| Record Information |
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| Version | 2.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2022-01-20 19:53:13 UTC |
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| NP-MRD ID | NP0000316 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Formic acid |
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| Description | Formic acid is the simplest carboxylic acid. 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 byproduct 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. |
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| Structure | InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) |
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| Synonyms | | Value | Source |
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| Acide formique | ChEBI | | Ameisensaeure | ChEBI | | Aminic acid | ChEBI | | Bilorin | ChEBI | | Formylic acid | ChEBI | | H-COOH | ChEBI | | HCO2H | ChEBI | | HCOOH | ChEBI | | Hydrogen carboxylic acid | ChEBI | | Methanoic acid | ChEBI | | Methoic acid | ChEBI | | Aminate | Generator | | Formylate | Generator | | Hydrogen carboxylate | Generator | | Methanoate | Generator | | Methoate | Generator | | Formate | Generator | | Add-F | HMDB | | Ameisensaure | HMDB | | Collo-bueglatt | HMDB | | Collo-didax | HMDB | | Formira | HMDB | | Formisoton | HMDB | | Methanoic acid monomer | HMDB | | Myrmicyl | HMDB | | Sodium formate | HMDB | | Sybest | HMDB | | Wonderbond hardener m 600l | HMDB | | Calcium formate | HMDB | | Cobalt(II) formate dihydrate | HMDB | | Formic acid, aluminum salt | HMDB | | Formic acid, copper salt | HMDB | | Formic acid, cromium (+3) salt | HMDB | | Lithium formate | HMDB | | Ammonium formate | HMDB | | Formic acid, ammonium (4:1) salt | HMDB | | Formic acid, ammonium salt | HMDB | | Formic acid, calcium salt | HMDB | | Formic acid, copper (+2) salt | HMDB | | Formic acid, lead (+2) salt | HMDB | | Formic acid, lead salt | HMDB | | Formic acid, nickel salt | HMDB | | Formic acid, potassium salt | HMDB | | Formic acid, strontium salt | HMDB | | Mafusol | HMDB | | Ammonium tetraformate | HMDB | | Formic acid, 14C-labeled | HMDB | | Formic acid, cobalt (+2) salt | HMDB | | Formic acid, copper, ammonium salt | HMDB | | Formic acid, sodium salt | HMDB | | Formic acid, sodium salt, 14C-labeled | HMDB | | Formic acid, ammonium (2:1) salt | HMDB | | Formic acid, cadmium salt | HMDB | | Formic acid, cesium salt | HMDB | | Formic acid, copper, nickel salt | HMDB | | Formic acid, cromium (+3), sodium (4:1:1) salt | HMDB | | Formic acid, lithium salt | HMDB | | Formic acid, magnesium salt | HMDB | | Formic acid, nickel (+2) salt | HMDB | | Formic acid, rubidium salt | HMDB | | Formic acid, sodium salt, 13C-labeled | HMDB | | Formic acid, thallium (+1) salt | HMDB | | Formic acid, zinc salt | HMDB | | Nickel formate dihydrate | HMDB | | Aluminum formate | HMDB | | Potassium formate | HMDB | | Strontium formate | HMDB | | Lead formate | HMDB | | Nickel formate | HMDB | | Chromic formate | HMDB | | Cobaltous formate | HMDB | | Cupric formate | HMDB | | Magnesium formate | HMDB | | Zinc formate | HMDB |
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| Chemical Formula | CH2O2 |
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| Average Mass | 46.0254 Da |
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| Monoisotopic Mass | 46.00548 Da |
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| IUPAC Name | formic acid |
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| Traditional Name | formic acid |
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| CAS Registry Number | 64-18-6 |
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| SMILES | OC=O |
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| InChI Identifier | InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) |
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| InChI Key | BDAGIHXWWSANSR-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, simulated) | v.dorna83@yahoo.com | Not Available | Not Available | 2021-07-29 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Carboxylic acids |
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| Direct Parent | Carboxylic acids |
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| Alternative Parents | |
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| Substituents | - Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 8.4 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1000 mg/mL | Not Available | | LogP | -0.54 | Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995). |
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| Predicted Properties | |
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| General References | - 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. [PubMed:3384868 ]
- 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. [PubMed:16820930 ]
- 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. [PubMed:9370233 ]
- 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. [PubMed:12126185 ]
- 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. [PubMed:16119839 ]
- 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. [PubMed:15644336 ]
- 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. [PubMed:9113198 ]
- 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. [PubMed:12742704 ]
- 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. [PubMed:8577686 ]
- 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. [PubMed:12727331 ]
- 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. [PubMed:11007345 ]
- Lehmann P, Kligman AM: In vivo removal of the horny layer with formic acid. Br J Dermatol. 1983 Sep;109(3):313-20. [PubMed:6615718 ]
- 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. [PubMed:8553685 ]
- Grady S, Osterloh J: Improved enzymic assay for serum formate with colorimetric endpoint. J Anal Toxicol. 1986 Jan-Feb;10(1):1-5. [PubMed:3754027 ]
- 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. [PubMed:422265 ]
- 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. [PubMed:7440001 ]
- Hasunuma T, Sung KM, Sanda T, Yoshimura K, Matsuda F, Kondo A: Efficient fermentation of xylose to ethanol at high formic acid concentrations by metabolically engineered Saccharomyces cerevisiae. Appl Microbiol Biotechnol. 2011 May;90(3):997-1004. doi: 10.1007/s00253-011-3085-x. Epub 2011 Jan 19. [PubMed:21246355 ]
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