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Chemical Compound Review

HEXANAL     hexanal

Synonyms: Hexaldehyde, Caproaldehyde, Hexanaldehyde, Hexylaldehyde, Kapronaldehyd, ...
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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


Biological context of hexanal


Anatomical context of hexanal


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].


  1. Molecular characterization of an Arabidopsis gene encoding hydroperoxide lyase, a cytochrome P-450 that is wound inducible. Bate, N.J., Sivasankar, S., Moxon, C., Riley, J.M., Thompson, J.E., Rothstein, S.J. Plant Physiol. (1998) [Pubmed]
  2. Identification of a specific isoform of tomato lipoxygenase (TomloxC) involved in the generation of fatty acid-derived flavor compounds. Chen, G., Hackett, R., Walker, D., Taylor, A., Lin, Z., Grierson, D. Plant Physiol. (2004) [Pubmed]
  3. Inhaled nitric oxide does not enhance lipid peroxidation in patients with acute respiratory distress syndrome. Weigand, M.A., Snyder-Ramos, S.A., Möllers, A.G., Bauer, J., Hansen, D., Kochen, W., Martin, E., Motsch, J. Crit. Care Med. (2000) [Pubmed]
  4. Gas chromatography-mass spectrometric analysis of hexanal and heptanal in human blood by headspace single-drop microextraction with droplet derivatization. Li, N., Deng, C., Yin, X., Yao, N., Shen, X., Zhang, X. Anal. Biochem. (2005) [Pubmed]
  5. Characterization of Bifidobacterium strains for use in soymilk fermentation. Scalabrini, P., Rossi, M., Spettoli, P., Matteuzzi, D. Int. J. Food Microbiol. (1998) [Pubmed]
  6. Exposure to hexanal odor induces extraordinary Fos expression in the medial preoptic area and amygdala of Fyn tyrosine kinase-deficient mice. Hamaguchi-Hamada, K., Hamada, S., Yagi, T. Brain Res. Mol. Brain Res. (2004) [Pubmed]
  7. Use of a plant-derived enzyme template for the production of the green-note volatile hexanal. Schade, F., Thompson, J.E., Legge, R.L. Biotechnol. Bioeng. (2003) [Pubmed]
  8. Hydroperoxide lyase depletion in transgenic potato plants leads to an increase in aphid performance. Vancanneyt, G., Sanz, C., Farmaki, T., Paneque, M., Ortego, F., Castañera, P., Sánchez-Serrano, J.J. Proc. Natl. Acad. Sci. U.S.A. (2001) [Pubmed]
  9. Inhibition of embryonic retinoic acid synthesis by aldehydes of lipid peroxidation and prevention of inhibition by reduced glutathione and glutathione S-transferases. Chen, H., Juchau, M.R. Free Radic. Biol. Med. (1998) [Pubmed]
  10. The impact of alteration of polyunsaturated fatty acid levels on C6-aldehyde formation of Arabidopsis thaliana leaves. Zhuang, H., Hamilton-Kemp, T.R., Andersen, R.A., Hildebrand, D.F. Plant Physiol. (1996) [Pubmed]
  11. Inhibition of lecithin-cholesterol acyltransferase and modification of HDL apolipoproteins by aldehydes. McCall, M.R., Tang, J.Y., Bielicki, J.K., Forte, T.M. Arterioscler. Thromb. Vasc. Biol. (1995) [Pubmed]
  12. Molecular cloning and expression of Arabidopsis fatty acid hydroperoxide lyase. Matsui, K., Wilkinson, J., Hiatt, B., Knauf, V., Kajiwara, T. Plant Cell Physiol. (1999) [Pubmed]
  13. Hepatic production of apolar aldehydes in rats with carbon tetrachloride-induced cirrhosis. Ferré, N., Girona, J., Cabré, M., Joven, J., LaVille, A., Masana, L., Paternáin, J.L., Camps, J. Mol. Cell. Biochem. (1999) [Pubmed]
  14. Exposure to hexanal odor influences maternal behavior and induces neonatal death in Fyn tyrosine kinase-deficient mice. Hamaguchi-Hamada, K., Sanbo, C., Hamada, S., Yagi, T. Neurosci. Res. (2004) [Pubmed]
  15. Kinetics of formation of fluorescent products from hexanal and L-lysine in a two-phase system. Stapelfeldt, H., Skibsted, L.H. Lipids (1996) [Pubmed]
