Editing 4-Hydroxynonenal (section)

{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477222328
| ImageFile = 4-hydroxynonenal-Line-Structure.png
| ImageSize = 250px
| ImageFile1 = 4-Hydroxynonenal 3D Balls.png
| ImageSize1 = 300px
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageName = Skeletal formula of 4-hydroxynonenal ((2E)-2-en)
| PIN = 4-Hydroxynon-2-enal<ref>{{cite web|title = AC1L1C0X – Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1693|work = PubChem Compound|publisher = National Center for Biotechnology Information|access-date = 13 October 2011|location = USA|date = 25 March 2005|at = Identification and Related Records}}</ref>
| OtherNames = 4-Hydroxy-2-nonenal
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 6274

| CASNo = 75899-68-2 
| CASNo_Comment = <small>(2''E'')</small>

| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = K1CVM13F96

| PubChem = 1693
| PubChem1 = 6433714
| PubChem1_Comment = <small>(2''Z'')</small>
| PubChem2 = 5283344
| PubChem2_Comment = <small>(2''E'')</small>
| PubChem3 = 11957428
| PubChem3_Comment = <small>(2''E'',4''R'')</small>
| ChemSpiderID = 1630
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID_Comment = <small>(2''Z'')</small>
| ChemSpiderID1 = 4446465
| ChemSpiderID1_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID1_Comment = <small>(2''E'')</small>
| ChemSpiderID2 = 10131680
| ChemSpiderID2_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID2_Comment = <small>(2''E'',4''R'')</small>
| MeSHName = 4-hydroxy-2-nonenal
| ChEBI = 32585
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 454280
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| Beilstein = 4660015 <small>(2''E'',4''R'')</small>
| SMILES = CCCCCC(O)C=CC=O
| StdInChI = 1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChI = 1/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
| StdInChIKey = JVJFIQYAHPMBBX-FNORWQNLSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = JVJFIQYAHPMBBX-FNORWQNLBE
}}
|Section2={{Chembox Properties
| C=9 | H=16 | O=2 
| Density = 0.944 g⋅cm<sup>−3</sup>
| BoilingPtC = 125-127
| BoilingPt_notes = 2 torr
| LogP = 1.897
| pKa = 13.314
| pKb = 0.683
}}
|Section3={{Chembox Related
| OtherFunction_label = alkenals
| OtherFunction = [[Glucic acid]]<br />[[Malondialdehyde]]
}}
}}

'''4-Hydroxynonenal''', or '''4-hydroxy-2E-nonenal''' or '''4-hydroxy-2-nonenal''' or '''4-HNE''' or '''HNE''', ('''{{chem2|C9H16O2|auto=1}}'''), 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.<ref>{{Cite journal | last1 = Awasthi | first1 = Y. C. | last2 = Yang | first2 = Y. | last3 = Tiwari | first3 = N. K. | last4 = Patrick | first4 = B. | last5 = Sharma | first5 = A. | last6 = Li | first6 = J. | last7 = Awasthi | first7 = S. | doi = 10.1016/j.freeradbiomed.2004.05.033 | title = Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases | journal = Free Radical Biology and Medicine | volume = 37 | issue = 5 | pages = 607–619 | year = 2004 | pmid =  15288119}}</ref>

Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al.,<ref>{{Cite journal  | doi =  10.1016/0005-2760(80)90209-X| title = Identification of 4-Hydroxynonenal as a Cytotoxic Product Originating from the Peroxidation of Liver Microsomal Lipids| year = 1980| last1 = Benedetti| first1 = Angelo| last2 = Comporti| first2 = Mario| last3 = Esterbauer| first3 = Hermann| journal = Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism| volume = 620| issue = 2| pages = 281–296| pmid = 6254573}}</ref> who also obtained the same compound synthetically.<ref>{{cite journal |doi=10.1007/BF01167162|title=Über die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 3. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, II |year=1967 |last1=Esterbauer |first1=H. |last2=Weger |first2=W. |journal=Monatshefte für Chemie |volume=98 |issue=5 |pages=1994–2000 }}</ref> The topic has since been often reviewed,<ref>{{cite journal |doi=10.1155/2014/360438|doi-access=free |title=Lipid Peroxidation: Production, Metabolism, and Signaling Mechanisms of Malondialdehyde and 4-Hydroxy-2-Nonenal |year=2014 |last1=Ayala |first1=Antonio |last2=Muñoz |first2=Mario F. |last3=Argüelles |first3=Sandro |journal=Oxidative Medicine and Cellular Longevity |volume=2014 |pages=1–31 |pmid=24999379 |pmc=4066722 }}</ref> and one source describes the compound as "the most studied LPO (lipid peroxidation) product with pleiotropic capabilities".<ref name=":0">{{Cite journal |vauthors=Milkovic L, Zarkovic N, Marusic Z, Zarkovic K, Jaganjac M |date=March 29, 2023<!--acceptance date by journal--> |title=The 4-Hydroxynonel-Protein Adducts and Their Biological Relevance |url=https://www.mdpi.com/2076-3921/12/4/856/pdf?version=1680342805 |journal=[[Antioxidants (journal)|Antioxidants]] |type=Review |volume=12 |issue=4 |pages=856 |doi=10.3390/antiox12040856 |pmc=10135105 |pmid=37107229 |via=MDPI |doi-access=free }}</ref>