Structure via PubChem · Public domain (PubChem)
4-hydroxy-2-nonenal
Sign in to saveAlso known as 4-HNE, HNE, (E)-4-hydroxy-2-nonenal, trans-4-Hydroxy-2-nonenal, 4-Hydroxy-2,3-trans-nonenal, 4-hydroxynonenal, 4-Hydroxynon-2-enal, 4-Hydroxy-2,3-nonenal
4-Hydroxynonenal, or 4-hydroxy-2E-nonenal or 4-hydroxy-2-nonenal or 4-HNE or HNE, (''''''), is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular
Chemical data
- Formula
- C9H16O2
- Molecular weight
- 156.22 g/mol
- IUPAC name
- (E)-4-hydroxynon-2-enal
- SMILES
- CCCCCC(/C=C/C=O)O
- InChIKey
- JVJFIQYAHPMBBX-FNORWQNLSA-N
- XLogP
- 1.7
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- fatty aldehyde
- Mass
- 156.11503
Show 4 more facts
- chemical formula
- C₉H₁₆O₂
- isomeric SMILES
- CCCCCC(/C=C/C=O)O
- canonical SMILES
- CCCCCC(C=CC=O)O
- Commons category
- 4-Hydroxynonenal
via Wikidata · CC0
~7 min read
Encyclopedic overview
6 sectionsContents
- Synthesis
- Protein adducts
- Pathology
- Detoxification and related reactions
- Export
- References
4-Hydroxynonenal, or 4-hydroxy-2E-nonenal or 4-hydroxy-2-nonenal or 4-HNE or HNE, (''''), is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.
Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al., who also obtained the same compound synthetically. The topic has since been often reviewed, and one source describes the compound as "the most studied LPO (lipid peroxidation) product with pleiotropic capabilities".
Excerpted from Wikipedia’s “4-hydroxy-2-nonenal” article, available under the CC BY-SA 4.0 licence.