Glyoxylic acid
[CAS# 298-12-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty acid
• Name: Glyoxylic acid
• Synonyms: Oxo-acetic acid
• Molecular Formula: C₂H₂O₃
• Molecular Weight: 74.04
• CAS Registry Number: 298-12-4
• EC Number: 206-058-5
• SMILES: C(=O)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*, 1.339 g/mL
• Melting point: -93 °C
• Index of Refraction: 1.403, Calc.^*, 1.414
• Boiling Point: 224.6±23.0 °C (760 mmHg), Calc.^*, 111 °C
• Flash Point: 103.9±19.1 °C, Calc.^*
• Water solubility: miscible

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H318-H317
• Safety Statements: P234-P261-P264+P265-P272-P280-P302+P352-P305+P354+P338-P317-P321-P333+P317-P362+P364-P390-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1C	H314
Germ cell mutagenicity	Muta.	2	H341

Discovery and Applications

Glyoxylic acid is a simple organic compound characterized by the molecular formula C2H2O3. It features a carboxylic acid group and an aldehyde group, making it a highly versatile intermediate in organic synthesis. The compound was first isolated in the early 19th century, and its discovery is attributed to the work of chemists exploring the oxidation of glycolic acid and other hydroxy acids. Glyoxylic acid was synthesized by the oxidation of ethylene glycol or by the hydrolysis of oxalic acid. Its unique structure and functional groups make it an essential building block in various chemical reactions.

The applications of glyoxylic acid are extensive, particularly in the fields of organic chemistry, pharmaceuticals, and agrochemicals. One of its primary uses is as a key intermediate in the synthesis of amino acids, particularly glycine, which is essential for protein synthesis in living organisms. Glyoxylic acid is also utilized in the production of various pharmaceuticals, including the synthesis of antihistamines and other biologically active compounds. Its reactive aldehyde group allows it to participate in condensation reactions and facilitate the formation of more complex molecular structures.

In the textile and dye industries, glyoxylic acid is employed as a reagent in the synthesis of dyes and pigments. It serves as a crosslinking agent in the preparation of resins, enhancing the durability and stability of textile materials. Additionally, glyoxylic acid is used in the production of certain polymers and plastics, where it contributes to the formulation of specialty coatings and adhesives.

Furthermore, glyoxylic acid is recognized for its role in the field of biochemistry. It is involved in several metabolic pathways and serves as an important intermediate in the biosynthesis of various natural compounds. For example, it is a precursor in the synthesis of flavonoids and other plant secondary metabolites, which are known for their antioxidant and anti-inflammatory properties.

The versatility of glyoxylic acid extends to its application in the development of novel materials. Researchers are exploring its potential in the creation of bio-based materials, emphasizing sustainable and environmentally friendly alternatives to conventional synthetic processes. The compound's reactivity and ability to form covalent bonds make it an attractive candidate for use in bioengineering and the design of functional materials.

Recent studies have also highlighted the potential of glyoxylic acid in the field of medicine. Research is being conducted to evaluate its anticancer properties and its role as a potential therapeutic agent in treating various diseases. The compound's ability to modulate biological pathways may provide insights into new treatment strategies for conditions such as cancer and metabolic disorders.

In summary, glyoxylic acid is a significant chemical compound with a rich history and a wide range of applications. Its discovery laid the foundation for its use in organic synthesis, pharmaceuticals, and various industrial processes. Ongoing research continues to uncover new uses and properties of glyoxylic acid, solidifying its importance in both traditional and emerging fields of study.

References

2024. Hair-straightening cosmetics containing glyoxylic acid induce crystalline nephropathy. Kidney International, 106(6).
DOI: 10.1016/j.kint.2024.07.032

2024. Oxalate nephropathy associated with glyoxylate-containing hair-straightening products: a call for caution. Kidney International, 106(6).
DOI: 10.1016/j.kint.2024.09.015

2024. Extraction and mass transfer of glyoxylic acid in a capillary microchannel. Journal of Flow Chemistry, 14(4).
DOI: 10.1007/s41981-024-00340-1