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| formic acid |
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| CHEBI:30751 |
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| The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects. |
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This entity has been manually annotated by the ChEBI Team.
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CHEBI:42460, CHEBI:5145, CHEBI:24082
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| ChemicalBook:CB4854063, eMolecules:476327 |
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more structures >>
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| Formic acid (from Latin formica 'ant'), systematically named methanoic acid, is the simplest carboxylic acid. It has the chemical formula HCOOH and structure H−C(=O)−O−H. This acid 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 from methanol.
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Read full article at Wikipedia
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| InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) |
| BDAGIHXWWSANSR-UHFFFAOYSA-N |
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
astringent
A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions.
protic solvent
A polar solvent that is capable of acting as a hydron (proton) donor.
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View more via ChEBI Ontology
Acide formique
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ChemIDplus
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Ameisensäure
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ChemIDplus
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aminic acid
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ChemIDplus
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bilorin
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ChemIDplus
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Formic acid
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KEGG COMPOUND
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FORMIC ACID
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PDBeChem
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formylic acid
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ChemIDplus
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H‒COOH
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IUPAC
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HCO2H
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ChEBI
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HCOOH
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NIST Chemistry WebBook
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hydrogen carboxylic acid
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ChemIDplus
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Methanoic acid
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KEGG COMPOUND
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methoic acid
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ChEBI
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1008
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Gmelin Registry Number
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Gmelin
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1209246
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Reaxys Registry Number
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Reaxys
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64-18-6
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CAS Registry Number
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KEGG COMPOUND
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64-18-6
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CAS Registry Number
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NIST Chemistry WebBook
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64-18-6
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CAS Registry Number
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ChemIDplus
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Kang Y, Qi L, Li M, Diaz RE, Su D, Adzic RR, Stach E, Li J, Murray CB (2012)
Highly active Pt3Pb and core-shell Pt3Pb-Pt electrocatalysts for formic acid oxidation.
ACS nano 6, 2818-2825 [PubMed:22385261]
[show Abstract]
Formic acid is a promising chemical fuel for fuel cell applications. However, due to the dominance of the indirect reaction pathway and strong poisoning effects, the development of direct formic acid fuel cells has been impeded by the low activity of existing electrocatalysts at desirable operating voltage. We report the first synthesis of Pt(3)Pb nanocrystals through solution phase synthesis and show they are highly efficient formic acid oxidation electrocatalysts. The activity can be further improved by manipulating the Pt(3)Pb-Pt core-shell structure. Combined experimental and theoretical studies suggest that the high activity from Pt(3)Pb and the Pt-Pb core-shell nanocrystals results from the elimination of CO poisoning and decreased barriers for the dehydrogenation steps. Therefore, the Pt(3)Pb and Pt-Pb core-shell nanocrystals can improve the performance of direct formic acid fuel cells at desired operating voltage to enable their practical application. | Tormen L, Gil RA, Frescura VL, Martinez LD, Curtius AJ (2012)
The use of electrothermal vaporizer coupled to the inductively coupled plasma mass spectrometry for the determination of arsenic, selenium and transition metals in biological samples treated with formic acid.
Analytica chimica acta 717, 21-27 [PubMed:22304812]
[show Abstract]
A fast method for the determination of As, Co, Cu, Fe, Mn, Ni, Se and V in biological samples by ETV-ICP-MS, after a simple sample treatment with formic acid, is proposed. Approximately 75 mg of each sample is mixed with 5 mL of formic acid, kept at 90°C for 1 h and then diluted with nitric acid aqueous solution to a 5% (v/v) formic acid and 1% (v/v) nitric acid final concentrations. A palladium solution was used as a chemical modifier. The instrumental conditions, such as carrier gas flow rate, RF power, pyrolysis and vaporization temperatures and argon internal flow rate during vaporization were optimized. The formic acid causes a slight decrease of the analytes signal intensities, but does not increase the signal of the mainly polyatomic ions ((14)N(35)Cl(+), (14)N(12)C(+), (40)Ar(12)C(+), (13)C(37)Cl(+), (40)Ar(36)Ar(+), (40)Ar(35)Cl(+), (35)Cl(16)O(+), (40)Ar(18)O(+)) that affect the analytes signals. The effect of charge transfer reactions, that could increase the ionization efficiency of some elements with high ionization potentials was not observed due to the elimination of most of the organic compounds during the pyrolysis step. External calibration with aqueous standard solutions containing 5% (v/v) formic acid allows the simultaneous determination of all analytes with high accuracy. The detection limits in the samples were between 0.01 (Co) and 850 μg kg(-1) (Fe and Se) and the precision expressed by the relative standard deviations (RSD) were between 0.1% (Mn) and 10% (Ni). Accuracy was validated by the analysis of four certified reference biological materials of animal tissues (lobster hepatopancreas, dogfish muscle, oyster tissue and bovine liver). The recommended procedure avoids plasma instability, carbon deposit on the cones and does not require sample digestion. | Liu J, Zeng X, Cheng M, Yun J, Li Q, Jing Z, Jin F (2012)
Reduction of formic acid to methanol under hydrothermal conditions in the presence of Cu and Zn.
