4-Hydroxynonenal

4-Hydroxynonenal

Names
Preferred IUPAC name 4-Hydroxy-2-nonenal
Systematic IUPAC name 4-Hydroxynon-2-enal
Identifiers
CAS Number	29343-52-0 N 18286-49-2 (2E) Y
3D model (Jmol)	Interactive image
Beilstein Reference	4660015 (2E,4R)
ChEBI	CHEBI:32585 N
ChEMBL	ChEMBL454280 Y
ChemSpider	1630 (2Z) N 4446465 (2E) Y 10131680 (2E,4R) Y
IUPHAR/BPS	6274
MeSH	4-hydroxy-2-nonenal
PubChem	1693 6433714 (2Z) 5283344 (2E) 11957428 (2E,4R)
InChI 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
SMILES CCCCCC(O)C=CC=O
Properties
Chemical formula	C9H16O2
Molar mass	156.23 g·mol−1
Density	0.944 g cm−3
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  (what is YN ?)
Infobox references

Malondialdehyde

4-Hydroxynonenal, 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 alpha,beta-unsaturated hydroxyalkenal formed in this process.

4-HNE has 3 reactive groups: an aldehyde, a double-bond at carbon 2, and a hydroxy group at carbon 4.

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.

The first characterization of 4-hydroxynonenal was reported by Esterbauer, et al. in 1991, and since then the amount of research involving this chemical has been steadily increasing, with entire issues of relatively high-impact journals such as Molecular Aspects of Medicine and Free Radical Biology and Medicine devoting volumes to 4-HNE-centered publications.

4-Hydroxynonenal is generated in the oxidation of lipids containing polyunsaturated omega-6 acyl groups, such as arachidonic or linoleic groups, and of the corresponding fatty acids viz., the hydroperoxy precursors to 15-hydroxyicosatetraenoic acid and 13-hydroxyoctadecadienoic acid, respectively. Although they are the most studied ones, in the same process other oxygenated α,β-unsaturated aldehydes (OαβUAs) are generated also, which can also come from omega-3 fatty acids, such as 4-oxo-trans-2-nonenal, 4-hydroxy-trans-2-hexenal, 4-hydroperoxy-trans-2-nonenal and 4,5-epoxy-trans-2-decenal.