Record Information
Version2.0
Creation Date2012-05-31 13:52:23 -0600
Update Date2015-09-13 12:56:11 -0600
Secondary Accession Numbers
  • ECMDB01426
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 E. coli, 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
Weight:Average: 30.026
Monoisotopic: 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
DescriptionThis compound belongs to the class of organic compounds known as carbonyl compounds. These are organic compounds containing a carbonyl group, with the general structure RC(=O)R', where R=organyl, R'=H, N, O, organyl group or halide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCarbonyl compounds
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic 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:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Chloroalkane and chloroalkene degradation ec00625
  • Methane metabolism ec00680
  • Microbial metabolism in diverse environments ec01120
EcoCyc Pathways:
  • formaldehyde oxidation II (glutathione-dependent) PWY-1801
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-001i-9000000000-2863df3346e6e0796248View in MoNA
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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  • Castrillon DH, Sun D, Weremowicz S, Fisher RA, Crum CP, Genest DR: Discrimination of complete hydatidiform mole from its mimics by immunohistochemistry of the paternally imprinted gene product p57KIP2. Am J Surg Pathol. 2001 Oct;25(10):1225-30. Pubmed: 11688455
  • 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
  • Katsetos CD, Jami MM, Krishna L, Jackson R, Patchefsky AS, Cooper HS: Novel immunohistochemical localization of 28,000 molecular-weight (Mr) calcium binding protein (calbindin-D28k) in enterochromaffin cells of the human appendix and neuroendocrine tumors (carcinoids and small-cell carcinomas) of the midgut and foregut. Arch Pathol Lab Med. 1994 Jun;118(6):633-9. Pubmed: 8204010
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  • Lu CY, Chou AK, Wu CL, Yang CH, Chen JT, Wu PC, Lin SH, Muhammad R, Yang LC: Gene-gun particle with pro-opiomelanocortin cDNA produces analgesia against formalin-induced pain in rats. Gene Ther. 2002 Aug;9(15):1008-14. Pubmed: 12101431
  • 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
  • Shinkai M, Shinkai T, Puri P, Stringer MD: Elevated expression of IL2 is associated with increased infiltration of CD8+ T cells in biliary atresia. J Pediatr Surg. 2006 Feb;41(2):300-5. Pubmed: 16481239
  • Sriram S, Ljunggren-Rose A, Yao SY, Whetsell WO Jr: Detection of chlamydial bodies and antigens in the central nervous system of patients with multiple sclerosis. J Infect Dis. 2005 Oct 1;192(7):1219-28. Epub 2005 Sep 2. Pubmed: 16136465
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • van Dijk WR, van Haperen MJ, Stefanko SZ, van der Kamp AW: Monoclonal antibody selectively reactive with myelin sheaths of the peripheral nervous system in paraffin-embedded material. Acta Neuropathol (Berl). 1986;71(3-4):311-5. Pubmed: 2432751
  • Visee S, Soltner C, Rialland X, Machet MC, Loussouarn D, Milinkevitch S, Pasco-Papon A, Mercier P, Rousselet MC: Supratentorial primitive neuroectodermal tumours of the brain: multidirectional differentiation does not influence prognosis. A clinicopathological report of 18 patients. Histopathology. 2005 Apr;46(4):403-12. Pubmed: 15810952
  • Wilfredo Canchis P, Gonzalez SA, Isabel Fiel M, Chiriboga L, Yee H, Edlin BR, Jacobson IM, Talal AH: Hepatocyte proliferation in chronic hepatitis C: correlation with degree of liver disease and serum alpha-fetoprotein. Liver Int. 2004 Jun;24(3):198-203. Pubmed: 15189269
  • 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
  • Yang G, Ayala G, De Marzo A, Tian W, Frolov A, Wheeler TM, Thompson TC, Harper JW: Elevated Skp2 protein expression in human prostate cancer: association with loss of the cyclin-dependent kinase inhibitor p27 and PTEN and with reduced recurrence-free survival. Clin Cancer Res. 2002 Nov;8(11):3419-26. Pubmed: 12429629
  • Zeldin DC, Foley J, Boyle JE, Moomaw CR, Tomer KB, Parker C, Steenbergen C, Wu S: Predominant expression of an arachidonate epoxygenase in islets of Langerhans cells in human and rat pancreas. Endocrinology. 1997 Mar;138(3):1338-46. Pubmed: 9048644
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:
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 copper ion binding
Specific function:
The enzyme prefers aromatic over aliphatic amines
Gene Name:
tynA
Uniprot ID:
P46883
Molecular weight:
84378
Reactions
RCH(2)NH(2) + H(2)O + O(2) = RCHO + NH(3) + H(2)O(2).
2-phenylethylamine + H(2)O + O(2) = phenylacetaldehyde + NH(3) + H(2)O(2).
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
Uniprot ID:
P80644
Molecular weight:
21253
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
Uniprot ID:
P80645
Molecular weight:
41736
Reactions
An alkanesufonate (R-CH(2)-SO(3)H) + FMNH(2) + O(2) = an aldehyde (R-CHO) + FMN + sulfite + H(2)O.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative demethylation of N-methyl-L- tryptophan. Can also use other N-methyl amino acids, including sarcosine, which, however, is a poor substrate
Gene Name:
solA
Uniprot ID:
P40874
Molecular weight:
40902
Reactions
N-methyl-L-tryptophan + H(2)O + O(2) = L-tryptophan + formaldehyde + H(2)O(2).
General function:
Not Available
Specific function:
Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents). Dioxygenase that repairs alkylated DNA and RNA containing 3-methylcytosine or 1-methyladenine by oxidative demethylation. Has highest activity towards 3-methylcytosine. Has lower activity towards alkylated DNA containing ethenoadenine, and no detectable activity towards 1-methylguanine or 3-methylthymine. Accepts double-stranded and single-stranded substrates. Requires molecular oxygen, alpha-ketoglutarate and iron. Provides extensive resistance to alkylating agents such as MMS and DMS (SN2 agents), but not to MMNG and MNU (SN1 agents).
Gene Name:
alkB
Uniprot ID:
P05050
Molecular weight:
Not Available
Reactions
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).
DNA-base-CH(3) + 2-oxoglutarate + O(2) = DNA-base + formaldehyde + succinate + CO(2).

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