicol Rev. 2004;23(3):189-202. Pubmed: 15862085
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Vassiliadis J, Graudins A, Dowsett RP: Triethylene glycol poisoning treated with intravenous ethanol infusion. J Toxicol Clin Toxicol. 1999;37(6):773-6. Pubmed: 10584590
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Yu C, Shin YG, Chow A, Li Y, Kosmeder JW, Lee YS, Hirschelman WH, Pezzuto JM, Mehta RG, van Breemen RB: Human, rat, and mouse metabolism of resveratrol. Pharm Res. 2002 Dec;19(12):1907-14. Pubmed: 12523673
Synthesis Reference:Cummings, Donald Ray. Process for production of methanol from a methane gas stream. PCT Int. Appl. (2007), 21pp.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17790
HMDB IDHMDB01875
Pubchem Compound ID887
Kegg IDC00132
ChemSpider ID864
WikipediaMethanol
BioCyc IDMETOH
EcoCyc IDMETOH
Ligand ExpoOME

Enzymes

General function:
Involved in two-component response regulator activity
Specific function:
Involved in the modulation of the chemotaxis system; catalyzes the demethylation of specific methylglutamate residues introduced into the chemoreceptors (methyl-accepting chemotaxis proteins) by CheR
Gene Name:
cheB
Uniprot ID:
P07330
Molecular weight:
37467
Reactions
Protein L-glutamate O(5)-methyl ester + H(2)O = protein L-glutamate + methanol.
General function:
Involved in biotin biosynthetic process
Specific function:
Shows carboxylesterase activity with a preference for short chain fatty acid esters (acyl chain length of up to 6 carbons). Also displays a weak thioesterase activity. Can form a complex with CoA, and may be involved in the condensation of CoA and pimelic acid into pimeloyl-CoA, a precursor in biotin biosynthesis
Gene Name:
bioH
Uniprot ID:
P13001
Molecular weight:
28505
Reactions
Pimelyl-[acyl-carrier protein] methyl ester + H(2)O = pimelyl-[acyl-carrier protein] + methanol.
General function:
Involved in catalase activity
Specific function:
Bifunctional enzyme with both catalase and broad- spectrum peroxidase activity. Displays also NADH oxidase, INH lyase and isonicotinoyl-NAD synthase activity
Gene Name:
katG
Uniprot ID:
P13029
Molecular weight:
80023
Reactions
Donor + H(2)O(2) = oxidized donor + 2 H(2)O.
2 H(2)O(2) = O(2) + 2 H(2)O.
General function:
Involved in catalase activity
Specific function:
Decomposes hydrogen peroxide into water and oxygen; serves to protect cells from the toxic effects of hydrogen peroxide
Gene Name:
katE
Uniprot ID:
P21179
Molecular weight:
84162
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.
General function:
Involved in pectinesterase activity
Specific function:
Putative thioesterase. Does not bind pectin, and has no pectinesterase activity
Gene Name:
ybhC
Uniprot ID:
P46130
Molecular weight:
46082
General function:
Not Available
Specific function:
Not Available
Gene Name:
aes
Uniprot ID:
P23872
Molecular weight:
Not Available

Transporters

General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368