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Formic acid (FDB012804)

Record Information
Version1.0
Creation date2010-04-08 22:10:22 UTC
Update date2020-09-17 15:35:10 UTC
Primary IDFDB012804
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFormic acid
DescriptionFormic acid, also known as methanoic acid, is the simplest carboxylic acid, and has the chemical formula HCOOH. It is an important intermediate in chemical synthesis and occurs naturally, most notably in some ants. Esters, salts, and the anion derived from formic acid are called formates. Industrially, formic acid is produced through the oxidation of methanol. Formate is an intermediate in normal metabolism. It takes part in the metabolism of one-carbon compounds and its carbon may appear in methyl groups undergoing transmethylation. It is eventually oxidized to carbon dioxide. Formate is typically produced as a by-product in the production of acetate. It is responsible for both metabolic acidosis and disrupting mitochondrial electron transport and energy production by inhibiting cytochrome oxidase activity, the terminal electron acceptor of the electron transport chain. Cell death from cytochrome oxidase inhibition by formate is believed to result partly from depletion of ATP, reducing energy concentrations so that essential cell functions cannot be maintained. Furthermore, inhibition of cytochrome oxidase by formate may also cause cell death by increased production of cytotoxic reactive oxygen species (ROS) secondary to the blockade of the electron transport chain. In nature, formic acid is found in the stings and bites of many insects of the order Hymenoptera, including bees and ants. The principal use of formic acid is as a preservative and antibacterial agent in livestock feed. When sprayed on fresh hay or other silage, it arrests certain decay processes and causes the feed to retain its nutritive value longer. Urinary formate is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis, Streptococcus group B, Staphylococcus saprophyticus (PMID: 22292465).
CAS Number64-18-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility477 g/LALOGPS
logP-0.47ALOGPS
logP-0.27ChemAxon
logS1.02ALOGPS
pKa (Strongest Acidic)4.27ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity8.15 m³·mol⁻¹ChemAxon
Polarizability3.37 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaCH2O2
IUPAC nameformic acid
InChI IdentifierInChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
Isomeric SMILESOC=O
Average Molecular Weight46.0254
Monoisotopic Molecular Weight46.005479308
Classification
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 26.10%; H 4.38%; O 69.52%DFC
Melting PointMp 8.4°DFC
Boiling PointBp120 50°DFC
Experimental Water Solubility1000 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP-0.54HANSCH,C ET AL. (1995)
Experimental pKa3.744
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd204 1.22DFC
Refractive Indexn20D 1.3714DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-004j-9000000000-2e63b0c1e2e417b0d7472015-03-01View Spectrum
Predicted GC-MSFormic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9000000000-5d27bb312e37a2c8994fSpectrum
Predicted GC-MSFormic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-9200000000-2a89ba98485194acd75aSpectrum
Predicted GC-MSFormic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSFormic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0002-9000000000-a8fbddf8ca4197b300132020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-0002-9000000000-98310116f8a2d6a969ce2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-0002-9000000000-ec8753fd9790a3cf0be82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0002-9000000000-121d1a025b72a70e412a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0002-9000000000-5f1955dee7ab988e86dd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0002-9000000000-f8e14272296ee06d19f42020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff72015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-d948d5d95ae14e701f572021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-d948d5d95ae14e701f572021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-d948d5d95ae14e701f572021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-92190863fc6ae28a87892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-92190863fc6ae28a87892021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-348f481062f48991a0aa2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID278
ChEMBL IDCHEMBL116736
KEGG Compound IDC00058
Pubchem Compound ID284
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01942
HMDB IDHMDB00142
CRC / DFC (Dictionary of Food Compounds) IDHLG71-V:HLG71-V
EAFUS ID1398
Dr. Duke IDFORMIC-ACID
BIGG ID33693
KNApSAcK IDC00001182
HET IDFMT
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1008401
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acaricide22153 A substance used to destroy pests of the subclass Acari (mites and ticks).DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti syncopicDUKE
astringent74783 A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.DUKE
corrosiveDUKE
counterirritantDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungistatDUKE
fungitoxic24127 A substance used to destroy fungal pests.DUKE
irritantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
preservative65255 Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes.DUKE
toxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.CHEBI
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
S-formylglutathione hydrolaseESDP10768
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenaseADI1Q9BV57
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Peptide deformylase, mitochondrialPDFQ9HBH1
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1LQ6UB35
Methylenetetrahydrofolate dehydrogenase (NADP+ dependent) 2, methenyltetrahydrofolate cyclohydrolaseMTHFD2Q7Z650
Pathways
NameSMPDB LinkKEGG Link
Folate MetabolismSMP00053 map00670
Pterine BiosynthesisSMP00005 map00790
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
pungent
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vinegar
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
formyl
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).