4-hydroxynonenal

Structural formula
	Structural formula of the ( E ) -form with incomplete stereochemistry
General
Surname	4-hydroxynonenal
other names	4-HNE; HNE; trans -4-hydroxy-2-nonenal; ( E ) -4-hydroxy-2-nonenal; ( S ) - ( E ) -4-hydroxy-2-nonenal; ( RS ) - ( E ) -4-hydroxy-2-nonenal;
Molecular formula	C 9 H 16 O 2
External identifiers / databases
PubChem	5283344
Wikidata	Q229982
properties
Molar mass	156.22 g mol −1
Physical state	liquid
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

4-hydroxynonenal is a reactive α, β-unsaturated aldehyde selected from the lipid peroxidation multiple unsaturated fatty acids (engl. Polyunsaturated fatty acids - PUFAs ) produced. During this process, proteins are in turn modified under conditions of oxidative stress , i. H. damaged.

history

4-HNE was characterized by Hermann Esterbauer and since then a large number of publications on this substance have appeared.

Biological importance

4-HNE has been linked to various diseases, especially Alzheimer's , cancer and arteriosclerosis .

Isomerism

4-Hydroxynonenal contains an asymmetrically substituted carbon-carbon double bond and an additional stereogenic center. Hence there are four isomeric compounds:

( E , R ) -4-hydroxynonenal,
( E , S ) -4-hydroxynonenal,
( Z , R ) -4-hydroxynonenal and
( Z , S ) -4-hydroxynonenal.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Mikel R. Roe, Hongwei Xie, Sricharan Bandhakavi and Timothy J. Griffin: Using complementary hydrazide chemistry based methods with precursor-ion scanning to characterize potential in vivo sites of HNE modification , ASMS 2006, engl.
↑ Esterbauer, H., Schaur, RJ, Zollner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Rad Biol Med. 1991; 11: 8-1128.

Web links

HNE club - an interest group for HNE research

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[2] Mikel R. Roe, Hongwei Xie, Sricharan Bandhakavi and Timothy J. Griffin: Using complementary hydrazide chemistry based methods with precursor-ion scanning to characterize potential in vivo sites of HNE modification , ASMS 2006, engl.

[3] Esterbauer, H., Schaur, RJ, Zollner, H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Rad Biol Med. 1991; 11: 8-1128.