An expeditious synthesis of 4-hydroxy-2E-nonenal (4-HNE), its dimethyl acetal and of related compounds.
The facile one step synthesis of 4-hydroxy-2E-nonenal and its dimethyl acetal via a cross-metathesis reaction between commercially available octen-3-ol and acrolein or its dimethyl acetal is reported. The method was extended to the synthesis of C6 and C12 4-hydroxy-2E-enals, their dimethyl acetal and of the 4-hydroxy-2E-nonenoic acid (4-HNA).
Soulère
Laurent
L
ICBMS, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, université de Lyon, université Lyon 1, CNRS, UMR 5246, Lyon F-69622, France. laurent.soulere@insa-lyon.fr
Queneau
Yves
Y
Doutheau
Alain
A
D000080:Acetals / Q000138:chemical synthesis* / Q000737:chemistry; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001671:Biochemistry / Q000379:methods*; D002384:Catalysis; D015853:Cysteine Proteinase Inhibitors / Q000494:pharmacology*; D017665:Hydroxyl Radical; D015227:Lipid Peroxidation; D008055:Lipids / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D015203:Reproducibility of Results
D000080:Acetals; D000447:Aldehydes; D015853:Cysteine Proteinase Inhibitors; D008055:Lipids; D017665:Hydroxyl Radical; C027576:4-hydroxy-2-nonenal; C059033:1,1-dimethoxyethane