Bioresource technology 114, 658-662 [PubMed:22483350]
[show Abstract]
Formic acid is the main breakdown product of mild hydrothermal treatment of carbohydrates. Further conversion to methanol was achieved using Cu as catalyst and Zn as reductant under hydrothermal conditions of 250-325 °C for 3-12 h. Both Cu and Zn used were commercial Cu and Zn powders with particle sizes of 200 mesh. A methanol yield of 32% was achieved at 300 °C for 5h with 6.5 mmol of Cu, 12 mmol of Zn and a filling rate of 44%. Thus, this process may provide a promising solution to producing methanol from biomass by converting carbohydrates into formic acid. | Feng L, Sun X, Liu C, Xing W (2012)
Poisoning effect diminished on a novel PdHoOx/C catalyst for the electrooxidation of formic acid.
Chemical communications (Cambridge, England) 48, 419-421 [PubMed:22080171]
[show Abstract]
A surprisingly high and stable current was observed after the peak current on the PdHoOx/C catalyst indicating the diminished poisoning effect. Moreover, the novel PdHoOx/C catalyst exhibited excellent catalytic activity and stability for formic acid oxidation due to the large electrochemical surface area and electronic effect. | Bulushev DA, Jia L, Beloshapkin S, Ross JR (2012)
Improved hydrogen production from formic acid on a Pd/C catalyst doped by potassium.
Chemical communications (Cambridge, England) 48, 4184-4186 [PubMed:22447125]
[show Abstract]
The rate of hydrogen production from vapour-phase formic acid decomposition can be increased by 1-2 orders of magnitude by doping a Pd/C catalyst with potassium ions. Surface potassium formate and/or bicarbonate species could be involved in the rate-determining step of this reaction. | Martindale BC, Compton RG (2012)
Formic acid electro-synthesis from carbon dioxide in a room temperature ionic liquid.
Chemical communications (Cambridge, England) 48, 6487-6489 [PubMed:22622393]
[show Abstract]
The novel synthesis of formic acid has been achieved in a room temperature ionic liquid via the reaction of electro-activated carbon dioxide and protons on pre-anodised platinum. Only mild reaction conditions of room temperature and 1 atm CO(2) were used. This work highlights the effect of pre-anodisation on Pt surfaces. | Li J, Ding DJ, Deng L, Guo QX, Fu Y (2012)
Catalytic air oxidation of biomass-derived carbohydrates to formic acid.
ChemSusChem 5, 1313-1318 [PubMed:22499553]
[show Abstract]
An efficient catalytic system for biomass oxidation to form formic acid was developed. The conversion of glucose to formic acid can reach up to 52% yield within 3 h when catalyzed by 5 mol% of H(5)PV(2)Mo(10)O(40) at only 373 K using air as the oxidant. Furthermore, the heteropolyacid can be used as a bifunctional catalyst in the conversion of cellulose to formic acid (yield=35%) with air as the oxidant. | Motokura K, Kashiwame D, Miyaji A, Baba T (2012)
Copper-catalyzed formic acid synthesis from CO2 with hydrosilanes and H2O.
Organic letters 14, 2642-2645 [PubMed:22540994]
[show Abstract]
A copper-catalyzed formic acid synthesis from CO2 with hydrosilanes has been accomplished. The Cu(OAc)2·H2O-1,2-bis(diphenylphosphino)benzene system is highly effective for the formic acid synthesis under 1 atm of CO2. The TON value approached 8100 in 6 h. The reaction pathway was revealed by in situ NMR analysis and isotopic experiments. | Marushkevich K, Khriachtchev L, Räsänen M, Melavuori M, Lundell J (2012)
Dimers of the higher-energy conformer of formic acid: experimental observation.
