Propanedial
[CAS# 542-78-9]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: Propanedial
• Synonyms: Malondialdehyde
• Molecular Formula: C₃H₄O₂
• Molecular Weight: 72.06
• CAS Registry Number: 542-78-9
• SMILES: C(C=O)C=O

Properties

• Density: 1.0±0.1 g/cm³, Calc.^*
• Melting point: 72 ºC
• Index of Refraction: 1.367, Calc.^*
• Boiling Point: 108.3±23.0 ºC (760 mmHg), Calc.^*
• Flash Point: 28.9±19.6 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02 Danger
• Hazard Statements: H225
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
• Transport Information: UN 1993

Discovory and Applicatios

Propanedial, also known as malondialdehyde (MDA), is a simple dialdehyde with the formula CH₂(CHO)₂. Its discovery and study stem from its role as a reactive metabolite and biomarker of oxidative stress in biological systems. First identified as a product of lipid peroxidation, propanedial was recognized for its significant biological implications, as it is formed when polyunsaturated fatty acids undergo oxidation. This compound’s discovery in cellular processes has led to extensive research on its applications in biochemical studies and diagnostics.

Propanedial’s structure, with two aldehyde groups attached to a central carbon, makes it highly reactive and able to readily form cross-links with proteins, nucleic acids, and other biomolecules. This reactivity allows it to be detected as a biomarker of oxidative damage in cells and tissues. In medical research, malondialdehyde levels in the body serve as an indicator of oxidative stress, which is associated with various health conditions, including cardiovascular diseases, neurodegenerative disorders, and inflammatory diseases. Testing for propanedial concentrations in blood, urine, or tissues is a common method to assess cellular damage due to oxidative stress, providing insights into disease progression and the effects of antioxidant treatments.

In analytical chemistry, propanedial is used in colorimetric assays due to its reactivity with thiobarbituric acid (TBA). The resulting malondialdehyde-TBA complex, which produces a pink color, is quantitatively measured in the thiobarbituric acid reactive substances (TBARS) assay. This assay is widely applied in food chemistry to evaluate lipid oxidation in food products, where MDA is used as a quality indicator for rancidity in fats and oils. In addition, this method is used in biological studies to measure lipid peroxidation in animal and plant tissues, further illustrating the role of propanedial in oxidative stress.

The applications of propanedial extend to industrial processes, where it is used as an intermediate in organic synthesis. Its reactivity with amines, thiols, and other nucleophiles makes it valuable in producing cross-linked materials, polymers, and certain pharmaceutical intermediates. Due to its toxicity and reactivity, handling propanedial requires caution, and ongoing research is focused on developing safer derivatives for industrial applications.

Propanedial’s discovery and continued research underscore its importance as a biomarker of oxidative stress and a valuable reagent in chemistry and diagnostics. Its diverse applications, from health assessments to industrial synthesis, highlight its role in advancing both scientific understanding and practical technologies.