Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C9H16O2 |
| Molecular Weight | 156.2221 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCC(O)\C=C\C=O
InChI
InChIKey=JVJFIQYAHPMBBX-FNORWQNLSA-N
InChI=1S/C9H16O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-9,11H,2-4,6H2,1H3/b7-5+
| Molecular Formula | C9H16O2 |
| Molecular Weight | 156.2221 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Optical Activity | ( + / - ) |
4-hydroxy-2-nonenal (4-HNE or HNE), a very reactive aldehyde derived from lipid peroxidation, is the product and mediator of oxidative stress. It can modulate a number of signaling processes mainly through forming covalent adducts with nucleophilic functional groups in proteins, nucleic acids, and membrane lipids. HNE is mutagenic and genotoxic because it reacts with all four DNA bases but with different efficiency: G >C > A >T. In addition, in the experiments with dogs was shown the pathophysiologic role of HNE in osteoarthritis.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Catabolism of 4-hydroxy-2-trans-nonenal by THP1 monocytes/macrophages and inactivation of carboxylesterases by this lipid electrophile. | 2011-10-15 |
|
| Cytochromes P450 catalyze the reduction of α,β-unsaturated aldehydes. | 2011-08-15 |
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| Protein-selective capture to analyze electrophile adduction of hsp90 by 4-hydroxynonenal. | 2011-08-15 |
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| Transient receptor potential ankyrin 1 is expressed by inhibitory motoneurons of the mouse intestine. | 2011-08 |
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| Aldehyde dehydrogenase 7A1 (ALDH7A1) attenuates reactive aldehyde and oxidative stress induced cytotoxicity. | 2011-05-30 |
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| Human aldo-keto reductases 1B1 and 1B10: a comparative study on their enzyme activity toward electrophilic carbonyl compounds. | 2011-05-30 |
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| Bioinformatic and biochemical characterization of DCXR and DHRS2/4 from Caenorhabditis elegans. | 2011-05-30 |
|
| Murine hepatic aldehyde dehydrogenase 1a1 is a major contributor to oxidation of aldehydes formed by lipid peroxidation. | 2011-05-30 |
|
| Protective effect of rat aldo-keto reductase (AKR1C15) on endothelial cell damage elicited by 4-hydroxy-2-nonenal. | 2011-05-30 |
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| The Drosophila carbonyl reductase sniffer is an efficient 4-oxonon-2-enal (4ONE) reductase. | 2011-05-30 |
|
| 4-Hydroxynonenal inhibits SIRT3 via thiol-specific modification. | 2011-05-16 |
|
| The effect of lipid peroxidation products on reactive oxygen species formation and nitric oxide production in lipopolysaccharide-stimulated RAW 264.7 macrophages. | 2011-02 |
|
| Teratogen-induced oxidative stress targets glyceraldehyde-3-phosphate dehydrogenase in the organogenesis stage mouse embryo. | 2010-12 |
|
| Mass spectrometric characterization of modifications to angiotensin II by lipid peroxidation products, 4-oxo-2(E)-nonenal and 4-hydroxy-2(E)-nonenal. | 2010-11-15 |
|
| Molecular characterization, expression analysis, and role of ALDH3B1 in the cellular protection against oxidative stress. | 2010-11-15 |
|
| Activation of metallothionein transcription by 4-hydroxynonenal. | 2010-10-28 |
|
| Quantitative structure-activity relationship for 4-hydroxy-2-alkenal induced cytotoxicity in L6 muscle cells. | 2010-10-06 |
|
| Oxidative stress induction by nanoparticles in THP-1 cells with 4-HNE production: stress biomarker or oxidative stress signalling molecule? | 2010-09 |
|
| NGF induced differentiated PC12 cells as in vitro tool to study 4-hydroxynonenal induced cellular damage. | 2010-09 |
|
| Carvedilol treatment ameliorates acute coxsackievirus B3-induced myocarditis associated with oxidative stress reduction. | 2010-08-25 |
|
| Transcriptional regulation of UCP4 by NF-kappaB and its role in mediating protection against MPP+ toxicity. | 2010-07-15 |
|
| Exposure to chrysotile asbestos causes carbonylation of glucose 6-phosphate dehydrogenase through a reaction with lipid peroxidation products in human lung epithelial cells. | 2010-05-19 |
|
| Reduced cellular redox status induces 4-hydroxynonenal-mediated caspase 3 activation leading to erythrocyte death during chronic arsenic exposure in rats. | 2010-05-01 |
|
| 4-Hydroxynonenal enhances MMP-9 production in murine macrophages via 5-lipoxygenase-mediated activation of ERK and p38 MAPK. | 2010-01-15 |
|
