17046-01-4Relevant articles and documents
Synthesis and properties of natural occurring α-hydroxyaldehydes
Kern, Werner,Spiteller, Gerhard
, p. 4347 - 4362 (1996)
A synthesis for aliphatic α-acetoxyaldehydes 18 is presented. These were converted to free aldehydes 9 by action of hog liver esterase. Aliphatic α-hydroxyaldehydes, recently recognized to be produced in the course of lipid-peroxidation of linoleic and other unsaturated fatty acids, are only stable for short time in solution. They react with amines to give Schiff bases. These are instable, but can be trapped after reduction with NaBH4 to the corresponding amines. Since α-hydroxyaldehydes are produced in the case of lipid peroxidation and were found to stimulate oxidative stress, Schiff base formation might be a physiological important process. α-Hydroxyaldehydes form under physiological conditions mercaptals by reaction with thiols.
Photo-irradiation of α-halo carbonyl compounds: A novel synthesis of α-hydroxy- and α,α′-dihydroxyketones
Chai, Wen,Takeda, Akihiro,Hara, Makoto,Ji, Shun-Jun,Horiuchi, C. Akira
, p. 2453 - 2463 (2007/10/03)
The reaction of α-halo ketones (α-iodocycloalkanones, α-bromocycloalkanones, α-iodo-β-alkoxy esters, and α-iodoacyclicketones) with irradiation under a high-pressure mercury lamp gave the corresponding α-hydroxyketones in good yields. For α-bromoketones, it was found that α-hydroxylation does not occur. However, α-bromoketones were converted into α-hydroxyketones in the presence of KI. In the case of α,α′-diiodo ketones, α,α′-dihydroxyketones, which up to now have scarcely been reported, were obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxy- and α,α′- dihydroxyketones.
