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4-Hydroxymandelic acid

4-Hydroxymandelic acid is a chemical compound used to synthesize atenolol. The compound typically occurs as a monohydrate.

Synthesis and occurrence

It is produced from 4-hydroxypyruvic acid by the action of the enzyme (S)-p-hydroxymandelate synthase:

HOC<sub>6</sub>H<sub>4</sub>CH<sub>2</sub>C(O)CO<sub>2</sub>H + O<sub>2</sub> → HOC<sub>6</sub>H<sub>4</sub>CH(OH)CO<sub>2</sub>H + CO2

4-Hydroxymandelic acid can be synthesized by the condensation reaction of phenol and glyoxylic acid:

HOC<sub>6</sub>H<sub>5</sub> + CHOCO<sub>2</sub>H → HOC<sub>6</sub>H<sub>4</sub>CH(OH)CO<sub>2</sub>H

See also

References