4-Hydroxynonenal

4-Hydroxynonenal, or 4-hydroxy-2E-nonenal or 4-hydroxy-2-nonenal or 4-HNE or HNE, (C9H16O2), 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.

4-Hydroxynonenal
Names
Preferred IUPAC name
4-Hydroxynon-2-enal
Other names
4-Hydroxy-2-nonenal
Identifiers
3D model (JSmol)
4660015 (2E,4R)
ChEBI
ChEMBL
ChemSpider
MeSH 4-hydroxy-2-nonenal
UNII
  • InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+ Y
    Key: JVJFIQYAHPMBBX-FNORWQNLSA-N Y
  • InChI=1/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
    Key: JVJFIQYAHPMBBX-FNORWQNLBE
  • CCCCCC(O)C=CC=O
Properties
C9H16O2
Molar mass 156.225 g·mol−1
Density 0.944 g⋅cm−3
Boiling point 125–127 °C (257–261 °F; 398–400 K) 2 torr
log P 1.897
Acidity (pKa) 13.314
Basicity (pKb) 0.683
Related compounds
Related alkenals
 Glucic acid
Malondialdehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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".

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