Frans-2-Nonenal, 538, -2-Nonen

In relation to cancer, there is some evidence that highly oxidized and heated fats may have carcinogenic characteristics. HNE (4-hydroxy-2-frans-nonenal), a secondary lipid peroxidation product derived from linoleic acid oxidation, has assumed particular interest because it has shown cytotoxic and mutagenic properties. Its toxicity, as well other secondary lipid peroxidation products (HHE 4-hydroxy-2-frans-hexenal and HOE 4-h yd roxy-2-trans-oc ten al), is explained through the high reactivity with proteins, nucleic acids, DNA, and RNA. Research links them to different diseases such as atherosclerosis, Alzheimer s, and liver diseases (Seppanen and Csallany, 2006). Research is rapidly progressing, but results are still not conclusive. 

Many materials used for food and beverage packaging have characteristic odors or sensory active compounds (Torri et ah, 2008). The intensity and description of the odor may be affected by the number and type of volatile compounds that are released under environmental conditions at the time of evaluation. Chemical composition of the material and polymer morphology may play a role in the sensory characterization. Sensory descriptors do not define a specific chemical compound but may be related to different compounds, a blend of compounds, and even a limited concentration range of a compound or class of compounds. For example, frans-2-nonenal in water changes in sensory (taste) description from "plastic (0.2 gg/1) to "woody" (0.4-2.0 p.g/1), "fatty" (8-40 pg/1), and "cucumber" (1000 gg/1) (Piringer and Ruter, 2000). Such terms are descriptive of the sensation and perception by human response to the chemical stimuli (Table 2.1). 

Another important example of the Michael addition in biochemistry and molecnlar biology is the reaction of 4-hydroxynon-2-enal with amines and snlfydryl gronps (Winter, C.K., Segall, H.J., and Haddon, W.F., Formation of cyclic addncts of deoxygnanosine with the aldehyde trans-4-hydroxy-2-hexenal and fran.y-4-hydroxy-2-nonenal in vitro. Cancer Res. 46, 5682-5686, 1986 Sayre, L.M., Arora, P.K., Iyer, R.S., and Salomon, R.G., Pyrrole formation from 4-hydroxynonenal and primary amines, Chem. Res. Toxicol. 6, 19-22, 1993 Hartley, D.P, Ruth, J.A., and Petersen,... 

Reaction of the jS-oxidophosphonium ylide (2) with one equivalent of N-chloro-succinimide first at —78° and then at room temperature leads to 2-chloro-cis-2-nonene (7) in about 50% yield. Surprisingly the reaction of (2) with iodobenzene dichloride leads to the isomeric 2-chloro-frans-2-nonene (8). Reactions of (2) with brominating or iodinating reagents failed to give the corresponding halo-... 

The proton that is removed by the base must be anti to bromine. Thus, the alkyl groups must be gauche to one another in the conformation that leads to cti-4-nonene and anti to one another in the one that leads to fran -4-nonene. 

FIGURE 6.4 The structures of 2-aIkenal adducts, (a) The structures of acrolein adducts (1 3). (b) The structures of 2-nonenal adducts (cis- and frans-HHP-lysine) (4 and 5). 

Aldini, G., I. Dalle-Donne, G. Vistoli et al. Covalent modification of actin by 4-hydroxy-frans-2-nonenal (HNE) LC-ESI-MS/MS evidence for Cys374 Michael addnction. Snectrom 40(71. 2005 946-54. 

Calamaras, T. D., C. Lee, F. Lan et al. Post-translational modification of serine/threonine kinase LKBl via adduction of the reactive lipid species 4-hydroxy-fran -2-nonenal (HNE) at lysine residue 97 directly inhibits kinase activity, 287(50), 2012 42400-6. 

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