Hydroxylation
chemical reaction
In chemistry, hydroxylation refers to the installation of a hydroxyl group (−OH) into an organic compound. Hydroxylations generate alcohols and phenols, which are very common functional groups. Hydroxylation confers some degree of water-solubility. Hydroxylation of a hydrocarbon is an oxidation, thus a step in degradation.
Atmospheric hydroxylation
Hydroxylation via reaction with tropospheric hydroxyl radicals and oxygen is one possible pathway for the degradation of aromatic compounds:
ArH + •OH ⇌ [Ar(OH)H]•
[Ar(OH)H]• + O2 → ArOH + HO2•
Biological hydroxylation
In biochemistry, hydroxylation reactions are often facilitated by enzymes called hydroxylases. These enzymes insert an O atom into a C−H bond. Typical stoichiometries for the hydroxylation of a generic hydrocarbon are these:
2R3C−H + O2 → 2 R3C−OH
R3C−H + O2 + 2e− + 2H+ → R3C−OH + H2O
Since O2 itself is a slow and unselective hydroxylating agent, catalysts are required to accelerate the pace of the process and to introduce selectivity.
Hydroxylation is important in detoxification since it converts lipophilic compounds into water-soluble (hydrophilic) products that are more readily removed by the kidneys or liver and excreted. Some drugs (for example, steroids) are activated or deactivated by hydroxylation.
The principal hydroxylation catalyst in nature is cytochrome P-450, hundreds of variations of which are known.
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