4-Hydroxynonenal

4-Hydroxynonenal
Names
	Preferred IUPAC name 4-Hydroxynon-2-enal
	Other names 4-Hydroxy-2-nonenal
Identifiers
CAS Number	75899-68-2 (2E);
3D model (JSmol)	Interactive image;
Beilstein Reference	4660015 (2E,4R)
ChEBI	CHEBI:32585 ;
ChEMBL	ChEMBL454280 ;
ChemSpider	1630 (2Z) ; 4446465 (2E) ; 10131680 (2E,4R) ;
IUPHAR/BPS	6274;
MeSH	4-hydroxy-2-nonenal
PubChem CID	1693; 6433714 (2Z); 5283344 (2E); 11957428 (2E,4R);
UNII	K1CVM13F96 ;
CompTox Dashboard (EPA)	DTXSID4040395 ;
	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+ Key: JVJFIQYAHPMBBX-FNORWQNLSA-N ; 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	156.225 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). verify (what is ?) Infobox references

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.^[2]

Early identification and characterization of 4-hydroxynonenal was reported by Esterbauer, et al.,^[3] who also obtained the same compound synthetically.^[4] The topic has since been often reviewed,^[5] and one source describes the compound as "the most studied LPO (lipid peroxidation) product with pleiotropic capabilities".^[6]

^ "AC1L1C0X – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 13 October 2011.
^ Awasthi, Y. C.; Yang, Y.; Tiwari, N. K.; Patrick, B.; Sharma, A.; Li, J.; Awasthi, S. (2004). "Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases". Free Radical Biology and Medicine. 37 (5): 607–619. doi:10.1016/j.freeradbiomed.2004.05.033. PMID 15288119.
^ Benedetti, Angelo; Comporti, Mario; Esterbauer, Hermann (1980). "Identification of 4-Hydroxynonenal as a Cytotoxic Product Originating from the Peroxidation of Liver Microsomal Lipids". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 620 (2): 281–296. doi:10.1016/0005-2760(80)90209-X. PMID 6254573.
^ Esterbauer, H.; Weger, W. (1967). "Über die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 3. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, II". Monatshefte für Chemie. 98 (5): 1994–2000. doi:10.1007/BF01167162.
^ Ayala, Antonio; Muñoz, Mario F.; Argüelles, Sandro (2014). "Lipid Peroxidation: Production, Metabolism, and Signaling Mechanisms of Malondialdehyde and 4-Hydroxy-2-Nonenal". Oxidative Medicine and Cellular Longevity. 2014: 1–31. doi:10.1155/2014/360438. PMC 4066722. PMID 24999379.
^ Milkovic L, Zarkovic N, Marusic Z, Zarkovic K, Jaganjac M (March 29, 2023). "The 4-Hydroxynonel-Protein Adducts and Their Biological Relevance". Antioxidants (Review). 12 (4): 856. doi:10.3390/antiox12040856. PMC 10135105. PMID 37107229 – via MDPI.

[1] "AC1L1C0X – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 25 March 2005. Identification and Related Records. Retrieved 13 October 2011.

[2] Awasthi, Y. C.; Yang, Y.; Tiwari, N. K.; Patrick, B.; Sharma, A.; Li, J.; Awasthi, S. (2004). "Regulation of 4-hydroxynonenal-mediated signaling by glutathione S-transferases". Free Radical Biology and Medicine. 37 (5): 607–619. doi:10.1016/j.freeradbiomed.2004.05.033. PMID 15288119.

[3] Benedetti, Angelo; Comporti, Mario; Esterbauer, Hermann (1980). "Identification of 4-Hydroxynonenal as a Cytotoxic Product Originating from the Peroxidation of Liver Microsomal Lipids". Biochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism. 620 (2): 281–296. doi:10.1016/0005-2760(80)90209-X. PMID 6254573.

[4] Esterbauer, H.; Weger, W. (1967). "Über die Wirkungen von Aldehyden auf gesunde und maligne Zellen, 3. Mitt.: Synthese von homologen 4-Hydroxy-2-alkenalen, II". Monatshefte für Chemie. 98 (5): 1994–2000. doi:10.1007/BF01167162.

[5] Ayala, Antonio; Muñoz, Mario F.; Argüelles, Sandro (2014). "Lipid Peroxidation: Production, Metabolism, and Signaling Mechanisms of Malondialdehyde and 4-Hydroxy-2-Nonenal". Oxidative Medicine and Cellular Longevity. 2014: 1–31. doi:10.1155/2014/360438. PMC 4066722. PMID 24999379.

[:0-6] Milkovic L, Zarkovic N, Marusic Z, Zarkovic K, Jaganjac M (March 29, 2023). "The 4-Hydroxynonel-Protein Adducts and Their Biological Relevance". Antioxidants (Review). 12 (4): 856. doi:10.3390/antiox12040856. PMC 10135105. PMID 37107229 – via MDPI.

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