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Record Information
Version1.0
Creation Date2016-05-19 01:31:22 UTC
Update Date2016-10-28 10:00:56 UTC
Accession NumberCHEM003983
Identification
Common NameFormic acid
ClassSmall Molecule
DescriptionFormic acid (systematically called methanoic acid) is the simplest carboxylic acid. It is an important intermediate in chemical synthesis and occurs naturally, most famously in the venom of bee and ant stings. It is commonly used as a preservative and antibacterial agent in livestock feed.
Contaminant Sources
  • Clean Air Act Chemicals
  • DEA Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • Tobacco Smoke Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
Acide formiqueChEBI
AmeisensaeureChEBI
Aminic acidChEBI
BilorinChEBI
Formylic acidChEBI
H-COOHChEBI
HCO2HChEBI
HCOOHChEBI
Hydrogen carboxylic acidChEBI
Methanoic acidChEBI
Methoic acidChEBI
AminateGenerator
FormylateGenerator
Hydrogen carboxylateGenerator
MethanoateGenerator
MethoateGenerator
FormateGenerator
Add-FHMDB
AmeisensaureHMDB
Collo-bueglattHMDB
Collo-didaxHMDB
FormiraHMDB
FormisotonHMDB
Methanoic acid monomerHMDB
MyrmicylHMDB
Sodium formateHMDB
SybestHMDB
Wonderbond hardener m 600lHMDB
Calcium formateHMDB
Cobalt(II) formate dihydrateHMDB
Formic acid, aluminum saltHMDB
Formic acid, copper saltHMDB
Formic acid, cromium (+3) saltHMDB
Lithium formateHMDB
Ammonium formateHMDB
Formic acid, ammonium (4:1) saltHMDB
Formic acid, ammonium saltHMDB
Formic acid, calcium saltHMDB
Formic acid, copper (+2) saltHMDB
Formic acid, lead (+2) saltHMDB
Formic acid, lead saltHMDB
Formic acid, nickel saltHMDB
Formic acid, potassium saltHMDB
Formic acid, strontium saltHMDB
MafusolHMDB
Ammonium tetraformateHMDB
Formic acid, 14C-labeledHMDB
Formic acid, cobalt (+2) saltHMDB
Formic acid, copper, ammonium saltHMDB
Formic acid, sodium saltHMDB
Formic acid, sodium salt, 14C-labeledHMDB
Formic acid, ammonium (2:1) saltHMDB
Formic acid, cadmium saltHMDB
Formic acid, cesium saltHMDB
Formic acid, copper, nickel saltHMDB
Formic acid, cromium (+3), sodium (4:1:1) saltHMDB
Formic acid, lithium saltHMDB
Formic acid, magnesium saltHMDB
Formic acid, nickel (+2) saltHMDB
Formic acid, rubidium saltHMDB
Formic acid, sodium salt, 13C-labeledHMDB
Formic acid, thallium (+1) saltHMDB
Formic acid, zinc saltHMDB
Nickel formate dihydrateHMDB
Aluminum formateHMDB
Potassium formateHMDB
Strontium formateHMDB
Lead formateHMDB
Nickel formateHMDB
Chromic formateHMDB
Cobaltous formateHMDB
Cupric formateHMDB
Magnesium formateHMDB
Zinc formateHMDB
Chemical FormulaCH2O2
Average Molecular Mass46.025 g/mol
Monoisotopic Mass46.005 g/mol
CAS Registry Number64-18-6
IUPAC Nameformic acid
Traditional Nameformic acid
SMILESOC=O
InChI IdentifierInChI=1S/CH2O2/c2-1-3/h1H,(H,2,3)
InChI KeyBDAGIHXWWSANSR-UHFFFAOYSA-N
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0002-9000000000-5d27bb312e37a2c8994fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-0fmi-9200000000-2a89ba98485194acd75aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-0002-9000000000-a8fbddf8ca4197b30013View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-0002-9000000000-98310116f8a2d6a969ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-0002-9000000000-ec8753fd9790a3cf0be8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-0002-9000000000-121d1a025b72a70e412aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-0002-9000000000-5f1955dee7ab988e86ddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-0002-9000000000-f8e14272296ee06d19f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9000000000-092f816e62c8d2f5d56eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-eb2207f7400e9144fff7View in MoNA
MSMass Spectrum (Electron Ionization)splash10-004j-9000000000-2e63b0c1e2e417b0d747View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01942
HMDB IDHMDB0000142
FooDB IDFDB012804
Phenol Explorer IDNot Available
KNApSAcK IDC00001182
BiGG IDNot Available
BioCyc IDFORMATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFormic_acid
Chemspider IDNot Available
ChEBI ID30751
PubChem Compound ID284
Kegg Compound IDC00058
YMDB IDYMDB00385
ECMDB IDECMDB00142
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Finholt, Albert E.; Jacobson, Eugene C. The reduction of carbon dioxide to formic acid with lithium aluminum hydride. Journal of the American Chemical Society (1952), 74 3943-4.
2. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30.
3. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027.
4. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
5. Finholt, Albert E.; Jacobson, Eugene C. The reduction of carbon dioxide to formic acid with lithium aluminum hydride. Journal of the American Chemical Society (1952), 74 3943-4.
6. Ohmori S, Sumii I, Toyonaga Y, Nakata K, Kawase M: High-performance liquid chromatographic determination of formate as benzimidazole in biological samples. J Chromatogr. 1988 Apr 8;426(1):15-24.
7. Dal Pra I, Chiarini A, Boschi A, Freddi G, Armato U: Novel dermo-epidermal equivalents on silk fibroin-based formic acid-crosslinked three-dimensional nonwoven devices with prospective applications in human tissue engineering/regeneration/repair. Int J Mol Med. 2006 Aug;18(2):241-7.
8. Igeta Y, Kawarabayashi T, Sato M, Yamada N, Matsubara E, Ishiguro K, Kanai M, Tomidokoro Y, Osuga J, Okamoto K, Hirai S, Shoji M: Apolipoprotein E accumulates with the progression of A beta deposition in transgenic mice. J Neuropathol Exp Neurol. 1997 Nov;56(11):1228-35.
9. Kerns W 2nd, Tomaszewski C, McMartin K, Ford M, Brent J: Formate kinetics in methanol poisoning. J Toxicol Clin Toxicol. 2002;40(2):137-43.
10. Nagasawa H, Wada M, Koyama S, Kawanami T, Kurita K, Kato T: [A case of methanol intoxication with optic neuropathy visualized on STIR sequence of MR images]. Rinsho Shinkeigaku. 2005 Jul;45(7):527-30.
11. Foulon V, Sniekers M, Huysmans E, Asselberghs S, Mahieu V, Mannaerts GP, Van Veldhoven PP, Casteels M: Breakdown of 2-hydroxylated straight chain fatty acids via peroxisomal 2-hydroxyphytanoyl-CoA lyase: a revised pathway for the alpha-oxidation of straight chain fatty acids. J Biol Chem. 2005 Mar 18;280(11):9802-12. Epub 2005 Jan 11.
12. Iwamoto N, Nishiyama E, Ohwada J, Arai H: Distribution of amyloid deposits in the cerebral white matter of the Alzheimer's disease brain: relationship to blood vessels. Acta Neuropathol. 1997 Apr;93(4):334-40.
13. Ferrari LA, Arado MG, Nardo CA, Giannuzzi L: Post-mortem analysis of formic acid disposition in acute methanol intoxication. Forensic Sci Int. 2003 Apr 23;133(1-2):152-8.
14. Tasaka Y, Nakaya F, Matsumoto H, Iwamoto Y, Omori Y: Pancreatic amylin content in human diabetic subjects and its relation to diabetes. Pancreas. 1995 Oct;11(3):303-8.
15. D'Andrea MR, Reiser PA, Polkovitch DA, Gumula NA, Branchide B, Hertzog BM, Schmidheiser D, Belkowski S, Gastard MC, Andrade-Gordon P: The use of formic acid to embellish amyloid plaque detection in Alzheimer's disease tissues misguides key observations. Neurosci Lett. 2003 May 15;342(1-2):114-8.
16. Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811.
17. Berode M, Sethre T, Laubli T, Savolainen H: Urinary methanol and formic acid as indicators of occupational exposure to methyl formate. Int Arch Occup Environ Health. 2000 Aug;73(6):410-4.
18. Lehmann P, Kligman AM: In vivo removal of the horny layer with formic acid. Br J Dermatol. 1983 Sep;109(3):313-20.
19. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32.
20. Dunne VG, Bhattachayya S, Besser M, Rae C, Griffin JL: Metabolites from cerebrospinal fluid in aneurysmal subarachnoid haemorrhage correlate with vasospasm and clinical outcome: a pattern-recognition 1H NMR study. NMR Biomed. 2005 Feb;18(1):24-33.
21. Bloomer JC, Clarke SE, Chenery RJ: Determination of P4501A2 activity in human liver microsomes using [3-14C-methyl]caffeine. Xenobiotica. 1995 Sep;25(9):917-27.
22. Grady S, Osterloh J: Improved enzymic assay for serum formate with colorimetric endpoint. J Anal Toxicol. 1986 Jan-Feb;10(1):1-5.
23. Baumann K, Angerer J: Occupational chronic exposure to organic solvents. VI. Formic acid concentration in blood and urine as an indicator of methanol exposure. Int Arch Occup Environ Health. 1979 Jan 15;42(3-4):241-9.
24. Ferry DG, Temple WA, McQueen EG: Methanol monitoring. Comparison of urinary methanol concentration with formic acid excretion rate as a measure of occupational exposure. Int Arch Occup Environ Health. 1980;47(2):155-63.
25. Gupta A, Dwivedi M, Mahdi AA, Khetrapal CL, Bhandari M: Broad identification of bacterial type in urinary tract infection using (1)h NMR spectroscopy. J Proteome Res. 2012 Mar 2;11(3):1844-54. doi: 10.1021/pr2010692. Epub 2012 Jan 31.
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