Methoxyacetic acid is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula . It can be viewed as a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

in which a hydrogen atom of the

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated a ...

is replaced by a

methoxy group In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position a ...

. As indicated by the synonym methyl glycolic acid, and as the simplest ether carboxylic acid, methoxyacetic acid can be understood as a methyl ether of

glycolic acid Glycolic acid (or hydroxyacetic acid; chemical formula ) is a colorless, odorless and hygroscopic crystal, crystalline solid, highly solubility, soluble in water. It is used in various skin care, skin-care products. Glycolic acid is widespread in ...

Production

In principle the compound can be prepared by reaction of

sodium methoxide Sodium methoxide is the simplest sodium alkoxide. With the formula , it is a white solid, which is formed by the deprotonation of methanol. It is a widely used reagent in industry and the laboratory. It is also a dangerously caustic base. ...

with monochloroacetic acid. The industrial route involves the oxidation of

2-methoxyethanol 2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for the ...

with air or

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

in the presence of platinum catalysts. In both humans and animals, 2-methoxyacetic acid forms via the rapid oxidation of 2-methoxyethanol by the action of alcohol dehydrogenases.

Properties

Methoxyacetic acid is a colorless, viscous, and corrosive liquid with a pungent odor which, at 7 °C, freezes to a mass similar to glacial acetic acid. Due to the low solvation energy of its methoxy group, methoxyacetic acid, with a pKa value of 3.57, is more acidic than acetic acid (pKa 4.757) and

(pKa 3.832). Ultra-pure methoxyacetic acid (purity of 99.8%, freezing point of 8.4 °C) can be obtained via the multistep

crystallization Crystallization is a process that leads to solids with highly organized Atom, atoms or Molecule, molecules, i.e. a crystal. The ordered nature of a crystalline solid can be contrasted with amorphous solids in which atoms or molecules lack regu ...

of the raw distillate, which is free of acid contaminations.

Applications

Methoxyacetic acid is a precursor to two commercial

fungicide Fungicides are pesticides used to kill parasitic fungi or their spores. Fungi can cause serious damage in agriculture, resulting in losses of yield and quality. Fungicides are used both in agriculture and to fight fungal infections in animals, ...

s, oxadixyl and mefenoxam.

Former applications

Due to its reprotoxic properties, earlier consumer and industrial applications of methoxyacetic acid as a

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ...

biocide A biocide is defined in the European legislation as a chemical substance or microorganism intended to destroy, deter, render harmless, or exert a controlling effect on any harmful organism. The US Environmental Protection Agency (EPA) uses a sli ...

, or as a cleaner for the decalcification of surfaces are now obsolete. The same is true for substances such as the solvent 2-methoxyethanol or the

PVC Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons o ...

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticizer ...

bis(2-methoxyethyl) phthalate Bis(2-methoxyethyl) phthalate, also commonly di(2-methoxyethyl) phthalate (DMEP), is a phthalate ester baring 2-methoxyethanol groups. Historically it was used as a plasticizer in cellulose acetate In biochemistry, cellulose acetate refers to ...

, which are metabolized to methoxyacetic acid.

Safety

Due to its considerable reprotoxic potential, methoxyacetic acid has been adopted into the list of SVHC substances (substances of very high concern) and is only registered as an intermediate product for industrial purposes under strictly controlled conditions. In laboratory tests, methoxyacetic acid inhibits the growth of tumor cells.

References

{{Reflist Methoxy compounds Carboxylic acids