4-hydroxyhexenal
hexenal, 4-hydroxy-
 
Notes:
metabolite from senecionine.
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CAS Number: 17427-08-6Picture of molecule3D/inchi
Nikkaji Web: J49.434H
XlogP3-AA: 0.20 (est)
Molecular Weight: 114.14410000
Formula: C6 H10 O2
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 233.00 to  234.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.010000 mmHg @ 25.00 °C. (est)
Flash Point: 203.00 °F. TCC ( 94.90 °C. ) (est)
logP (o/w): 0.368 (est)
Soluble in:
 water, 3.118e+005 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50  110 mg/kg
Personal Communication from H. Zollner, Institut fur Biochemie, Der Universitat, Gras, Oct. 23, 1975Vol. 23OCT1975

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for 4-hydroxyhexenal usage levels up to:
 not for fragrance use.
 
Recommendation for 4-hydroxyhexenal flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5283314
National Institute of Allergy and Infectious Diseases: Data
 (E)-4-hydroxyhex-2-enal
Chemidplus: 0017427086
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References:
 (E)-4-hydroxyhex-2-enal
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5283314
Pubchem (sid): 134992329
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 hexenal, 4-hydroxy-
2-hexenal, 4-hydroxy-, (2E)-
2-hexenal, 4-hydroxy-, (E)-
(2E)-4-hydroxy-2-hexenal
(E)-4-hydroxy-2-hexenal
4-hydroxy-2-hexenal
trans-4-hydroxy-2-hexenal
(2E)-4-hydroxyhex-2-enal
(E)-4-hydroxyhex-2-enal
(E)-4-hydroxyhexenal
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Articles:
PubMed: Omega-3 fatty acids protect the brain against ischemic injury by activating Nrf2 and upregulating heme oxygenase 1.
PubMed: Noninvasive detection of lung cancer using exhaled breath.
PubMed: Accumulation of hydroxyl lipids and 4-hydroxy-2-hexenal in live fish infected with fish diseases.
PubMed: 4-Hydroxy hexenal derived from dietary n-3 polyunsaturated fatty acids induces anti-oxidative enzyme heme oxygenase-1 in multiple organs.
PubMed: Correction: Paricalcitol Attenuates 4-Hydroxy-2-Hexenal-Induced Inflammation and Epithelial-Mesenchymal Transition in Human Renal Proximal Tubular Epithelial Cells.
PubMed: Re-assessing the mechanism of action of n-3 PUFAs.
PubMed: 4-Hydroxy hexenal derived from docosahexaenoic acid protects endothelial cells via Nrf2 activation.
PubMed: Dietary strategy to repair plasma membrane after brain trauma: implications for plasticity and cognition.
PubMed: Exercise facilitates the action of dietary DHA on functional recovery after brain trauma.
PubMed: Lipoxidation adducts with peptides and proteins: deleterious modifications or signaling mechanisms?
PubMed: 4-hydroxyhexenal- and 4-hydroxynonenal-modified proteins in pterygia.
PubMed: High-fat diet induces changes in adipose tissue trans-4-oxo-2-nonenal and trans-4-hydroxy-2-nonenal levels in a depot-specific manner.
PubMed: Paricalcitol attenuates 4-hydroxy-2-hexenal-induced inflammation and epithelial-mesenchymal transition in human renal proximal tubular epithelial cells.
PubMed: The omega-3 fatty acid eicosapentaenoic acid accelerates disease progression in a model of amyotrophic lateral sclerosis.
PubMed: Dietary carnosine prevents early atherosclerotic lesion formation in apolipoprotein E-null mice.
PubMed: Mutagenic/recombinogenic effects of four lipid peroxidation products in Drosophila.
PubMed: Dietary oxidized n-3 PUFA induce oxidative stress and inflammation: role of intestinal absorption of 4-HHE and reactivity in intestinal cells.
PubMed: A comparative 'bottom up' proteomics strategy for the site-specific identification and quantification of protein modifications by electrophilic lipids.
PubMed: 4-Hydroxyhexenal (HHE) impairs glutamate transport in astrocyte cultures.
PubMed: Oxidised fish oil does not influence established markers of oxidative stress in healthy human subjects: a randomised controlled trial.
