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Extra info for Review of Organic Functional Groups: Introduction to Medicinal Organic Chemistry
The metabolism of phenols is much like that of alcohols. The phenol may be oxidized, or, using the terminology previously used for aromatic oxidation, the phenol may be hydroxylated, to give a diphenolic compound (Fig. 7-5) (phase 1 reaction). In most cases, the new OH group will be either ortho or para to the original hydroxyl group. Hydroxylation reactions are commonly catalyzed by members of the cytochrome P450 family of enzymes. The most common form of metabolism of phenols is conjugation with glucuronic acid to form the glucuronide or sulfonation to give the sulfate conjugate (phase 2 reaction).
A thiol functional group is readily oxidized by molecular oxygen to a disulfide dimer. An example of such an instability is seen with the (continued) 10166_ch08 28/06/10 12:20 PM Page 40 40 REVIEW OF ORGANIC FUNCTIONAL GROUPS Thiol Oxidation (continued) drug captopril which is oxidized in solution to its dimer. The thiol–disulfide interconversion plays a significant role in the three-dimensional structure of proteins. 1 Opioid analgesics are potent pain relievers that work in the brain and spinal cord (CNS).
Another significant property of phenols is their chemical reactivity. An important reaction is shown in Figure 7-3. Because phenol is a weak acid, it will not react with sodium bicarbonate, a weak base, but will react with strong bases such as sodium hydroxide or potassium hydroxide to give the respective phenolate salts. FIGURE 7-3. Acid-base reaction between phenol and a strong base. Salt formation is an important reaction since the phenolates formed are ions and will dissolve in water through the much stronger ion-dipole bonding.