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
Description:Methanol 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
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These 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 Solubility519.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.26 m3·mol-1ChemAxon
Polarizability3.38 Å3ChemAxon
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 Pw000762Pw000762 greyscalePw000762 simple
Starch and sucrose metabolismPW000941 Pw000941Pw000941 greyscalePw000941 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 - GC-MSsplash10-001i-9000000000-4c6569479bda044bbec6View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-2173f5595be586c5c940View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-001i-9000000000-14ea8d185227ede9bff7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00dr-9000000000-7cc6047a4db3644c3b83View in MoNA
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
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-5a9d4ce5dca0ae1a6765View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
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