Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000382
Identification
Name: Formaldehyde
Description:Formaldehyde is a highly reactive aldehyde gas. It is the simplest aldehyde. Its chemical formula is H2CO. Although formaldehyde is a gas at room temperature, it is readily soluble in water, and it is most commonly sold as a 37% solution in water called by trade names such as formalin or formol. In water, formaldehyde polymerizes, and formalin actually contains very little formaldehyde in the form of H2CO monomer. Formaldehyde exhibits most of the general chemical properties of the aldehydes, except that is generally more reactive than other aldehydes. Formaldehyde is a potent electrophile. It can participate in electrophilic aromatic substitution reactions with aromatic compounds and can undergo electrophilic addition reactions with alkenes. In Pseudomonas aeruginosa, formaldehyde is formed by the breakdown of N-methyltryptophan and FMNH by their corresponding oxidases.
Structure
Thumb
Synonyms:
  • Aldeide formica
  • Chlodithan
  • Chlodithane
  • Fannoform
  • Formaldehyde
  • Formalin
  • Formalina
  • Formaline
  • Formalith
  • Formic aldehyde
  • Formol
  • Methaldehyde
  • Methanal
  • Methylene glycol
  • Methylene oxide
  • Oxomethylene
  • Paraform
Chemical Formula: CH2O
Average Molecular Weight: 30.026
Monoisotopic Molecular Weight: 30.010564686
InChI Key: WSFSSNUMVMOOMR-UHFFFAOYSA-N
InChI:InChI=1S/CH2O/c1-2/h1H2
CAS number: 50-00-0
IUPAC Name:formaldehyde
Traditional IUPAC Name: formaldehyde
SMILES:C=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as hydrocarbon derivatives. These are derivatives of hydrocarbons obtained by substituting one or more carbon atoms by an heteroatom. THey contain at least one carbon atom and heteroatom.
Kingdom Organic compounds
Super ClassHydrocarbon derivatives
Class Not Available
Sub ClassNot Available
Direct Parent Hydrocarbon derivatives
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aldehyde
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Liquid
Charge:0
Melting point: -92 °C
Experimental Properties:
PropertyValueSource
Water Solubility:400 mg/mL at 20 oC [PICKRELL,JA et al. (1983)]PhysProp
LogP:0.35 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility198.0 mg/mLALOGPS
logP-0.68ALOGPS
logP-0.47ChemAxon
logS0.82ALOGPS
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity6.31 m3·mol-1ChemAxon
Polarizability2.58 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9000000000-793a330f9e6c7661e86dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-9000000000-5ea4ad4bdb0565b737bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-5ea4ad4bdb0565b737bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5ea4ad4bdb0565b737bbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-004i-9000000000-58b4df664ee160d1f943View 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
References
References:
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  • Heck H, Casanova M: The implausibility of leukemia induction by formaldehyde: a critical review of the biological evidence on distant-site toxicity. Regul Toxicol Pharmacol. 2004 Oct;40(2):92-106. Pubmed: 15450713
  • 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
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  • Marinkovic S, Gibo H, Zelic O, Nikodijevic I: The neurovascular relationships and the blood supply of the trochlear nerve: surgical anatomy of its cisternal segment. Neurosurgery. 1996 Jan;38(1):161-9. Pubmed: 8747965
  • Moore GR, Leung E, MacKay AL, Vavasour IM, Whittall KP, Cover KS, Li DK, Hashimoto SA, Oger J, Sprinkle TJ, Paty DW: A pathology-MRI study of the short-T2 component in formalin-fixed multiple sclerosis brain. Neurology. 2000 Nov 28;55(10):1506-10. Pubmed: 11094105
  • Nader N, Raverot G, Emptoz-Bonneton A, Dechaud H, Bonnay M, Baudin E, Pugeat M: Mitotane has an estrogenic effect on sex hormone-binding globulin and corticosteroid-binding globulin in humans. J Clin Endocrinol Metab. 2006 Jun;91(6):2165-70. Epub 2006 Mar 21. Pubmed: 16551731
  • North WG, Memoli VA, Keegan BP: Immunohistochemical detection of NRSA on small cell lung cancer with a monoclonal antibody (MAG-1) that recognizes the carboxyl terminus of provasopressin. Appl Immunohistochem Mol Morphol. 2005 Dec;13(4):363-6. Pubmed: 16280667
  • Pagani S, Mirtella D, Mencarelli R, Rodriguez D, Cingolani M: Postmortem distribution of sildenafil in histological material. J Anal Toxicol. 2005 May-Jun;29(4):254-7. Pubmed: 15975255
  • Panasiuk A, Prokopowicz D, Dzieciol J: p53 protein expression in chronic hepatitis C; effect of interferon alpha 2b therapy. Hepatogastroenterology. 2005 Jul-Aug;52(64):1176-9. Pubmed: 16001656
  • Shakleya DM, Kraner JC, Kaplan JA, Gannett PM, Callery PS: Identification of N,N-dimethylamphetamine formed by methylation of methamphetamine in formalin-fixed liver tissue by multistage mass spectrometry. Forensic Sci Int. 2006 Mar 10;157(2-3):87-92. Pubmed: 15893897
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Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID16842
HMDB IDHMDB01426
Pubchem Compound ID712
Kegg IDC00067
ChemSpider ID692
WikipediaFormaldehyde
BioCyc IDFORMALDEHYDE
EcoCyc IDFORMALDEHYDE
Ligand ExpoFOR

Enzymes

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
Locus Tag:
PA2147
Molecular weight:
78 kDa
Reactions
2 H(2)O(2) = O(2) + 2 H(2)O.
General function:
Involved in FMN reductase activity
Specific function:
Catalyzes an NAD(P)H-dependent reduction of FMN, but is also able to reduce FAD or riboflavin
Gene Name:
ssuE
Locus Tag:
PA3446
Molecular weight:
21.5 kDa
Reactions
FMNH(2) + NADP(+) = FMN + NADPH.
General function:
Involved in alkanesulfonate monooxygenase activity
Specific function:
Involved in desulfonation of aliphatic sulfonates. Catalyzes the conversion of pentanesulfonic acid to sulfite and pentaldehyde and is able to desulfonate a wide range of sulfonated substrates including C-2 to C-10 unsubstituted linear alkanesulfonates, substituted ethanesulfonic acids and sulfonated buffers
Gene Name:
ssuD
Locus Tag:
PA3444
Molecular weight:
41.6 kDa
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.

Transporters