The journal of physical chemistry. A 116, 2101-2108 [PubMed:22280475]
[show Abstract]
We report on the first experimental observation of formic acid dimers composed of two molecules of the higher-energy cis conformer. The cis-cis formic acid dimers are prepared in an argon matrix by selective vibrational excitation of the ground state trans conformer (deuterated form HCOOD) combined with thermal annealing of the matrix at about 30 K. Five cis-cis formic acid dimers are predicted by ab initio calculations (interaction energies from -16.9 to -27.2 kJ mol(-1)), and these structures are used for the assignment of the experimental spectra. Selective vibrational excitation of the obtained cis-cis dimers leads to the formation of several trans-cis dimers, which supports the proposed assignments. | Arruda MS, Marinho RR, Maniero AM, Mundin MS, Mocellin A, Pilling S, de Brito AN, Prudente FV (2012)
Theoretical-experimental study of formic acid photofragmentation in the valence region.
The journal of physical chemistry. A 116, 6693-6701 [PubMed:22606986]
[show Abstract]
Photoionization and photofragmentation studies of formic acid (HCOOH) are performed for the valence shell electron ionization process. The total and partial ion yield of gaseous HCOOH were collected as a function of photon energy in the ultraviolet region, between 11.12 and 19.57 eV. Measurements of the total and partial ion yield of gaseous formic acid molecule are performed with a time-of-flight mass spectrometer at the Synchrotron Light Brazilian Laboratory. Density functional theory and time dependent density functional theory are employed to calculate the ground and excited electronic state energies of neutral and ionic formic acid as well as their fragments and normal vibration modes. The ionization potential energies, the stability of electronic excited states of HCOOH(+), and the energies of opening fragmentation channels are estimated from theoretical-experimental analysis. Additionally, the main formic acid photofragmentation pathways by exposition of photons within that energy range are determined experimentally. These produced ions primarily have the following mass/charge ratios: 46 (HCOOH(+)), 45 (COOH(+)), 29 (HCO(+)), and 18 (H(2)O(+)). | Wallage HR, Watterson JH (2008)
Formic acid and methanol concentrations in death investigations.
Journal of analytical toxicology 32, 241-247 [PubMed:18397576]
[show Abstract]
Methanol ingestion results in the formation of formic acid, a toxic metabolite that can cause metabolic acidosis. Methanol toxicity is therefore dependent on the amount of methanol ingested, the nature of treatment received, elapsed time since ingestion, and the accumulation of formic acid. Both methanol and formic acid concentrations are determined at this laboratory using headspace gas chromatography. An examination of 12 fatalities attributed to methanol poisoning is presented. Six individuals were found deceased, and their postmortem methanol and formic acid concentrations ranged from 84 to 543 mg/dL and 64 to 110 mg/dL, respectively. In the other six individuals, hospital treatment such as bicarbonate, ethanol infusion, and hemodialysis was administered. Antemortem methanol and formic acid concentrations ranged from 68 to 427 mg/dL and 37 to 91 mg/dL, respectively, whereas corresponding postmortem methanol and formic acid levels ranged from undetectable to 49 mg/dL and undetectable to 48 mg/dL, respectively. Hospital treatment of formic acid toxicity resulted in significantly reduced postmortem methanol and formic acid concentrations. Furthermore, the toxicological relevance of nine methanol-positive cases where postmortem methanol concentrations ranged from 3 to 142 mg/dL, with corresponding formic acid levels of less than 10 mg/dL, is discussed. | Kapur BM, Vandenbroucke AC, Adamchik Y, Lehotay DC, Carlen PL (2007)
Formic acid, a novel metabolite of chronic ethanol abuse, causes neurotoxicity, which is prevented by folic acid.
