File:Acrolein-s-trans-2D-w.png · Wikimedia Commons · See Wikimedia Commons
acrolein
Sign in to saveAlso known as Slimicide, Crolean, Acquinite, trans-Acrolein Formylethylene, Propylene aldehyde, Propenaldehyde, Magnacide H, Allyl aldehyde
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as 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 propene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.
Chemical data
- Formula
- C3H4O
- Molecular weight
- 56.06 g/mol
- IUPAC name
- prop-2-enal
- SMILES
- C=CC=O
- InChIKey
- HGINCPLSRVDWNT-UHFFFAOYSA-N
- XLogP
- 0
- Polar surface area
- 17.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
6,230 papers- Acrolein: A Potential Mediator of Oxidative Damage in Diabetic Retinopathy.Biomolecules · 2020
- Acrolein: formation, health hazards and its controlling by dietary polyphenols.Critical reviews in food science and nutrition · 2024
- Acrolein toxicity at advanced age: present and future.Amino acids · 2018
- Acrolein.IARC monographs on the evaluation of carcinogenic risks to humans · 1995
- Acrolein health effects.Toxicology and industrial health · 2008
via PubMed
Wikidata facts
- Mass
- 56.026215
- Autonomy
- 234
Show 19 more facts
- lower flammable limit
- 2.8
- Commons category
- Acrolein
- vapor pressure
- 210
- canonical SMILES
- C=CC=O
- flash point
- -15
- chemical formula
- C₃H₄O
- solubility
- 40
- NIOSH Pocket Guide ID
- 0011
- density
- 1.9
- immediately dangerous to life or health
- 4.58
- melting point
- -87.7
- boiling point
- 52.69
- upper flammable limit
- 31
- ionization energy
- 10.10
- time-weighted average exposure limit
- 0.2
- short-term exposure limit
- 0.5
- minimal lethal dose
- 674
- median lethal dose (LD50)
- 375
- electric dipole moment
- 3.12
via Wikidata · CC0
~7 min read
Article
14 sectionsContents
- History
- Production
- Niche or laboratory methods
- Reactions
- Uses
- Military uses
- Biocide
- Chemical precursor
- Health risks
- Cigarette smoke
- Chemotherapy metabolite
- Endogenous production
- Analytical methods
- References
Acrolein (systematic name: propenal) is the simplest unsaturated aldehyde. It is a colorless liquid with a foul and acrid aroma. The smell of burnt fat (as 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 propene and mainly used as a biocide and a building block to other chemical compounds, such as the amino acid methionine.
==History== Acrolein was first named and characterized as an aldehyde by the Swedish chemist Jöns Jacob Berzelius in 1839. He had been working with it as a thermal degradation product of glycerol, a material used in the manufacture of soap. The name is a contraction of 'acrid' (referring to its pungent smell) and 'oleum' (referring to its oil-like consistency). In the 20th century, acrolein became an important intermediate for the industrial production of acrylic acid and acrylic plastics.