Amadori rearrangement

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The Amadori rearrangement or Amadori reaction describes a reaction from organic chemistry . It describes the 2nd step of the Maillard reaction , a non-enzymatic browning. During migration arising from unstable Aldosylaminen stable 1-amino-1-desoxyketosen. The reaction bears the name of its discoverer, the Italian pharmaceutical chemist Mario Amadori (1886–1941).

The corresponding reaction starting from a ketosis to an amino al can is called the Heyns rearrangement .

The reaction leads to flavorings such as those found in coffee, bread, roasts and caramel.

mechanism

This chemical reaction initially leads to the formation of an enol (4), which is stabilized by shifting a hydrogen atom from the OH group to the C-1 position.

Amadori rearrangement

Individual evidence

  1. Bernd Schäfer: Natural substances in the chemical industry , Spectrum Akademischer Verlag, 2007, pp. 168–173, ISBN 978-3-8274-1614-8 .

literature

Web links

Commons : Amadori rearrangement  - collection of images, videos and audio files