| Site-specific protein adducts of 4-hydroxy-2(E)-nonenal in human THP-1 monocytic cells: protein carbonylation is diminished by ascorbic acid. | 2010-01 |
|
| Disruption of the mGsta4 gene increases life span of C57BL mice. | 2010-01 |
|
| Alteration of Toll-like receptor 4 activation by 4-hydroxy-2-nonenal mediated by the suppression of receptor homodimerization. | 2009-11-10 |
|
| Protective role of glutathione S-transferase A4 induced in copper/zinc-superoxide dismutase knockout mice. | 2009-09-01 |
|
| Inhibition of NADPH oxidase is neuroprotective after ischemia-reperfusion. | 2009-07 |
|
| Proteomic identification of HNE-bound proteins in early Alzheimer disease: Insights into the role of lipid peroxidation in the progression of AD. | 2009-06-05 |
|
| Ascorbic acid promotes detoxification and elimination of 4-hydroxy-2(E)-nonenal in human monocytic THP-1 cells. | 2009-05 |
|
| Resveratrol prevents the prohypertrophic effects of oxidative stress on LKB1. | 2009-03-31 |
|
| Comparative analysis of gene expression changes mediated by individual constituents of hemozoin. | 2009-03-16 |
|
| Aldose reductase decreases endoplasmic reticulum stress in ischemic hearts. | 2009-03-16 |
|
| Role of human aldo-keto-reductase AKR1B10 in the protection against toxic aldehydes. | 2009-03-16 |
|
| Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress. | 2009-03-16 |
|
| 4-Hydroxynonenal enhances MMP-2 production in vascular smooth muscle cells via mitochondrial ROS-mediated activation of the Akt/NF-kappaB signaling pathways. | 2008-11-15 |
|
| Identification of proteins adducted by lipid peroxidation products in plasma and modifications of apolipoprotein A1 with a novel biotinylated phospholipid probe. | 2008-10 |
|
| Lipid peroxidation-derived aldehyde-protein adducts contribute to trichloroethene-mediated autoimmunity via activation of CD4+ T cells. | 2008-04-01 |
|
| Identification of protein targets of 4-hydroxynonenal using click chemistry for ex vivo biotinylation of azido and alkynyl derivatives. | 2008-02 |
|
| Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-beta peptide. | 2007-12-01 |
|
| Reactive aldehyde modification of thioredoxin-1 activates early steps of inflammation and cell adhesion. | 2007-11 |
|
| 4-Hydroxy-2-nonenal increases superoxide anion radical in endothelial cells via stimulated GTP cyclohydrolase proteasomal degradation. | 2007-11 |
|
| An ion channel essential for sensing chemical damage. | 2007-10-17 |
|
| An angiotensin II type-I receptor blocker, olmesartan medoxomil, attenuates lipid peroxidation in renal injury induced by subtotal nephrectomy. | 2007-09 |
|
| 4-Hydroxynonenal, an endogenous aldehyde, causes pain and neurogenic inflammation through activation of the irritant receptor TRPA1. | 2007-08-14 |
|
| Purification and cloning of a Delta class glutathione S-transferase displaying high peroxidase activity isolated from the German cockroach Blattella germanica. | 2007-04 |
|
| Actin Cys374 as a nucleophilic target of alpha,beta-unsaturated aldehydes. | 2007-03-01 |
|
| Lipid oxidation products and oxidized low-density lipoproteins impair platelet-derived growth factor receptor activity in smooth muscle cells: implication in atherosclerosis. | 2007 |
|
| Apoptosis signalling by 4-hydroxynonenal: a role for JNK-c-Jun/AP-1 pathway. | 2007 |
Sample Use Guides
In the second experimental protocol, a pathophysiologic dose of HNE (80 nmoles/ml) or vehicle was injected weekly into the right knee joints of crossbred dogs (n = 6 per group) for 8 weeks.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:57:13 GMT 2025
by
admin
on
Mon Mar 31 21:57:13 GMT 2025
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| Record UNII |
K1CVM13F96
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| Record Status |
Validated (UNII)
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| Record Version |
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29343-52-0
Created by
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K1CVM13F96
Created by
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m6034
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18286-49-2
Created by
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5283344
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4-Hydroxy-2-nonenal
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32585
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58968
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DTXSID4040395
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75899-68-2
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