What Is Glyoxylate?
Glyoxylate is a carboxylic acid with the molecular formula C2H2O3.
Its IUPAC nomenclature is oxoethanoic acid, and its CAS number is 298-12-4.
It has a molecular weight of 74.04, a melting point of -93°C, a boiling point of 111°C, and is a colorless, odorless solid at room temperature.
Uses of Glyoxylate
Glyoxylate has uses as a pharmaceutical and fragrance ingredient. In food additives and cosmetics, it is often used as a pH adjuster.
It is also a substance used as a reagent in the Hopkins-Cole reaction, a tryptophan-detecting reaction in biochemistry. In some plants and fungi, it is used in a metabolic pathway called the glyoxylate circuit to combine with acetyl CoA to synthesize malic acid.
An application that has been gaining attention in recent years is the treatment effect of glyoxylate on hair. By attaching a treatment solution with glyoxylate as its main ingredient to the hair and applying heat, it is said that the dryness and distortion of the hair can be suppressed.
Characteristics of Glyoxylate
The aldehyde group of glyoxylate is generally in a structure in which the hydrate is actually hydrated or the hydrate further forms a dimer. Note that when isolated, the hydrogen atom of the carboxyl group forms a cyclic hydrogen bond with the oxygen atom of the aldehyde group.
Glyoxylate is a substance that exhibits acidity about 10 times stronger than that of acetic acid. It is also disproportionate in the presence of a base to produce glycolic acid and hydroxyl acid. It is nonflammable, but when heated, it is unstable and decomposes on heating, producing formic aldehyde.
Types of Glyoxylate
Glyoxylate is sold primarily as an R&D reagent and as a chemical in the chemical industry. In R&D reagents, glyoxylic acid is available as monohydrate or 50% aqueous solution.
Monohydrate is available in 10 g, 25 g, 10 g, 500 g, and other types of volumes. It is available in packaging such as polyethylene bottles that are easy to handle in the laboratory. It can be stored at room temperature, but is sometimes treated as a reagent requiring storage at 25°C or lower.
As a chemical for the chemical industry, it is sold mainly as a 50% aqueous solution. To meet the needs of factories, etc., these chemicals are available in large capacities, such as 25 kg, and in packaging such as polyethylene cans.
Other Information on Glyoxylate
1. Synthesis of Glyoxylate
Glyoxylate can be synthesized by electrolysis of oxalic acid with lead dioxide. Ozone oxidation of maleic acid is also considered an effective method.
2. Chemical Reaction of Glyoxylate
Glyoxylate is a compound used in the synthesis of various useful chemicals because of its electrophilic substitution reaction with phenols.
The addition of glyoxylate to guaiacol, followed by oxidation and decarboxylation, is also used in the synthesis of vanillin. Vanillin is the main substance responsible for the aroma of vanilla.
Glyoxylate is an intermediate in the metabolism of ethylene glycol to oxalic acid in humans.