Tmic
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Record Information
Version2.0
Creation Date2009-03-06 18:58:21 UTC
Update Date2014-12-24 20:21:24 UTC
Accession NumberT3D0244
Identification
Common NameFormaldehyde
ClassSmall Molecule
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.
Compound Type
  • Aldehyde
  • Cigarette Toxin
  • Cosmetic Toxin
  • Disinfectant
  • Fixative
  • Food Toxin
  • Household Toxin
  • Industrial Precursor/Intermediate
  • Industrial/Workplace Toxin
  • Lachrymator
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Pollutant
Chemical Structure
Thumb
Synonyms
Synonym
Fannoform
Formalin
Formalina
Formaline
Formalith
Formic aldehyde
Formol
Methaldehyde
Methanal
Methyl aldehyde
Methylene glycol
Methylene oxide
Oxomethane
Oxomethylene
Oxymethylene
Paraform
Paraformaldehyde
Chemical FormulaCH2O
Average Molecular Mass30.026 g/mol
Monoisotopic Mass30.011 g/mol
CAS Registry Number50-00-0
IUPAC Nameformaldehyde
Traditional Nameformaldehyde
SMILESC=O
InChI IdentifierInChI=1S/CH2O/c1-2/h1H2
InChI KeyInChIKey=WSFSSNUMVMOOMR-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Lysosome
  • Mitochondria
  • Peroxisome
Biofluid LocationsNot Available
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
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Applications
Biological Roles
Chemical Roles
Physical Properties
StateLiquid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point-92°C
Boiling PointNot Available
Solubility400 mg/mL at 20°C [PICKRELL,JA et al. (1983)]
LogP0.35
Predicted Properties
PropertyValueSource
Water Solubility198 g/LALOGPS
logP-0.68ALOGPS
logP-0.47ChemAxon
logS0.82ALOGPS
pKa (Strongest Basic)-8.1ChemAxon
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
Toxicity Profile
Route of ExposureOral (26) ; inhalation (26) ; dermal (26)
Mechanism of ToxicityIt is likely that formaldehyde toxicity occurs when intracellular levels saturate formaldehyde dehydrogenase activity, allowing the unmetabolized intact molecule to exert its effects. Formaldehyde is known to form cross links between protein and DNA and undergo metabolic incorporation into macromolecules (DNA, RNA, and proteins). (26)
MetabolismFormaldehyde may be absorbed following inhalation, oral, or dermal exposure. It is an essential metabolic intermediate in all cells and is produced during the normal metabolism of serine, glycine, methionine, and choline and also by the demethylation of N-, S-, and O-methyl compounds. Exogenous formaldehyde is metabolized to formate by the enzyme formaldehyde dehydrogenase at the initial site of contact. After oxidation of formaldehyde to formate, the carbon atom is further oxidized to carbon dioxide or incorporated into purines, thymidine, and amino acids via tetrahydrofolatedependent one-carbon biosynthetic pathways. Formaldehyde is not stored in the body and is excreted in the urine (primarily as formic acid), incorporated into other cellular molecules, or exhaled as carbon dioxide. (26)
Toxicity ValuesLD50: 300 mg/kg (Subcutaneous, Mouse) (22) LD50: 42 mg/kg (Oral, Mouse) (22) LD50: 87 mg/kg (Intravenous, Rat) (22) LD50: 16 mg/kg (Intraperitoneal, Mouse) (23) LC50: 0.414 mg/L over 4 hours (Inhalation, Mouse) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (25)
Uses/SourcesFormaldehyde is used in the production of fertilizer, paper, plywood, and urea-formaldehyde resins. It is also also used as a preservative in some foods and in many products used around the house, such as antiseptics, medicines, and cosmetics. (26)
Minimum Risk LevelAcute Inhalation: 0.04 ppm (24) Intermediate Inhalation: 0.03 ppm (24) Chronic Inhalation: 0.008 ppm (24) Intermediate Oral: 0.3 mg/kg/day (24) Chronic Oral: 0.2 mg/kg/day (24)
Health EffectsDrinking large amounts of formaldehyde can cause severe pain, vomiting, coma, and possible death. Formaldehyde is also a known human carcinogen. (26)
SymptomsLow levels of formaldehyde can cause irritation of the eyes, nose, throat, and skin. (26)
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03843
HMDB IDHMDB01426
PubChem Compound ID712
ChEMBL IDCHEMBL1255
ChemSpider ID692
KEGG IDC00067
UniProt IDNot Available
OMIM ID
ChEBI ID16842
BioCyc IDFORMALDEHYDE
CTD IDD005557
Stitch IDFormaldehyde
PDB IDFOR
ACToR ID647
Wikipedia LinkFormaldehyde
References
Synthesis Reference

Walter Hasselman, Jr., “Process for the preparation of phenol-urea-formaldehyde condensation products.” U.S. Patent US4345061, issued August, 1926.

MSDSLink
General References
  1. Seifert J, Pewnim T: Alteration of mice L-tryptophan metabolism by the organophosphorous acid triester diazinon. Biochem Pharmacol. 1992 Dec 1;44(11):2243-50. [1282004 ]
  2. 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. [12101431 ]
  3. 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. [12429629 ]
  4. 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. [11688455 ]
  5. 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. [8747965 ]
  6. 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. [15975255 ]
  7. 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. [15450713 ]
  8. 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. [16481239 ]
  9. 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. [16001656 ]
  10. 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. [2432751 ]
  11. 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. [15893897 ]
  12. 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. [15914300 ]
  13. 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. [15810952 ]
  14. 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. [16136465 ]
  15. 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. [15189269 ]
  16. 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. [9048644 ]
  17. 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. [11094105 ]
  18. 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. [16149025 ]
  19. 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. [16551731 ]
  20. 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. [16280667 ]
  21. 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. [8204010 ]
  22. Lewis RJ Sr. (ed) (2004). Sax's Dangerous Properties of Industrial Materials. 11th Edition. Hoboken, NJ: Wiley-Interscience, Wiley & Sons, Inc.
  23. Bingham, E, Cohrssen, B, and Powell, CH (2001). Patty's Toxicology Volumes 1-9. 5th ed. New York, N.Y: John Wiley & Sons.
  24. ATSDR - Agency for Toxic Substances and Disease Registry (2001). Minimal Risk Levels (MRLs) for Hazardous Substances. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
  25. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  26. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
2. RNA
References
  1. ATSDR - Agency for Toxic Substances and Disease Registry (1999). Toxicological profile for formaldehyde. U.S. Public Health Service in collaboration with U.S. Environmental Protection Agency (EPA). [Link]
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]