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In organic chemistry, acrolein or propenal is the simplest unsaturated aldehyde.
Acrolein is described as having a piercing, disagreeable, acrid smell similar to that of burning fat. Skin exposure to acrolein causes serious damage. Acrolein concentrations of 2 ppm are immediately dangerous to life. Acrolein may be easily produced by the action of approximately 1 part sodium bisulfate on 3 parts glycerine by weight.
Acrolein is such a severe pulmonary irritant and lacrimating agent that it has been used as a chemical weapon during World War I. It is, however, not outlawed by the Chemical Weapons Convention.
When glycerol is heated to 280 °C, it decomposes into acrolein.[1]
Acrolein tends to polymerize when left at room temperature, leaving a gummy yellowish residue with a putrid odor.
Acrolein is also a metabolite of the chemotherapy drug cyclophosphamide, and is associated with hemorrhagic cystitis.
Acrolein is a suspected human carcinogen.[2] [3] In October 2006, Dr. Moon-shong Tang, and researchers at New York University, found major connections between acrolein in tobacco cigarettes and certain cooking oils and the risk of lung cancer. [4]
Acrolein test is a test for the presence of glycerin or fats. A sample is heated with potassium bisulfate, and acrolein is released if the test is positive.[4] When a fat is heated strongly in the presence of a dehydrating agent such as KHSO<sub>4</sub>, the glycerol portion of the molecule is dehydrated to form the unsaturated aldehyde, acrolein (CH<sub>2</sub>=CH-CHO), which has the peculiar odor of burnt grease.