Alcoholism, clinical and experimental research 31, 2114-2120 [PubMed:18034701]
[show Abstract]
BackgroundMethanol is endogenously formed in the brain and is present as a congener in most alcoholic beverages. Because ethanol is preferentially metabolized over methanol (MeOH) by alcohol dehydrogenase, it is not surprising that MeOH accumulates in the alcohol-abusing population. This suggests that the alcohol-drinking population will have higher levels of MeOH's neurotoxic metabolite, formic acid (FA). FA elimination is mediated by folic acid. Neurotoxicity is a common result of chronic alcoholism. This study shows for the first time that FA, found in chronic alcoholics, is neurotoxic and this toxicity can be mitigated by folic acid administration.ObjectiveTo determine if FA levels are higher in the alcohol-drinking population and to assess its neurotoxicity in organotypic hippocampal rat brain slice cultures.MethodsSerum and CSF FA was measured in samples from both ethanol abusing and control patients, who presented to a hospital emergency department. FA's neurotoxicity and its reversibility by folic acid were assessed using organotypic rat brain hippocampal slice cultures using clinically relevant concentrations.ResultsSerum FA levels in the alcoholics (mean +/- SE: 0.416 +/- 0.093 mmol/l, n = 23) were significantly higher than in controls (mean +/- SE: 0.154 +/- 0.009 mmol/l, n = 82) (p < 0.0002). FA was not detected in the controls' CSF (n = 20), whereas it was >0.15 mmol/l in CSF of 3 of the 4 alcoholic cases. Low doses of FA from 1 to 5 mmol/l added for 24, 48 or 72 hours to the rat brain slice cultures caused neuronal death as measured by propidium iodide staining. When folic acid (1 micromol/l) was added with the FA, neuronal death was prevented.ConclusionsFormic acid may be a significant factor in the neurotoxicity of ethanol abuse. This neurotoxicity can be mitigated by folic acid administration at a clinically relevant dose. | Muthuvel A, Rajamani R, Manikandan S, Sheeladevi R (2006)
Detoxification of formate by formate dehydrogenase-loaded erythrocytes and carbicarb in folate-deficient methanol-intoxicated rats.
Clinica chimica acta; international journal of clinical chemistry 367, 162-169 [PubMed:16445901]
[show Abstract]
BackgroundFormic acid is a toxic metabolite responsible for the metabolic acidosis in methanol poisoning. Formate dehydrogenase (EC 1.2.1.2) converts formate into CO2 in the presence of NAD. We examined the in vitro and in vivo efficiency of formate dehydrogenase-loaded carrier erythrocytes along with carbicarb in eliminating the formate in methanol-intoxicated folate-deficient rats.MethodFormate dehydrogenase-loaded erythrocytes were prepared by hypotonic dialysis method. Carbicarb (carb) (equimolar solution of sodium carbonate and sodium bicarbonate) was used to treat metabolic acidosis. Folate depletion was induced by methotrexate (MTX) treatment. Experimental design consisted of 8 groups: saline control, methanol control, MTX control, ELE control, MTX-methanol control, MTX-methanol-carb, MTX-methanol-carb-ELE, and MTX-MeOH-ELE group. Male Wistar rats treated with MTX (0.3 mg/kg) for a week were injected (i.p.) with methanol (4 g/kg). Twelve hours later, the carbicarb solution was infused, and then a formate dehydrogenase-loaded erythrocytes suspension (40% hematocrit) was infused (i.v.) in bolus. Blood samples were collected every hour for 4 h from the cannulated left jugular vein. Blood methanol and formate were estimated respectively with HPLC and fluorimetric assay. Blood pH, blood pO2, pCO2 and bicarbonate were also measured.ResultsThere was marked elimination of formate in selected groups.ConclusionFormate dehydrogenase-loaded erythrocytes, along with carbicarb, facilitates removal of formate, in methanol poisoning. | Muthuvel A, Rajamani R, Sheeladevi R (2006)
Therapeutic response to single intravenous bolus administration of formate dehydrogenase in methanol-intoxicated rats.