PubMed: Increasing intake of long-chain n-3 PUFA enhances lipoperoxidation and modulates hepatic gene expression in a dose-dependent manner.
PubMed: Immunohistochemical detection of polyunsaturated fatty acid oxidation markers in acetaminophen-induced liver injury in rats.
PubMed: Aldehyde stress and up-regulation of Nrf2-mediated antioxidant systems accompany functional adaptations in cardiac mitochondria from mice fed n-3 polyunsaturated fatty acids.
PubMed: Cholesterol secosterol aldehydes induce amyloidogenesis and dysfunction of wild-type tumor protein p53.
PubMed: 4-Hydroxy-2-hexenal-induced apoptosis in human renal proximal tubular epithelial cells.
PubMed: Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay.
PubMed: Site-specific proteomic analysis of lipoxidation adducts in cardiac mitochondria reveals chemical diversity of 2-alkenal adduction.
PubMed: Structural and functional changes in human insulin induced by the lipid peroxidation byproducts 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal.
PubMed: Effect of reactive oxygen and carbonyl species on crucial cellular antioxidant enzymes.
PubMed: Evidence supporting a role for N-(3-formyl-3,4-dehydropiperidino)lysine accumulation in Müller glia dysfunction and death in diabetic retinopathy.
PubMed: Elevated 4-hydroxyhexenal in Alzheimer's disease (AD) progression.
PubMed: Fate in digestion in vitro of several food components, including some toxic compounds coming from omega-3 and omega-6 lipids.
PubMed: Low concentration of 4-hydroxy hexenal increases heme oxygenase-1 expression through activation of Nrf2 and antioxidative activity in vascular endothelial cells.
PubMed: Kinetic and structural evidence of the alkenal/one reductase specificity of human ζ-crystallin.
PubMed: Properties and tissue distribution of a novel aldo-keto reductase encoding in a rat gene (Akr1b10).
PubMed: Quantitative structure-activity relationship for 4-hydroxy-2-alkenal induced cytotoxicity in L6 muscle cells.
PubMed: Trans-4-hydroxy-2-hexenal, a product of n-3 fatty acid peroxidation: make some room HNE...
PubMed: Ethanol withdrawal increases glutathione adducts of 4-hydroxy-2-hexenal but not 4-hydroxyl-2-nonenal in the rat cerebral cortex.
PubMed: Effects of Lipid Peroxidation-Derived Products on the Growth of Human Colorectal Cancer Cell Line HT-29.
PubMed: Transgenic expression of proximal tubule peroxisome proliferator-activated receptor-alpha in mice confers protection during acute kidney injury.
PubMed: High levels of retinal membrane docosahexaenoic acid increase susceptibility to stress-induced degeneration.
PubMed: Lipid peroxidation of membrane phospholipids generates hydroxy-alkenals and oxidized phospholipids active in physiological and/or pathological conditions.
PubMed: Oxidation products of polyunsaturated fatty acids in infant formulas compared to human milk--a preliminary study.
PubMed: The effects of NaCl on lipid peroxidation-derived aldehyde, 4-hydroxy-2-hexenal formation in boiled yellowtail meat.
PubMed: Immunohistochemical analysis of aldehyde-modified proteins in drusen in cynomolgus monkeys (Macaca fascicularis).
PubMed: Increased susceptibility to oxidant-mediated tissue injury and peritoneal fibrosis in acatalasemic mice.
PubMed: Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress.
PubMed: Trans-4-hydroxy-2-hexenal is a neurotoxic product of docosahexaenoic (22:6; n-3) acid oxidation.
PubMed: Aberrant expression of selenoproteins in the progression of colorectal cancer.
PubMed: 4-hydroxy-2-alkenals in polyunsaturated fatty acids-fortified infant formulas and other commercial food products.
PubMed: Formaldehyde-protein conjugate-specific antibodies in rats exposed to formaldehyde.
PubMed: Protective effect of TEMPOL derivatives against light-induced retinal damage in rats.
PubMed: Design, synthesis, and application of a hydrazide-functionalized isotope-coded affinity tag for the quantification of oxylipid-protein conjugates.
PubMed: Effects of NaCl on 4-hydroxy-2-hexenal formation in yellowtail meat stored at 0 degrees C.
PubMed: Hydroxy-alkenals from the peroxidation of n-3 and n-6 fatty acids and urinary metabolites.
