You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-19 21:23:05 UTC
HMDB IDHMDB0001426
Secondary Accession Numbers
  • HMDB01426
Metabolite Identification
Common NameFormaldehyde
DescriptionFormaldehyde is a highly reactive aldehyde gas formed by oxidation or incomplete combustion of hydrocarbons. In solution, it has a wide range of uses: in the manufacture of resins and textiles, as a disinfectant, and as a laboratory fixative or preservative. Formaldehyde solution (formalin) is considered a hazardous compound, and its vapor toxic. (From Reynolds, Martindale The Extra Pharmacopoeia, 30th ed, p717) -- Pubchem; The chemical compound formaldehyde (also known as methanal), is a gas with a pungent smell. It is the simplest aldehyde. Its chemical formula is H2CO. Formaldehyde was first synthesized by the Russian chemist Aleksandr Butlerov in 1859 but was conclusively identified by August Wilhelm van Hofmann in 1867. 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. Usually, these solutions contain a few percent methanol to limit the extent of polymerization. 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 the presence of basic catalysts, formaldehyde undergoes a Cannizaro reaction to produce formic acid and methanol. Because formaldehyde resins are used in many construction materials, including plywood, carpet, and spray-on insulating foams, and because these resins slowly give off formaldehyde over time, formaldehyde is one of the more common indoor air pollutants. At concentrations above 0.1 mg/kg in air, inhaled formaldehyde can irritate the eyes and mucous membranes, resulting in watery eyes, headache, a burning sensation in the throat, and difficulty breathing. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
FormaldehydChEBI
FORMALINChEBI
MethanalChEBI
Methylene oxideChEBI
OxomethaneChEBI
OxomethyleneChEBI
MethaldehydeHMDB
Methylene glycolHMDB
Aldeide formicaHMDB
FannoformHMDB
FormalinaHMDB
FormalineHMDB
FormalithHMDB
Formic aldehydeHMDB
FormolHMDB
ParaformHMDB
Chemical FormulaCH2O
Average Molecular Weight30.026
Monoisotopic Molecular Weight30.010564686
IUPAC Nameformaldehyde
Traditional Nameformaldehyde
CAS Registry Number50-00-0
SMILES
C=O
InChI Identifier
InChI=1S/CH2O/c1-2/h1H2
InChI KeyWSFSSNUMVMOOMR-UHFFFAOYSA-N
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Industrial process:

Naturally occurring process:

Role

Indirect biological role:

Environmental role:

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-92 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility400 mg/mL at 20 °CNot Available
LogP0.35HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility198 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity6.31 m³·mol⁻¹ChemAxon
Polarizability2.58 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-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 AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
  • Lysosome
  • Peroxisome
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Adipose Tissue
  • Adrenal Cortex
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Bone Marrow
  • Brain
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Lung
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Skin
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.3-19.3 uMAdult (>18 years old)BothNormal
    • Akadémiai Kiadó, ...
details
UrineDetected and Quantified0.2 (0.12-0.31) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03843
Phenol Explorer Compound IDNot Available
FoodDB IDFDB009445
KNApSAcK IDNot Available
Chemspider ID692
KEGG Compound IDC00067
BioCyc IDFORMALDEHYDE
BiGG ID33726
Wikipedia LinkFormaldehyde
METLIN ID3198
PubChem Compound712
PDB IDFOR
ChEBI ID16842
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Heck Hd, 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 ]
  7. 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 ]
  8. 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 ]
  9. 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. 1986;71(3-4):311-5. [PubMed:2432751 ]
  10. 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 ]
  11. Burke AP, Mont E, Kolodgie F, Virmani R: Thrombotic thrombocytopenic purpura causing rapid unexpected death: value of CD61 immunohistochemical staining in diagnosis. Cardiovasc Pathol. 2005 May-Jun;14(3):150-5. [PubMed:15914300 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. Koscielny J, Aslan T, Meyer O, Kiesewetter H, Jung F, Mrowietz C, Latza R: Use of the platelet reactivity index by Grotemeyer, platelet function analyzer, and retention test Homburg to monitor therapy with antiplatelet drugs. Semin Thromb Hemost. 2005;31(4):464-9. [PubMed:16149025 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]

Only showing the first 10 proteins. There are 41 proteins in total.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:
PIPOX
Uniprot ID:
Q9P0Z9
Molecular weight:
44065.515
Reactions
Sarcosine + Water + Oxygen → Glycine + Formaldehyde + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
DMGDH
Uniprot ID:
Q9UI17
Molecular weight:
96810.135
Reactions
Dimethylglycine + electron-transfer flavoprotein + Water → Sarcosine + Formaldehyde + reduced electron-transfer flavoproteindetails
Dimethylglycine + Electron-transferring flavoprotein + Water → Sarcosine + Formaldehyde + Reduced electron-transferring flavoproteindetails
General function:
Involved in peroxidase activity
Specific function:
May contribute to airway host defense against infection.
Gene Name:
LPO
Uniprot ID:
P22079
Molecular weight:
70983.6
General function:
Involved in antioxidant activity
Specific function:
Involved in redox regulation of the cell. Can reduce H(2)O(2) and short chain organic, fatty acid, and phospholipid hydroperoxides. May play a role in the regulation of phospholipid turnover as well as in protection against oxidative injury.
Gene Name:
PRDX6
Uniprot ID:
P30041
Molecular weight:
25034.715
Reactions
Methanol + Hydrogen peroxide → Formaldehyde + Waterdetails
General function:
Involved in peroxidase activity
Specific function:
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production of hypohalous acids, primarily hypochlorous acid in physiologic situations, and other toxic intermediates that greatly enhance PMN microbicidal activity.
Gene Name:
MPO
Uniprot ID:
P05164
Molecular weight:
83867.71
General function:
Involved in peroxidase activity
Specific function:
Mediates tyrosine nitration of secondary granule proteins in mature resting eosinophils. Shows significant inhibitory activity towards Mycobacterium tuberculosis H37Rv by inducing bacterial fragmentation and lysis.
Gene Name:
EPX
Uniprot ID:
P11678
Molecular weight:
81039.5
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in copper ion binding
Specific function:
Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:
AOC2
Uniprot ID:
O75106
Molecular weight:
80515.11
Reactions
Methylamine + Oxygen + Water → Formaldehyde + Ammonia + Hydrogen peroxidedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
SARDH
Uniprot ID:
Q9UL12
Molecular weight:
101035.985
Reactions
Sarcosine + Water + electron-transfer flavoprotein → Glycine + Formaldehyde + reduced electron-transfer flavoproteindetails
Sarcosine + Electron-transferring flavoprotein + Water → Glycine + Formaldehyde + Reduced electron-transferring flavoproteindetails
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585

Only showing the first 10 proteins. There are 41 proteins in total.