Toxicology letters 161, 89-95 [PubMed:16185830]
[show Abstract]
Methanol remains to be a major public and environmental health hazard. Formic acid is the toxic metabolite responsible for the metabolic acidosis observed in methanol poisoning in humans, in non-human primates and in folate-depleted rodents. Cytochrome oxidase inhibition by formate leads to lactic acid accumulation, which contributes significantly to metabolic acidosis. Toxic effects in human beings are characterized by formic acidemia, metabolic acidosis, ocular toxicity, nervous system depression, blindness, coma and death. Elimination of formate is one of the principles of management in methanol poisoning. Hemodialysis facility is not readily available in all the places, in developing countries like India. Formate dehydrogenase (EC 1.2.1.2) acts directly over formate and converts formate into CO(2) in the presence of NAD. Effect of single intravenous bolus infusion of formate dehydrogenase, obtained from Candida boidinii; in methanol-intoxicated folate deficient rat model was evaluated. Folate depletion induced by methotrexate (MTX) treatment. Carbicarb (Carb) (equimolar solution of sodium carbonate and sodium bicarbonate) was used to treat metabolic acidosis. Experimental design consists of seven groups, namely Saline control, methanol control, MTX control, Enzyme control, MTX-methanol control, MTX-methanol-Carb and MTX-methanol-Carb-Enz group. Male wistar rats treated with MTX (0.3mg/kg) for a week, were injected (i.p.) with methanol (4 gm/kg), 12h latter, Carbicarb solution was infused, following this enzyme was infused (i.v.) in bolus. Blood samples were collected every 15 min for an hour from the cannulated left jugular vein and blood methanol, formate were estimated, respectively, with HPLC and fluorimetric assay. Blood pH, blood gases pO(2), pCO(2) and bicarbonate were monitored with blood gas analyzer in order to evaluate acid base status of the animal. Results obtained show that there is significant elimination of formate within 15 min. It may be concluded that single bolus infusion of formate dehydrogenase facilitates fast removal of formate, a highly toxic metabolite in methanol poisoning. | Théfenne H, Turc J, Carmoi T, Gardet V, Renard C (2005)
[Acute methanol poisoning: about one case].
Annales de biologie clinique 63, 556-560 [PubMed:16230297]
[show Abstract]
In this article, we report a case of metabolic coma with acidosis and elevated anion gap. The etiological investigation requires laboratory findings because clinical features are not enough specific in the early stage of intoxication. Measurement of methanol and formic acid, its toxic metabolite, is useful in confirming the diagnosis. The major differential diagnosis to discuss is ethylene glycol poisoning. Methanol poisoning is rare but potentially fatal; the toxicity of methanol is clearly correlated to the degree of metabolic acidosis. Formic acid accumulation is also associated with an increased risk for ocular and neurologic dysfunction. For preventing permanent visual damage, the acidosis should be corrected by antidotal treatment or haemodialysis in severe poisoning. | Hantson PE (2005)
[Acute methanol intoxication: physiopathology, prognosis and treatment].
Bulletin et memoires de l'Academie royale de medecine de Belgique 160, 294-300 [PubMed:16465784]
[show Abstract]
Acute methanol poisoning is still complicated by a poor vital or visual prognosis. The pathophysiology of methanol poisoning is not yet fully understood. It appears that the major toxic effects are related to the main metabolite of methanol, formic acid. The central nervous system and the visual pathway are the main targets of methanol poisoning. When irreversible brain lesions occur, the diagnosis of brain death can be made. Other organs, like the pancreas or the kidney, may also be damaged according to the severity of metabolic acidosis; however, the toxic manifestations are in this case mostly reversible. The historical treatment of methanol poisoning relies on ethanol administration. However, ethanol therapy has numerous side effects and a new antidote, fomepizole, that was previously approved for the treatment of ethylene glycol poisoning, appears effective, safe and easy to use. Hemodialysis remains effective for the removal of both methanol and formic acid. | Buvári-Barcza A, Tóth I, Barcza L (2005)
Anhydrous formic acid and acetic anhydride as solvent or additive in nonaqueous titrations.
Die Pharmazie 60, 650-655 [PubMed:16222862]
[show Abstract]
The use and importance of formic acid and acetic anhydride (Ac2O) is increasing in nonaqueous acid-base titrations, but their interaction with the solutes is poorly understood. This paper attempts to clarify the effect of the solvents; NMR and spectrophotometric investigations were done to reveal the interactions between some bases and the mentioned solvents. Anhydrous formic acid is a typical protogenic solvent but both the relative permittivity and acidity are higher than those of acetic acid (mostly used in assays of bases). These differences originate from the different chemical structures: liquid acetic acid contains basically cyclic dimers while formic acid forms linear associates. Ac2O is obviously not an acidic but an aprotic (very slightly protophilic) solvent, which supposedly dissociates slightly into acetyl (CH3CO+) and acetate (AcO-) ions. In fact, some bases react with Ac2O forming an associate: the Ac+ group is bound to the delta- charged atom of the reactant while AcO- is associated with the delta+ group at appropriate distance. | Alemdar A, Iridag Y, Kazanci M (2005)
Flow behavior of regenerated wool-keratin proteins in different mediums.
