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Carboxyacetic Acid, an analogue of the Krebs/citric acid cycle, serves as a marker for intestinal microbial overgrowth, particularly involving yeast and fungi.
As a byproduct of the Krebs cycle, elevated levels may also point to energy metabolism disorders.
Research has shown that children with autism tend to have lower levels of Carboxyacetic Acid, which is thought to result from increased uptake of these compounds across the blood-brain barrier.
CAS No: 64-19-7
Molecular Formula: CH3COOH
Molecular Weight: 60.05
Synonym(s): Dichlorothiophene Carboxylic Acid, (3,5-dichlorothiophene-2-carboxylic acid)
Urinary levels of Carboxyacetic Acid have been observed to decrease following nystatin therapy.
To identify the root cause, consider testing with a Gut Zoomer, fungal antibodies, or a mycotoxin panel.
Implementing multi-strain probiotics and comprehensive gastrointestinal support can help improve this condition.
In organic chemistry, a Carboxyacetic Acid is an organic acid that contains a carboxyl group (−C(=O)−OH) attached to an R-group.
The general formula of a Carboxyacetic Acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group (e.g., alkyl, alkenyl, aryl), or hydrogen, or other groups.
Carboxylic acids occur widely.
Important examples include the amino acids and fatty acids.
Deprotonation of a Carboxyacetic Acid gives a carboxylate anion.
Carboxylic acids are commonly identified by their trivial names.
They often have the suffix -ic acid.
IUPAC-recommended names also exist; in this system, carboxylic acids have an -oic acid suffix.
For example, butyric acid (CH3CH2CH2CO2H) is butanoic acid by IUPAC guidelines.
For nomenclature of complex molecules containing a carboxylic acid, the carboxyl can be considered position one of the parent chain even if there are other substituents, such as 3-chloropropanoic acid.
Alternately, Carboxyacetic Acid can be named as a "carboxy" or "carboxylic acid" substituent on another parent structure, such as 2-carboxyfuran.
The carboxylate anion (R−COO− or R−CO−2) of a carboxylic acid is usually named with the suffix -ate, in keeping with the general pattern of -ic acid and -ate for a conjugate acid and its conjugate base, respectively.
For example, the conjugate base of acetic acid is acetate.
Carbonic acid, which occurs in bicarbonate buffer systems in nature, is not generally classed as one of the carboxylic acids, despite Carboxyacetic Acid having a moiety that looks like a COOH group.
Carboxyacetic Acid is a fine chemical that is used in research, as well as in the synthesis of other compounds.
Carboxyacetic Acid is a versatile building block that can be used to make more complex compounds and has been shown to be useful in many reactions.
Carboxyacetic Acid is also a useful intermediate and scaffold for drug design and development.
Carboxyacetic Acid can be used to synthesize drugs that are capable of inhibiting protein translation or protein synthesis.
Physical properties
Solubility
Carboxylic acids are polar.
Because they are both hydrogen-bond acceptors (the carbonyl −C(=O)−) and hydrogen-bond donors (the hydroxyl −OH), they also participate in hydrogen bonding.
Together, the hydroxyl and carbonyl group form the functional group carboxyl.
Carboxylic acids usually exist as dimers in nonpolar media due to their tendency to "self-associate".
Smaller carboxylic acids (1 to 5 carbons) are soluble in water, whereas bigger carboxylic acids have limited solubility due to the increasing hydrophobic nature of the alkyl chain.
These longer chain acids tend to be soluble in less-polar solvents such as ethers and alcohols.
Aqueous sodium hydroxide and carboxylic acids, even hydrophobic ones, react to yield water-soluble sodium salts.
For example, enanthic acid has a low solubility in water (0.2 g/L), but its sodium salt is very soluble in water.
Boiling points
Carboxylic acids tend to have higher boiling points than water, because of their greater surface areas and their tendency to form stabilized dimers through hydrogen bonds.
For boiling to occur, either the dimer bonds must be broken or the entire dimer arrangement must be vaporized, increasing the enthalpy of vaporization requirements significantly.
Acidity
Carboxylic acids are Brønsted–Lowry acids because they are proton (H+) donors.
4They are the most common type of organic acid.
Carboxylic acids are typically weak acids, meaning that they only partially dissociate into [H3O]+ cations and R−CO−2 anions in neutral aqueous solution.
For example, at room temperature, in a 1-molar solution of acetic acid, only 0.001% of the acid are dissociated (i.e. 10−5 moles out of 1 mol).
Electron-withdrawing substituents such as trifluoromethyl (−CF3) give stronger acids (the pKa of acetic acid is 4.76 whereas trifluoroacetic acid, with a trifluoromethyl substituent, has a pKa of 0.23).
Electron-donating substituents give weaker acids (the pKa of formic acid is 3.75 whereas acetic acid, with a methyl substituent, has a pKa of 4.76)
