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Metabolite Card

Note

Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colourless liquid with a piercing, disagreeable, acrid smell. The smell of burnt fat (i.e. when cooking oil is heated to its smoke point) is caused by glycerol in the burning fat breaking down into acrolein. It is produced industrially from propylene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine. Acrolein is used as an etherification agent in the preparation of modified food starches. Acrolein is an herbicide and algicide used in water treatment. It is produced by microorganisms, e.g. Clostridium perfringens. Acrolein is a relatively electrophilic compound and a reactive one, hence its high toxicity. It is a good Michael acceptor, hence its useful reaction with thiols. It forms acetals readily, a prominent one being the spirocycle derived from pentaerythritol, diallylidene pentaerythritol. Acrolein participates in many Diels-Alder reactions, even with itself. Via Diels-Alder reactions, it is a precursor to some commercial fragrances, including lyral, norbornene-2-carboxaldehyde, and myrac aldehyde. Acrolein is toxic and is a strong irritant for the skin, eyes, and nasal passages. The main metabolic pathway for acrolein is the alkylation of glutathione. The WHO suggests a 'tolerable oral acrolein intake' of 7.5 µg/day per kilogram of body weight. Although acrolein occurs in French fries, the levels are only a few micrograms per kilogram. Acrolein has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821).