International journal of biological macromolecules 35, 151-153 [PubMed:15811469]
[show Abstract]
Keratin is abundantly present in nature and the major component of hair, wool, feather, nail and horns. Dissolution of keratin is often required when non-textile applications are demanded. However, the low solubility of keratin in water is the major problem. It becomes unstable and precipitated when stored for a long time. Therefore, it is necessary to find a good solvent that provides high stability and easy processibility. In this research, we used formic acid and dimethylformamide (DMF) to dissolve regenerated keratin protein films. It is shown that formic acid is a good solvent for regenerated keratin proteins for the purpose of storage. Transparent and stable regenerated keratin solution is obtained in formic acid. | Eells JT, Wong-Riley MT, VerHoeve J, Henry M, Buchman EV, Kane MP, Gould LJ, Das R, Jett M, Hodgson BD, Margolis D, Whelan HT (2004)
Mitochondrial signal transduction in accelerated wound and retinal healing by near-infrared light therapy.
Mitochondrion 4, 559-567 [PubMed:16120414]
[show Abstract]
Photobiomodulation by light in the red to near infrared range (630-1000 nm) using low energy lasers or light-emitting diode (LED) arrays has been shown to accelerate wound healing, improve recovery from ischemic injury in the heart and attenuate degeneration in the injured optic nerve. Recent evidence indicates that the therapeutic effects of red to near infrared light result, in part, from intracellular signaling mechanisms triggered by the interaction of NIR light with the mitochondrial photoacceptor molecule cytochrome c oxidase. We have demonstrated that NIR-LED photo-irradiation increases the production of cytochrome oxidase in cultured primary neurons and reverses the reduction of cytochrome oxidase activity produced by metabolic inhibitors. We have also shown that NIR-LED treatment prevents the development of oral mucositis in pediatric bone marrow transplant patients. Photobiomodulation improves wound healing in genetically diabetic mice by upregulating genes important in the promotion of wound healing. More recent studies have provided evidence for the therapeutic benefit of NIR-LED treatment in the survival and functional recovery of the retina and optic nerve in vivo after acute injury by the mitochondrial toxin, formic acid generated in the course of methanol intoxication. Gene discovery studies conducted using microarray technology documented a significant upregulation of gene expression in pathways involved in mitochondrial energy production and antioxidant cellular protection. These findings provide a link between the actions of red to near infrared light on mitochondrial oxidative metabolism in vitro and cell injury in vivo. Based on these findings and the strong evidence that mitochondrial dysfunction is involved in the pathogenesis of numerous diseases processes, we propose that NIR-LED photobiomodulation represents an innovative and non-invasive therapeutic approach for the treatment of tissue injury and disease processes in which mitochondrial dysfunction is postulated to play a role including diabetic retinopathy, age-related macular degeneration, Leber's hereditary optic neuropathy and Parkinson's disease. | Treichel JL, Henry MM, Skumatz CM, Eells JT, Burke JM (2003)
Formate, the toxic metabolite of methanol, in cultured ocular cells.
Neurotoxicology 24, 825-834 [PubMed:14637377]
[show Abstract]
Methanol has neurotoxic actions on the human retina due to its metabolite, formic acid, which is a mitochondrial toxin. In methanol poisoned animals, morphologic changes were seen both in retinal photoreceptors and in cells of the underlying retinal pigment epithelium (RPE). Here the effects of formate exposure on the two retinal cell types were analyzed in more detail in vitro using photoreceptor (661W) and RPE (ARPE-19) cell lines. Cells were exposed for time courses from minutes to days to sodium formate at pH 7.4 or to formic acid at pH 6.8, to simulate the metabolic acidosis that accompanies methanol poisoning. Formate accumulation, cellular ATP, cytotoxicity (lactate dehydrogenase (LDH) release) and cell phenotype were analyzed. Formate accumulated with a similar biphasic pattern in both cell types, and to similar levels whether delivered as sodium formate or as formic acid. ATP changes with sodium formate treatment differed between cell types with only 661W cells showing a rapid (within minutes), transient ATP increase. The subsequent ATP decrease was earlier in 661W cells (6 h) than the ATP decrease in ARPE-19 cells (24 h), and although both cell types showed evidence of cytotoxicity, the effects were greater for 661W cells. Both cell types showed enhanced morphologic and biochemical changes with formic acid treatment including earlier and/or greater effects on ATP depletion and cytotoxicity; again effects were more pronounced in 661W cells. Formate therefore is toxic for both cell lines, with 661W cells exhibiting greater sensitivity. Medium pH also appears to play a significant role in formate toxicity in vitro. | Iuchi S, Hoffner G, Verbeke P, Djian P, Green H (2003)
Oligomeric and polymeric aggregates formed by proteins containing expanded polyglutamine.