PubMed: Attenuation of folic acid-induced renal inflammatory injury in platelet-activating factor receptor-deficient mice.
PubMed: Effect of bleeding on hemoglobin contents and lipid oxidation in the skipjack muscle.
PubMed: Expression of oxidative stress-related molecules in circulating leukocytes and urine in patients with chronic viral hepatitis.
PubMed: Protein modifications by 4-hydroxynonenal and 4-hydroxyhexenal in light-exposed rat retina.
PubMed: Estimation of daily exposure to 4-hydroxy-2-alkenals in Korean foods containing n-3 and n-6 polyunsaturated fatty acids.
PubMed: Telmisartan inhibits both oxidative stress and renal fibrosis after unilateral ureteral obstruction in acatalasemic mice.
PubMed: In situ detection of oxidized n-3 polyunsaturated fatty acids in chronic hepatitis C: correlation with hepatic steatosis.
PubMed: Degradation of glyceraldehyde-3-phosphate dehydrogenase triggered by 4-hydroxy-2-nonenal and 4-hydroxy-2-hexenal.
PubMed: Toxicity and detoxification of lipid-derived aldehydes in cultured retinal pigmented epithelial cells.
PubMed: Reduced effect on apoptosis of 4-hydroxyhexenal and oxidized LDL enriched with n-3 fatty acids from postmenopausal women.
PubMed: Comparison between exhaled and sputum oxidative stress biomarkers in chronic airway inflammation.
PubMed: Accumulation of protein-bound 4-hydroxy-2-hexenal in spinal cords from patients with sporadic amyotrophic lateral sclerosis.
PubMed: Induction of endothelial iNOS by 4-hydroxyhexenal through NF-kappaB activation.
PubMed: NF-kappaB activation mechanism of 4-hydroxyhexenal via NIK/IKK and p38 MAPK pathway.
PubMed: Radical scavenger edaravone developed for clinical use ameliorates ischemia/reperfusion injury in rat kidney.
PubMed: Induction of endothelial apoptosis by 4-hydroxyhexenal.
PubMed: Specific markers of lipid peroxidation issued from n-3 and n-6 fatty acids.
PubMed: Protein-bound 4-hydroxy-2-hexenal as a marker of oxidized n-3 polyunsaturated fatty acids.
PubMed: Acatalasemia sensitizes renal tubular epithelial cells to apoptosis and exacerbates renal fibrosis after unilateral ureteral obstruction.
PubMed: Oxidation of 4-hydroxy-2-nonenal by succinic semialdehyde dehydrogenase (ALDH5A).
PubMed: Determination of patterns of biologically relevant aldehydes in exhaled breath condensate of healthy subjects by liquid chromatography/atmospheric chemical ionization tandem mass spectrometry.
PubMed: Covalent binding of hydroxy-alkenals 4-HDDE, 4-HHE, and 4-HNE to ethanolamine phospholipid subclasses.
PubMed: The NADPH:quinone oxidoreductase P1-zeta-crystallin in Arabidopsis catalyzes the alpha,beta-hydrogenation of 2-alkenals: detoxication of the lipid peroxide-derived reactive aldehydes.
PubMed: Cellular lipid peroxidation end-products induce apoptosis in human lens epithelial cells.
PubMed: N-acetylserotonin suppresses hepatic microsomal membrane rigidity associated with lipid peroxidation.
PubMed: Enrichment of eggs with n-3 polyunsaturated fatty acids: effects of vitamin E supplementation.
PubMed: Involvement of lipid peroxidation in spontaneous pancreatitis in WBN/Kob rats.
PubMed: Involvement of caspases in 4-hydroxy-alkenal-induced apoptosis in human leukemic cells.
PubMed: Formation of 4-hydroxy-2-alkenals in barley leaves.
PubMed: Lipid peroxidation and the oxidative burst associated with infection of capsicum annuum by botrytis cinerea
PubMed: Tandem mass spectrometry of model peptides modified with trans-2-hexenal, a product of lipid peroxidation.
PubMed: Formation of lipoxygenase-pathway-derived aldehydes in barley leaves upon methyl jasmonate treatment.
PubMed: Reduction of 4-hydroxynonenal and 4-hydroxyhexenal by retinal aldose reductase.
