Fluorocitric acid

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Fluorocitric acid
Fluorocitric acid.svg
Names
IUPAC name
3-C-Carboxy-2,4-dideoxy-2-fluoropentaric acid
Other names
2-Fluorocitric acid; 2-Fluorocitrate; 1-Fluoro-2-hydroxypropane-1,2,3-tricarboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C6H7FO7/c7-3(4(10)11)6(14,5(12)13)1-2(8)9/h3,14H,1H2,(H,8,9)(H,10,11)(H,12,13) Yes check.svgY
    Key: DGXLYHAWEBCTRU-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H7FO7/c7-3(4(10)11)6(14,5(12)13)1-2(8)9/h3,14H,1H2,(H,8,9)(H,10,11)(H,12,13)
    Key: DGXLYHAWEBCTRU-UHFFFAOYAE
  • O=C(O)C(O)(CC(=O)O)C(F)C(=O)O
Properties
HOC(CO2H)(CH2CO2H)(CHFCO2H)
Molar mass 210.113 g·mol−1
AppearanceOdorless, white crystals
Density 1.37 g/cm3
Melting point 35.2 °C (95.4 °F; 308.3 K)
Boiling point 165 °C (329 °F; 438 K)
Soluble
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fluorocitric acid is an organic compound with the chemical formula H O C(CO2H)(CH2CO2H)(CHFCO2H). It is a fluorinated carboxylic acid derived from citric acid by substitution of one methylene hydrogen by a fluorine atom. The appropriate anion is called fluorocitrate. Fluorocitrate is formed in two steps from fluoroacetate. Fluoroacetate is first converted to fluoroacetyl-CoA by acetyl-CoA synthetase in the mitochondria. Then fluoroacetyl-CoA condenses with oxaloacetate to form fluorocitrate. This step is catalyzed by citrate synthase. [1] Flurocitrate is a metabolite of fluoroacetic acid and is very toxic because it is not processable using aconitase in the citrate cycle (where fluorocitrate takes place of citrate as the substrate). The enzyme is inhibited and the cycle stops working. [2]

Contents

See also

Related Research Articles

<span class="mw-page-title-main">Citric acid cycle</span> Interconnected biochemical reactions releasing energy

The citric acid cycle—also known as the Krebs cycle, Szent–Györgyi–Krebs cycle or the TCA cycle (tricarboxylic acid cycle)—is a series of biochemical reactions to release the energy stored in nutrients through the oxidation of acetyl-CoA derived from carbohydrates, fats, and proteins. The chemical energy released is available under the form of ATP. The Krebs cycle is used by organisms that respire (as opposed to organisms that ferment) to generate energy, either by anaerobic respiration or aerobic respiration. In addition, the cycle provides precursors of certain amino acids, as well as the reducing agent NADH, that are used in numerous other reactions. Its central importance to many biochemical pathways suggests that it was one of the earliest components of metabolism. Even though it is branded as a "cycle", it is not necessary for metabolites to follow only one specific route; at least three alternative segments of the citric acid cycle have been recognized.

<span class="mw-page-title-main">Citric acid</span> Weak organic acid

Citric acid is an organic compound with the chemical formula HOC(CO2H)(CH2CO2H)2. It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry, it is an intermediate in the citric acid cycle, which occurs in the metabolism of all aerobic organisms.

<span class="mw-page-title-main">Acetyl-CoA</span> Chemical compound

Acetyl-CoA is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle to be oxidized for energy production.

<span class="mw-page-title-main">Malic acid</span> Dicarboxylic acid responsible for apple acidity

Malic acid is an organic compound with the molecular formula HO2CCH(OH)CH2CO2H. It is a dicarboxylic acid that is made by all living organisms, contributes to the sour taste of fruits, and is used as a food additive. Malic acid has two stereoisomeric forms, though only the L-isomer exists naturally. The salts and esters of malic acid are known as malates. The malate anion is a metabolic intermediate in the citric acid cycle.

<span class="mw-page-title-main">Oxaloacetic acid</span> Organic compound

Oxaloacetic acid (also known as oxalacetic acid or OAA) is a crystalline organic compound with the chemical formula HO2CC(O)CH2CO2H. Oxaloacetic acid, in the form of its conjugate base oxaloacetate, is a metabolic intermediate in many processes that occur in animals. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle.

<span class="mw-page-title-main">Sodium fluoroacetate</span> Chemical compound

Sodium fluoroacetate, also known as compound 1080, is an organofluorine chemical compound with the chemical formula FCH2CO2Na. It is the sodium salt of fluoroacetic acid. It contains sodium cations Na+ and fluoroacetate anions FCH2CO−2. This colourless salt has a taste similar to that of table salt and is used as a rodenticide.

Fluoroacetate may refer to:

Fatty acid metabolism consists of various metabolic processes involving or closely related to fatty acids, a family of molecules classified within the lipid macronutrient category. These processes can mainly be divided into (1) catabolic processes that generate energy and (2) anabolic processes where they serve as building blocks for other compounds.

<span class="mw-page-title-main">Aconitase</span> Class of enzymes

Aconitase is an enzyme that catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle, a non-redox-active process.

