Glyoxylic acid monohydrate
[CAS# 563-96-2]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: Glyoxylic acid monohydrate
• Synonyms: Dihydroxyacetic acid; Formylformic acid; Oxoethanoic acid
• Molecular Formula: C₂H₄O₄
• Molecular Weight: 92.05
• CAS Registry Number: 563-96-2
• EC Number: 679-230-4
• SMILES: O.O=CC(=O)O

Properties

• Melting point: 49-52 °C (Expl.)
• Boiling point: 100 °C (Expl.)
• Flash point: >110 °C (Expl.)
• Water solubility: Freely soluble

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H290-H315-H317-H318
• Safety Statements: P234-P261-P264-P272-P280-P302+P352-P305+P351+P338+P310-P333+P313-P390-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1B	H317
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Respiratory sensitization	Resp. Sens.	1	H334

• Transport Information: UN 3261

Discovery and Applications

Glyoxylic acid monohydrate is a chemical compound that consists of glyoxylic acid and one molecule of water. Glyoxylic acid itself is a small organic acid with the formula C2H2O3, containing a formyl group (-CHO) and a carboxyl group (-COOH), making it an α-keto acid. It is a colorless, crystalline solid, and its monohydrate form is commonly encountered in chemical synthesis. Glyoxylic acid monohydrate is typically used as an intermediate in the production of various chemicals, and it plays a role in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

The discovery of glyoxylic acid can be traced back to the early 19th century. The compound has long been of interest due to its ability to participate in important chemical reactions such as aldol condensations, cyclization reactions, and as a precursor to other organic compounds. The monohydrate form of glyoxylic acid was later identified as a stable form of the compound, which makes it easier to handle and use in laboratory settings compared to the anhydrous form.

Glyoxylic acid monohydrate has several applications in chemical synthesis. One of its primary uses is as an intermediate in the production of α-hydroxy acids, which are important building blocks in the synthesis of pharmaceutical compounds. These α-hydroxy acids are used in the preparation of a variety of bioactive molecules, including antibiotics and anti-inflammatory agents. Glyoxylic acid is also involved in the preparation of compounds used in the production of flavors and fragrances.

Another important application of glyoxylic acid monohydrate is in the production of amino acids. It is commonly used in the synthesis of glycine, the simplest amino acid, through a reaction with ammonia or amines. Additionally, glyoxylic acid can be used in the synthesis of other organic molecules, including compounds used in agricultural chemicals.

In the field of materials science, glyoxylic acid derivatives have been studied for their potential use in polymerization reactions. Glyoxylic acid monohydrate and its derivatives can serve as monomers or crosslinking agents in the production of polymers with specific properties. This application is of interest for the development of advanced materials in coatings, adhesives, and other industrial products.

In summary, glyoxylic acid monohydrate is a well-established compound with a range of applications in chemical synthesis, particularly in the production of amino acids, pharmaceuticals, and agrochemicals. It is a valuable intermediate in the preparation of important organic compounds and continues to be a subject of research for various industrial applications.

References

2024. Glyoxylic acid monohydrate promoted reductive addition of sodium sulfinates to pillar[4]arene[1]quinone. Org. Biomol. Chem., 23(5).
DOI: 10.1039/D4OB01908C

2018. Decarboxylative formylation of aryl halides with glyoxylic acid by merging organophotoredox with palladium catalysis. Org. Chem. Front., 5(11).
DOI: 10.1039/C8QO00253C

2014. Catalyst-free soft-template synthesis of ordered mesoporous carbon tailored using phloroglucinol/glyoxylic acid environmentally friendly precursors. Green Chem., 16(6).
DOI: 10.1039/C4GC00269E