PubMed: Facile and general method for preparation of (E)-4-hydroxy-2-alkenals.
PubMed: Cellular response to the redox active lipid peroxidation products: induction of glutathione S-transferase P by 4-hydroxy-2-nonenal.
PubMed: Oxygenation of (3Z)-alkenal to (2E)-4-hydroxy-2-alkenal in soybean seed (Glycine max L.).
PubMed: Monoclonal antibodies for detection of 4-hydroxynonenal modified proteins.
PubMed: Cytotoxic and chemotactic potencies of several aldehydic components of oxidised low density lipoprotein for human monocyte-macrophages.
PubMed: 4-Hydroxyhexenal is a potent inducer of the mitochondrial permeability transition.
PubMed: Hydroxyalkenal formation induced by advanced glycosylation of low density lipoprotein.
PubMed: Inhibition of adenine nucleotide translocator by lipid peroxidation products.
PubMed: Generation, characterization, and histochemical application of monoclonal antibodies selectively recognizing oxidatively modified apoB-containing serum lipoproteins.
PubMed: The monoclonal antibody specific for the 4-hydroxy-2-nonenal histidine adduct.
PubMed: Quantitative measurement of 4-hydroxyalkenals in oxidized low-density lipoprotein by gas chromatography-mass spectrometry.
PubMed: Genotoxic properties of 4-hydroxyalkenals and analogous aldehydes.
PubMed: 4-Hydroxynonenal, a metabolite of lipid peroxidation, activates phospholipase D in vascular endothelial cells.
PubMed: Oxygenation of (3Z)-nonenal to (2E)-4-hydroxy-2-nonenal in the broad bean (Vicia faba L.).
PubMed: Analysis of mercapturic acid conjugates of xenobiotic compounds using negative ionization and tandem mass spectrometry.
PubMed: Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes.
PubMed: Effect of 4-hydroxylalkenals on hepatic phosphatidylinositol-4,5-bisphosphate-phospholipase C.
PubMed: 4-Hydroxyhexenal: a lipid peroxidation product derived from oxidized docosahexaenoic acid.
PubMed: Detection of new epitopes formed upon oxidation of low-density lipoprotein, lipoprotein (a) and very-low-density lipoprotein. Use of an antiserum against 4-hydroxynonenal-modified low-density lipoprotein.
PubMed: Effects of the pyrrolizidine alkaloid senecionine and the alkenals trans-4-OH-hexenal and trans-2-hexenal on intracellular calcium compartmentation in isolated hepatocytes.
PubMed: Lipid peroxidation and cellular damage caused by the pyrrolizidine alkaloid senecionine, the alkenal trans-4-hydroxy-2-hexenal, and related alkenals.
PubMed: Distribution of trans-4-hydroxy-2-hexenal and tandem mass spectrometric detection of its urinary mercapturic acid in the rat.
PubMed: Autoxidation of human low density lipoprotein: loss of polyunsaturated fatty acids and vitamin E and generation of aldehydes.
PubMed: In vitro effects of trans-4-hydroxy-2-alkenals on mouse liver cytochrome P-450.
PubMed: Role of cellular calcium homeostasis in toxic liver injury induced by the pyrrolizidine alkaloid senecionine and the alkenal trans-4-OH-2-hexenal.
PubMed: 2,3,7,8-Tetrachlorodibenzo-p-dioxin causes elevation of the levels of the protein tyrosine kinase pp60c-src.
PubMed: Formation of cyclic adducts of deoxyguanosine with the aldehydes trans-4-hydroxy-2-hexenal and trans-4-hydroxy-2-nonenal in vitro.
PubMed: Cytotoxicity, DNA fragmentation and sister-chromatid exchange in Chinese hamster ovary cells exposed to the lipid peroxidation product 4-hydroxynonenal and homologous aldehydes.
PubMed: Metabolism of the pyrrolizidine alkaloid metabolite trans-4-hydroxy-2-hexenal by mouse liver aldehyde dehydrogenases.
PubMed: In vivo covalent binding of trans-4-hydroxy-2-hexenal to rat liver macromolecules.
PubMed: trans-4-Hydroxy-2-hexenal: a reactive metabolite from the macrocyclic pyrrolizidine alkaloid senecionine.
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