Proceedings of the National Academy of Sciences of the United States of America 100, 2409-2414 [PubMed:12591956]
[show Abstract]
Neurological diseases resulting from proteins containing expanded polyglutamine (polyQ) are characteristically associated with insoluble neuronal inclusions, usually intranuclear, and neuronal death. We describe here oligomeric and polymeric aggregates formed in cells by expanded polyQ. These aggregates are not dissociated by concentrated formic acid, an extremely effective solvent for otherwise insoluble proteins. Perinuclear inclusions formed in cultured cells by expanded polyQ can be completely dissolved in concentrated formic acid, but a soluble protein oligomer containing the expanded polyQ and released by the formic acid is not dissociated to monomer. In Huntington's disease, a formic acid-resistant oligomer is present in cerebral cortex, but not in cerebellum. Cortical nuclei contain a polymeric aggregate of expanded polyQ that is insoluble in formic acid, does not enter polyacrylamide gels, but is retained on filters. This finding shows that the process of polymerization is more advanced in the cerebral cortex than in cultured cells. The resistance of oligomer and polymer to formic acid suggests the participation of covalent bonds in their stabilization. | Osterloh JD, Pond SM, Grady S, Becker CE (1986)
Serum formate concentrations in methanol intoxication as a criterion for hemodialysis.
Annals of internal medicine 104, 200-203 [PubMed:3946945]
[show Abstract]
To evaluate the utility of serum formate concentrations, four patients were studied after ingestion of a methanolic copying fluid. All patients were initially intoxicated. Twelve to twenty-four hours later, signs and symptoms included nausea, abdominal pain, hypokalemia, acidosis (three patients), and pathologic ocular findings (two patients). All patients were treated with ethanol and folate. The two patients with ocular signs and acidosis had high serum formate concentrations (75 and 55 mg/dL, respectively). One of the two patients had a high methanol concentration (222 mg/dL) and required hemodialysis; the other patient did not (methanol concentration, 24 mg/dL). In the other two patients without ocular signs, initial formate concentrations were undetectable (limit of detection, 0.5 mg/dL); however, one patient required hemodialysis because the methanol concentration was 72 mg/dL. Formate is the mediator of ocular injury and acidosis. In these patients formate concentrations correlated with the clinical condition but methanol concentrations did not. | McMartin KE, Ambre JJ, Tephly TR (1980)
Methanol poisoning in human subjects. Role for formic acid accumulation in the metabolic acidosis.
The American journal of medicine 68, 414-418 [PubMed:7361809]
[show Abstract]
Whereas a great deal of information is available on the etiology of methanol poisoning in the monkey, very little study has been made in human subjects. The role of formic acid in methanol toxicity in human subjects has not been established. Two patients have been studied who have presented with the characteristics of methanol poisoning--metabolic acidosis and ocular toxicity. This has made possible a confirmation of the role of formate in the toxic syndrome. Acidosis was very severe in both cases with arterial pH values of about 6.9 and plasma bicarbonate concentrations of 3 meq/liter. A sensitive and specific assay was used to measure formic acid levels in blood and other fluids. Formate accumulation was marked with initial blood levels ranging from 11.1 to 26.0 meq/liter. Decreases in blood bicarbonate concentrations of similar magnitude coincided with the increase in formate. Thus, accumulation of formic acid plays a major part in the acidosis observed in human subjects poisoned with methanol, as has been demonstrated in monkeys. Treatment involving bicarbonate administration, ethanol infusion and hemodialysis, rapidly decreased formate levels in the blood to control values. Methanol concentrations were reduced but to lesser extent than that of formate. Despite the reduction in formate and methanol concentrations in both cases, the treatment was successful in only one of the two patients. |
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