glycolaldehyde

Glycolaldehyde, also known as 2-hydroxyacetaldehyde, is the simplest sugar-related aldehyde, with chemical formula C2H4O2. Its structure consists of a two-carbon chain bearing an aldehyde group at one end and a hydroxymethyl group at the other (HO-CH2-CHO). It is typically a colorless liquid at room temperature and is soluble in water. In aqueous solution, glycolaldehyde readily forms a geminal diol hydrate.

Glycolaldehyde occupies a central role in prebiotic chemistry as a key intermediate in aldol-type reactions that build larger carbohydrates from simple starting materials. In the formose reaction, under basic conditions, glycolaldehyde can react with formaldehyde and other small carbonyl compounds to generate a family of sugars, including glyceraldehyde and ribose-like molecules. This potential pathway to sugars has made glycolaldehyde a focal point in studies of the chemical origins of life.

Natural occurrence and astrochemical significance: Glycolaldehyde has been detected in interstellar environments, including molecular clouds and star-forming regions, and has been found in carbonaceous meteorites. Observations indicate it can be produced by photochemical processing in icy grains or during stellar processes, supporting its relevance to extraterrestrial organic chemistry.

Synthesis, uses, and safety: In laboratory research, glycolaldehyde is prepared and handled as a reactive aldehyde and serves as a building block for studies of carbohydrate chemistry and prebiotic models. It readily participates in aldol reactions and related condensations. Safety concerns include its irritant and reactive nature; it is flammable and should be handled with appropriate precautions to avoid inhalation, ingestion, or contact with skin and eyes.