Disease relevance of hexanal

• Analysis of headspace volatiles by gas chromatography-mass spectrometry, after addition of the substrate to E. coli extracts expressing the protein, confirmed enzyme-activity data, since cis-3-hexenal was produced by the enzymatic activity of the encoded protein, whereas hexanal production was limited [1].
• To assess the physiological role of TomloxC in the generation of volatile C6 aldehyde and alcohol flavor compounds, we produced transgenic tomato plants with greatly reduced TomloxC using sense and antisense constructs under control of the cauliflower mosaic virus 35S promoter [2].
• OBJECTIVE: To investigate whether inhaled nitric oxide (NO) enhances pulmonary lipid peroxidation as indicated by arterial blood levels of malondialdehyde, hexanal, and pentanal in patients with acute respiratory distress syndrome (ARDS) [3].
• In this work, we developed a new approach to the analysis of the lung cancer biomarkers, hexanal and heptanal in human blood that was based on headspace single-drop microextraction (HS-SDME) with droplet derivatization, followed by gas chromatography-mass spectrometry (GC-MS) [4].
• Pentanal and n-hexanal were metabolized by Bifidobacterium breve MB233 [5].

Psychiatry related information on hexanal

• Our previous study revealed that the odor of hexanal, which is derived from the wood chips used as bedding, influenced mouse maternal behavior and induced the neonatal death of Fyn-deficient (fyn(-/-)) pups born of fyn(-/-) parents [6].
• Hexanal is a key organoleptic element of green-note that is found in both fragrances and flavors [7].

High impact information on hexanal

• Although these transgenic plants have highly reduced levels of both hexanal and 3-hexenal, they show no phenotypic differences compared with wild-type ones, particularly in regard to the expression of wound-induced genes [8].
• To test the hypothesis that GST-catalyzed GSH conjugation can effectively prevent inhibition of t-RA synthesis by aldehydic products of lipid peroxidation, triethyltin bromide (TEB, a potent inhibitor of GST, 20 microM) was added to ARHC-catalyzed reactions when hexanal or tNE were present in the incubations [9].
• Mutants act1 and fad5, which are deficient in C16 unsaturated fatty acids, had wild-type levels of C6-aldehyde production [10].
• The differences in C6-aldehyde formation among the fatty acid mutants of Arabidopsis appeared not to result from alteration of lipoxygenase/hydroperoxide lyase pathway enzymes [10].
• The short- and longer-chain saturated aldehydes acetaldehyde and hexanal and the dialdehyde MDA were considerably less effective at inhibiting LCAT than were acrolein and HNE [11].

Chemical compound and disease context of hexanal

• The HPOL activity obtained by expressing the cDNA in Escherichia coli formed n-hexanal from linoleic acid 13-hydroperoxide, whereas linoleic acid 9-hydroperoxide was not a substrate for the enzyme [12].
• The percentage of hepatic fibrosis, plasma malondialdehyde concentration and alanine aminotransferase activity were measured as well as the following aldehydes: hexanal, octanal, decanal, 2-hexenal, 2-octenal, 2-nonenal, 2,4-heptadienal and 2,4-decadienal [13].
• Exposure to hexanal odor influences maternal behavior and induces neonatal death in Fyn tyrosine kinase-deficient mice [14].

Biological context of hexanal

• Kinetics of formation of fluorescent products from hexanal and L-lysine in a two-phase system [15].
• The biomimetic polymers consist of a poly(vinyl amine) (PVAm) backbone with hexanal branches and varying ratios of cell binding peptide (RGD) to carbohydrate (maltose) [16].
• It was concluded that hydrocarbon gases are better indices of lipid peroxidation than hexanal, which is enzymatically metabolized, and acetone, the production of which is dominated by factors such as altered carbohydrate metabolism [17].
• Literature studies were included to describe the formation of hexanal and carbon monoxide and the toxicology of hexanal [18].
• Hexanal also is produced in the ozone-initiated autoxidation of any n-6 polyunsaturated fatty acid, and thus is a measure of generalized oxidative stress [19].

