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Chemical Compound Review

CHEMBL450072     (E)-non-2-enal

Synonyms: CCRIS 3326, CCRIS 9203, Non-2-enal, CHEBI:61726, LS-2988, ...
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Disease relevance of beta-Hexylacrolein

  • Although tolrestat treatment increased immunoreactivity of the lesion with antibodies raised against protein adducts of the lipid peroxidation product 4-hydroxy trans-2-nonenal, no compensatory increase in lesion fibrosis was observed [1].
  • The ESI-MS spectrum of the soluble fraction used in the toxicity tests, demonstrated that conjugation of T2N with Mb yielded Mb adducts with one residue of trans-2-nonenal per myoglobin molecule as the major fraction and adducts with different numbers of T2N molecules as minor fractions [2].

High impact information on beta-Hexylacrolein

  • Oxidative conversion of all-trans-retinal (t-RAL, 18 microM) to t-RA catalyzed by rat conceptal cytosol (RCC) was sensitive to inhibition by trans-2-nonenal (tNE), nonyl aldehyde (NA), 4-hydroxy-2-nonenal (4HNE), and hexanal [3].
  • Identification of biochemical pathways for the metabolism of oxidized low-density lipoprotein derived aldehyde-4-hydroxy trans-2-nonenal in vascular smooth muscle cells [4].
  • Modification of the reconstituted membranes with malondialdehyde, trans-2-nonenal, or n-heptaldehyde did not affect the ALP activity, suggesting that the secondary degraded products of lipid hydroperoxides had no influence on the enzyme activity [5].
  • Our objective was to characterize protein, lipid, and lipoxygenase activities and fatty acid compositions in food soybeans and to determine how chemical composition and enzyme activities related to the generation of beany odor components, including hexanal, hexanol, trans-2-nonenal, 1-octen-3-ol, and trans-2,trans-4-decadienal in soymilk [6].
  • From our aroma extract dilu-tion analyses (AEDA) applied to naturally aged lager beers emerged an old-beer-like odorant at RICP-SIL 5 CB = 1532 and RIFFAP = 2809, with a FD value close to that of trans-2-nonenal (the well-known cardboard off-flavor found in aged beers) [7].

Biological context of beta-Hexylacrolein


Anatomical context of beta-Hexylacrolein

  • This study investigates the toxic effect of E(2)nonenal (trans-2-nonenal, T2N) and its conjugate with horse muscle myoglobin (Mb) tested on murine cell line L929 and human cell line A549, as well as the genotoxic effect of these compounds assayed by measuring of micronuclei in human cells K562 [2].

Associations of beta-Hexylacrolein with other chemical compounds


Gene context of beta-Hexylacrolein

  • In contrast, ALDH1A1 expression provided only moderate protection against trans-2-nonenal (t2NE), and none against the other six-nine carbon aldehydes [9].
  • PTP was effectively inhibited by physiological amounts of trans-2-nonenal (1-10 microM) [11].


  1. Contribution of aldose reductase to diabetic hyperproliferation of vascular smooth muscle cells. Srivastava, S., Ramana, K.V., Tammali, R., Srivastava, S.K., Bhatnagar, A. Diabetes (2006) [Pubmed]
  2. The cytotoxic and genotoxic effects of conjugated trans-2-nonenal (T2N), an off-flavor compound in beer and heat processed food arising from lipid oxidation. Dey, E.S., Staniszewska, M., Paściak, M., Konopacka, M., Rogoliński, J., Gamian, A., Danielsson, B. Pol. J. Microbiol. (2005) [Pubmed]
  3. 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]
  4. Identification of biochemical pathways for the metabolism of oxidized low-density lipoprotein derived aldehyde-4-hydroxy trans-2-nonenal in vascular smooth muscle cells. Srivastava, S., Conklin, D.J., Liu, S.Q., Prakash, N., Boor, P.J., Srivastava, S.K., Bhatnagar, A. Atherosclerosis (2001) [Pubmed]
  5. Oxygen radical-induced inhibition of alkaline phosphatase activity in reconstituted membranes. Ohyashiki, T., Kumada, Y., Hatanaka, N., Matsui, K. Arch. Biochem. Biophys. (1994) [Pubmed]
  6. Selected odor compounds in soymilk as affected by chemical composition and lipoxygenases in five soybean materials. Yuan, S., Chang, S.K. J. Agric. Food Chem. (2007) [Pubmed]
  7. Identification of a stale-beer-like odorant in extracts of naturally aged beer. Callemien, D., Dasnoy, S., Collin, S. J. Agric. Food Chem. (2006) [Pubmed]
  8. Enzymatic hydrogenation of trans-2-nonenal in barley. Hambraeus, G., Nyberg, N. J. Agric. Food Chem. (2005) [Pubmed]
  9. Selective protection by stably transfected human ALDH3A1 (but not human ALDH1A1) against toxicity of aliphatic aldehydes in V79 cells. Townsend, A.J., Leone-Kabler, S., Haynes, R.L., Wu, Y., Szweda, L., Bunting, K.D. Chem. Biol. Interact. (2001) [Pubmed]
  10. Hydroperoxy-arachidonic acid mediated n-hexanal and (Z)-3- and (E)-2-nonenal formation in Laminaria angustata. Boonprab, K., Matsui, K., Akakabe, Y., Yotsukura, N., Kajiwara, T. Phytochemistry (2003) [Pubmed]
  11. Structural characteristics of a lipid peroxidation product, trans-2-nonenal, that favour inhibition of membrane-associated phosphotyrosine phosphatase activity. Hernández-Hernández, A., Garabatos, M.N., Rodríguez, M.C., Vidal, M.L., López-Revuelta, A., Sánchez-Gallego, J.I., Llanillo, M., Sánchez-Yagüe, J. Biochim. Biophys. Acta (2005) [Pubmed]
  12. The formation of cis-3-nonenal, trans-2-nonenal and hexanal from linoleic acid hydroperoxide isomers by a hydroperoxide cleavage enzyme system in cucumber (Cucumis sativus) fruits. Galliard, T., Phillips, D.R., Reynolds, J. Biochim. Biophys. Acta (1976) [Pubmed]
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