<span class="mw-page-title-main">Citrate synthase</span> Enzyme found in humans

The enzyme citrate synthase E.C. 2.3.3.1 ] exists in nearly all living cells and stands as a pace-making enzyme in the first step of the citric acid cycle. Citrate synthase is localized within eukaryotic cells in the mitochondrial matrix, but is encoded by nuclear DNA rather than mitochondrial. It is synthesized using cytoplasmic ribosomes, then transported into the mitochondrial matrix.

<span class="mw-page-title-main">Fluoroacetic acid</span> Chemical compound

Fluoroacetic acid is a organofluorine compound with the chemical formula FCH2CO2H. It is a colorless solid that is noted for its relatively high toxicity. The conjugate base, fluoroacetate occurs naturally in at least 40 plants in Australia, Brazil, and Africa. It is one of only five known organofluorine-containing natural products.

<span class="mw-page-title-main">Ammonium ferric citrate</span> Chemical compound

Ammonium ferric citrate has the formula [NH+4]5[Fe(C6H4O7)2]5−. The iron in this compound is trivalent. All three carboxyl groups and the central hydroxyl group of citric acid are deprotonated. A distinguishing feature of this compound is that it is very soluble in water, in contrast to ferric citrate which is not very soluble.

In enzymology, a citrate—CoA ligase is an enzyme that catalyzes the chemical reaction

<i>Dichapetalum cymosum</i> Species of plant

Dichapetalum cymosum, commonly known as gifblaar from Afrikaans, or occasionally by its English translation, poison leaf, is a small prostrate shrub occurring in northern parts of Southern Africa in the family Dichapetalaceae. It is notable as a common cause of lethal cattle poisoning in this region and is considered one of the 'big 6' toxic plants of cattle in South Africa. A 1996 estimate of plant poisonings in South Africa attributes 8% of cattle mortality caused by poisonous plants to it. The majority (70%) of fatal cases are in Limpopo province, with 10% each in North West, Mpumalanga, and Gauteng. Fluoroacetate, the poison used to synthetically produce Compound 1080 used extensively in New Zealand, occurs in all parts of the plant and is responsible for the toxic effects shown.

<span class="mw-page-title-main">1,3-Difluoro-2-propanol</span> Chemical compound

1,3-Difluoro-2-propanol is a metabolic poison which disrupts the citric acid cycle and is used as a rodenticide, similar to sodium fluoroacetate. It is the main ingredient in the rodenticide product Gliftor which was widely used in the former USSR and still approved in China.

<span class="mw-page-title-main">Fluoroacetyl chloride</span> Chemical compound

Fluoroacetyl chloride is an acyl chloride.

<span class="mw-page-title-main">Methyl fluoroacetate</span> Chemical compound

Methyl fluoroacetate (MFA) is an organic compound with the chemical formula FCH2CO2CH3. It is an extremely toxic methyl ester of fluoroacetic acid. It is a colorless, odorless liquid at room temperature. It is used as a laboratory chemical and as a rodenticide. Because of its extreme toxicity, MFA was studied for potential use as a chemical weapon.

<span class="mw-page-title-main">Fluoroethyl fluoroacetate</span> Chemical compound

Fluoroethyl fluoroacetate, or more accurately 2-fluoroethyl fluoroacetate, is an organic compound with the chemical formula FCH2CO2CH2CH2F. It is the fluoroacetate ester of 2-fluoroethanol, or in other words, the 2-fluoroethyl ester of fluoroacetic acid. 2-Fluoroethyl fluoroacetate is two times more toxic than methyl fluoroacetate.

<span class="mw-page-title-main">Citrate–malate shuttle</span> Series of chemical reactions

The citrate-malate shuttle is a series of chemical reactions, commonly referred to as a biochemical cycle or system, that transports acetyl-CoA in the mitochondrial matrix across the inner and outer mitochondrial membranes for fatty acid synthesis. Mitochondria are enclosed in a double membrane. As the inner mitochondrial membrane is impermeable to acetyl-CoA, the shuttle system is essential to fatty acid synthesis in the cytosol. It plays an important role in the generation of lipids in the liver.

<span class="mw-page-title-main">2-Ethylhexyl fluoroacetate</span> Chemical compound

2-Ethylhexyl fluoroacetate is an organic compound with the chemical formula FCH2CO2CH2CH(CH2CH3)CH2CH2CH2CH3. It is the fluoroacetate ester of 2-ethylhexanol, in other words, the 2-ethylhexyl ester of fluoroacetic acid. It can be produced by reaction of ethyl fluoroacetate with 2-ethylhexanol. 2-Ethylhexyl fluoroacetate is a liquid that is highly toxic by skin absorption.

References

  1. H., Garrett, Reginald (2013). Biochemistry. Grisham, Charles M. (5th ed.). Belmont, CA: Brooks/Cole, Cengage Learning. ISBN   9781133106296. OCLC   777722371.{{cite book}}: CS1 maint: multiple names: authors list (link)
  2. Horák, J.; Linhart, I.; Klusoň, P. (2004). Úvod do toxikologie a ekologie pro chemiky (in Czech) (1st ed.). Prague: VŠCHT v Praze. ISBN   80-7080-548-X.