 | |
| Names | |
|---|---|
| IUPAC name 2-Methoxyacetic acid | |
| Other names 2-Methoxyacetic acid Methyl glycolic acid | |
| Identifiers | |
| |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.009.904 |
| EC Number |
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| UNII | |
| Properties | |
| C3H6O3 | |
| Molar mass | 90.08 g/mol−1 |
| Appearance | Clear, colorless, viscous liquid with a pungent odor |
| Density | 1.1768 g/cm−3 |
| Melting point | 7–9 °C (45–48 °F; 280–282 K) |
| Boiling point | 202–204 °C (396–399 °F; 475–477 K) |
| Soluble in water, ethanol, and diethyl ether | |
| Vapor pressure | 1.8 mbar (20 °C) 4.8 mbar (50 °C) |
| Acidity (pKa) | 3.57 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Methoxyaceticacid is theorganic compound with the formulaCH3OCH2CO2H. It can be viewed as aderivative ofacetic acid in which a hydrogen atom of themethyl group is replaced by amethoxy group. As indicated by the synonym methyl glycolic acid, and as the simplest ether carboxylic acid, methoxyacetic acid can be understood as a methyl ether ofglycolic acid.
In principle the compound can be prepared by reaction ofsodium methoxide withmonochloroacetic acid. The industrial route involves the oxidation of2-methoxyethanol with air oroxygen in the presence of platinum catalysts.[1]
In both humans and animals, 2-methoxyacetic acid forms via the rapid oxidation of 2-methoxyethanol[2] by the action ofalcohol dehydrogenases.
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) andglycolic acid (pKa 3.832).[3]
Ultra-pure methoxyacetic acid (purity of 99.8%, freezing point of 8.4 °C) can be obtained via the multistepcrystallization of the raw distillate, which is free of acid contaminations.[4]
Methoxyacetic acid is a precursor to two commercialfungicides,oxadixyl andmefenoxam.
Due to its reprotoxic properties, earlier consumer and industrial applications of methoxyacetic acid as adisinfectant,biocide, 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 thePVCplasticizerbis(2-methoxyethyl) phthalate, which are metabolized to methoxyacetic acid.
Due to its considerablereprotoxic potential, methoxyacetic acid has been adopted into the list ofSVHC substances (substances of very high concern)[5] 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.[6]