Anatomical context of hexanal

• In fyn(-/-) females, hexanal also induced the activation of the medial preoptic area and the basolateral and posteriomedial cortical amygdala, which are known to be involved in the control of maternal and emotional behavior [6].
• We previously described a rapid headspace gas chromatographic method for the determination of hexanal, an important decomposition product of n-6 polyunsaturated fatty acid (PUFA) peroxidation in rat liver samples and human red blood cell membranes [20].
• Increases in 4-hydroxynonenal and hexanal in bone marrow of rats subjected to total body X-ray irradiation: association with antioxidant vitamins [21].
• ALDH activity toward acetaldehyde in liver mitochondria from subjects with a mutant allele was less than 10% of that with two alleles of wild-type, and the activities toward formaldehyde, propionaldehyde, n-butyraldehyde, capronaldehyde, and heptaldehyde were also significantly lower in the ALDH2*1/*2 rather than ALDH2*1/*1 group [22].
• At an a(w) of 0.30, 34.7 and 39.7 microg of hexanal/g of myofibril were detected by GC/MS-SPME and CI-ELISA, respectively, after 4 days of storage [23].

Associations of hexanal with other chemical compounds

• CPD patients exhibited high plasma MDA concentrations [371 (287 to 468) nM], whereas hexanal was in the low normal range [56 (51 to 81) nM] [24].
• Microgram per m(3) (sub-ppb) levels of the aliphatic aldehydes, propanal, 1-butanal, 1-heptanal, and 1-hexanal, in ambient air were successfully determined by HPLC separation with fluorometric detection [25].
• Study of peptides containing modified lysine residues by tandem mass spectrometry: precursor ion scanning of hexanal-modified peptides [26].
• The in vitro antioxidant activity of L. alba essential oil, obtained by hydrodistillation was evaluated by determination of hexanal, the main carbonyl compound released by linoleic acid subjected to peroxidation (1 mm Fe2+, 37 degrees C, 12 h), and by quantification of this acid as its methyl ester [27].
• The steady-state fluorescence in the octanol phase was attributed to two components with fluorescence lifetimes at 25 degrees C of 0.7 +/- 0.05 ns and 5.1 +/- 0.2 ns, assigned to hexanal and the condensation product, respectively [15].

Gene context of hexanal

• In addition, Fyn-deficient females exhibited defects in the maternal behavior of nest building and pup retrieval, regardless of exposure to hexanal [14].
• Exposure of HVSMC to hexanal for 2 h led to TF protein levels up to seven times higher than untreated cells whereas 2,4-DDE for 30 min led to them being up to 2.2 times higher [28].
• Cyclic voltammetry of ferredoxin and WOR5 on an activated glassy carbon electrode shows a catalytic wave upon addition of hexanal, suggesting that ferredoxin can be a physiological redox partner [29].
• Very high concentrations of hexanal (200 microM) were needed to inhibit TNF-alpha expression (23%, P<0.001) [30].
• Hexanal induced Fos immunoreactivity in the primary olfactory cortex and in the medial and central amygdala of both fyn(+/-) and fyn(-/-) mice [6].

Analytical, diagnostic and therapeutic context of hexanal

• Then, a reversed-phase high-performance liquid chromatographic technique (HPLC) was employed to quantify hexanal in the form of 2,4-dinitrophenylhydrazone derivative [31].
• Rapid headspace gas chromatography of hexanal as a measure of lipid peroxidation in biological samples [32].
• Reverse phase high performance liquid chromatography confirmed that the primary alkanal component was hexanal, while the primary hydroxyalkenal was 4-hydroxynoneal [33].
• We report a novel process for the production of hexanal using immobilized enzyme templates extracted from different plant sources in combination with hollow-fiber ultrafiltration for in situ separation [7].
• To clarify what regions of the brain are involved in this effect, we examined which brain regions of fyn(-/-) and Fyn-heterozygous (fyn(+/-)) females were activated by hexanal odor using Fos immunohistochemistry [6].

References