Basic Info

Common NameFormaldehyde(F03453)
2D Structure
Description

Formaldehyde 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.

FRCD IDF03453
CAS Number50-00-0
PubChem CID712
FormulaCH2O
IUPAC Name

formaldehyde

InChI Key

WSFSSNUMVMOOMR-UHFFFAOYSA-N

InChI

InChI=1S/CH2O/c1-2/h1H2

Canonical SMILES

C=O

Isomeric SMILES

C=O

WikipediaFormaldehyde
Synonyms
        
            Paraform
        
            formaldehyde
        
            formalin
        
            methanal
        
            formol
        
            Methylene oxide
        
            Paraformaldehyde
        
            Oxomethane
        
            50-00-0
        
            Formic aldehyde
        
Classifies
                

                  
                    Illegal Additives
                  
                    Pollutant
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds
SubclassCarbonyl compounds
Intermediate Tree NodesNot available
Direct ParentCarbonyl compounds
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsOrganic oxide - Hydrocarbon derivative - Carbonyl group - Aliphatic acyclic compound
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.

Properties

Property NameProperty Value
Molecular Weight30.026
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Complexity2
Monoisotopic Mass30.011
Exact Mass30.011
XLogP1.2
Formal Charge0
Heavy Atom Count2
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9820
Human Intestinal AbsorptionHIA+0.9757
Caco-2 PermeabilityCaco2+0.7834
P-glycoprotein SubstrateNon-substrate0.8663
P-glycoprotein InhibitorNon-inhibitor0.9633
Non-inhibitor0.9831
Renal Organic Cation TransporterNon-inhibitor0.9145
Distribution
Subcellular localizationMitochondria0.4617
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8628
CYP450 2D6 SubstrateNon-substrate0.9157
CYP450 3A4 SubstrateNon-substrate0.8203
CYP450 1A2 InhibitorNon-inhibitor0.8503
CYP450 2C9 InhibitorNon-inhibitor0.9662
CYP450 2D6 InhibitorNon-inhibitor0.9735
CYP450 2C19 InhibitorNon-inhibitor0.9531
CYP450 3A4 InhibitorNon-inhibitor0.9770
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9443
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9573
Non-inhibitor0.9823
AMES ToxicityAMES toxic0.6450
CarcinogensCarcinogens 0.6567
Fish ToxicityHigh FHMT0.7216
Tetrahymena Pyriformis ToxicityHigh TPT0.8773
Honey Bee ToxicityHigh HBT0.8071
BiodegradationReady biodegradable0.7562
Acute Oral ToxicityII0.7606
Carcinogenicity (Three-class)Non-required0.7138

Model Value Unit
Absorption
Aqueous solubility0.6503LogS
Caco-2 Permeability1.6527LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5082LD50, mol/kg
Fish Toxicity0.3638pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6879pIGC50, ug/L

References

TitleJournalDatePubmed ID
Immunogenicity of a Bivalent Non-Purified Recombinant Vaccine against Botulism in Cattle.Toxins (Basel)2018 Sep 2030241350
Combination of probiotic yeast and lactic acid bacteria as starter culture toproduce maize-based beverages.Food Res Int2018 Sep30007675
Ultrafast and Efficient Detection of Formaldehyde in Aqueous Solutions Using Chitosan-based Fluorescent Polymers.ACS Sens2018 Oct 2230346151
Method for preclinical pathology evaluation and analysis of cardiovascularimplantable electronic device implant sites.Cardiovasc Pathol2018 May 1830014985
The interaction between bacterial abundance and selected pollutants concentrationlevels in an arctic catchment (southwest Spitsbergen, Svalbard).Sci Total Environ2018 May 129227942
Comparison of fresh watermelon juice aroma characteristics of five varietiesbased on gas chromatography-olfactometry-mass spectrometry.Food Res Int2018 May29580469
Volatile Compounds Related to 'Stone Fruit' Aroma Attributes in Viognier andChardonnay Wines.J Agric Food Chem2018 Mar 2129485286
Investigation on Key Molecules of Huanglongbing (HLB)-Induced Orange JuiceOff-flavor.J Agric Food Chem2018 Mar 1428285516
Particulate matter emissions and gaseous air toxic pollutants from commercial meat cooking operations.J Environ Sci (China)2018 Mar29548387
Effect of Fermentation Processing on the Flavor of Baijiu.J Agric Food Chem2018 Jun 629751730
Dynamic microbial succession of Shanxi aged vinegar and its correlation withflavor metabolites during different stages of acetic acid fermentation.Sci Rep2018 Jun 529872163
Superchilled storage (-2.5 ± 1°C) extends the retention of taste-active andvolatile compounds of yellow-feather chicken soup.Anim Sci J2018 Jun29665200
STP Position Paper: Recommended Best Practices for Sampling, Processing, andAnalysis of the Peripheral Nervous System (Nerves and Somatic and AutonomicGanglia) during Nonclinical Toxicity Studies.Toxicol Pathol2018 Jun29787347
Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia OrangeJuices Not from Concentrate (NFC) during Chilled Storage.J Agric Food Chem2018 Jul 1829889522
ddPCR applied on archived Continuous Plankton Recorder samples reveals long-term occurrence of class 1 integrons and a sulphonamide resistance gene in marineplankton communities.Environ Microbiol Rep2018 Jul 1830022610
Effect of Temperature on Flavor Compounds and Sensory Characteristics of MaillardReaction Products Derived from Mushroom Hydrolysate.Molecules2018 Jan 2629373560
Mechanisms and kinetics of heme iron nitrosylation in an in vitrogastro-intestinal model.Food Chem2018 Jan 1528873645
Magnetic mesoporous thiourea-formaldehyde resin as selective adsorbent: A simple and highly-sensitive electroanalysis strategy for lead ions in drinking water andmilk by solid state-based anodic stripping.Food Chem2018 Jan 1528873584
Identifying principles for effective messages about chemicals in cigarette smoke.Prev Med2018 Jan28890353
Abundance of DNA adducts of 4-oxo-2-alkenals, lipid peroxidation-derived highlyreactive genotoxins.J Clin Biochem Nutr2018 Jan29362517

Targets

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 ]