  16. Human microvascular endothelial cell growth and migration on biomimetic surfactant polymers. Sagnella, S.M., Kligman, F., Anderson, E.H., King, J.E., Murugesan, G., Marchant, R.E., Kottke-Marchant, K. Biomaterials (2004) [Pubmed]
  17. Volatile hydrocarbon and carbonyl products of lipid peroxidation: a comparison of pentane, ethane, hexanal, and acetone as in vivo indices. Dillard, C.J., Tappel, A.L. Lipids (1979) [Pubmed]
  18. Emission of hexanal and carbon monoxide from storage of wood pellets, a potential occupational and domestic health hazard. Svedberg, U.R., Högberg, H.E., Högberg, J., Galle, B. The Annals of occupational hygiene. (2004) [Pubmed]
  19. Detection of aldehydes in bronchoalveolar lavage of rats exposed to ozone. Pryor, W.A., Bermúdez, E., Cueto, R., Squadrito, G.L. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1996) [Pubmed]
  20. Headspace gas chromatography to determine human low density lipoprotein oxidation. Frankel, E.N., German, J.B., Davis, P.A. Lipids (1992) [Pubmed]
  21. Increases in 4-hydroxynonenal and hexanal in bone marrow of rats subjected to total body X-ray irradiation: association with antioxidant vitamins. Umegaki, K., Sano, M., Suzuki, K., Tomita, I., Esashi, T. Bone Marrow Transplant. (1999) [Pubmed]
  22. Effects of aldehyde dehydrogenase-2 genetic polymorphisms on metabolism of structurally different aldehydes in human liver. Wang, R.S., Nakajima, T., Kawamoto, T., Honma, T. Drug Metab. Dispos. (2002) [Pubmed]
  23. ELISA for monitoring lipid oxidation in chicken myofibrils through quantification of hexanal-protein adducts. Goodridge, C.F., Beaudry, R.M., Pestka, J.J., Smith, D.M. J. Agric. Food Chem. (2003) [Pubmed]
  24. Influence of dialysis on plasma lipid peroxidation products and antioxidant levels. Daschner, M., Lenhartz, H., Bötticher, D., Schaefer, F., Wollschläger, M., Mehls, O., Leichsenring, M. Kidney Int. (1996) [Pubmed]
  25. Polymer-mediated extraction of the fluorescent compounds derived by Hantzsch reaction with dimedone for the sensitive determination of aliphatic aldehydes in air. Saitoh, T., Suzuki, S., Hiraide, M. Journal of chromatography. A (2006) [Pubmed]
  26. Study of peptides containing modified lysine residues by tandem mass spectrometry: precursor ion scanning of hexanal-modified peptides. Fenaille, F., Tabet, J.C., Guy, P.A. Rapid Commun. Mass Spectrom. (2004) [Pubmed]
  27. Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity. Stashenko, E.E., Jaramillo, B.E., Martínez, J.R. Journal of chromatography. A. (2004) [Pubmed]
  28. Aldehydes mediate tissue factor induction: a possible mechanism linking lipid peroxidation to thrombotic events. Cabré, A., Girona, J., Vallvé, J.C., Masana, L. J. Cell. Physiol. (2004) [Pubmed]
  29. WOR5, a novel tungsten-containing aldehyde oxidoreductase from Pyrococcus furiosus with a broad substrate Specificity. Bevers, L.E., Bol, E., Hagedoorn, P.L., Hagen, W.R. J. Bacteriol. (2005) [Pubmed]
  30. 2,4-Decadienal downregulates TNF-alpha gene expression in THP-1 human macrophages. Girona, J., Vallvé, J.C., Ribalta, J., Heras, M., Olivé, S., Masana, L. Atherosclerosis (2001) [Pubmed]
  31. Determination of hexanal as indicator of the lipidic oxidation state in potato crisps using gas chromatography and high-performance liquid chromatography. Sanches-Silva, A., de Quirós, A.R., López-Hernández, J., Paseiro-Losada, P. Journal of chromatography. A. (2004) [Pubmed]
  32. Rapid headspace gas chromatography of hexanal as a measure of lipid peroxidation in biological samples. Frankel, E.N., Hu, M.L., Tappel, A.L. Lipids (1989) [Pubmed]
  33. Analysis of aldehydic lipid peroxidation products by TLC/densitometry. Beckman, J.K., Morley, S.A., Greene, H.L. Lipids (1991) [Pubmed]
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