Chemical acidity
Although these compounds are related to the ordinary carboxylic acids, and therefore are weak acids, their chemical structure allows for the formation of an internal hydrogen bond between the hydrogen at the hydroxyl group and one of the oxygen atoms of the carboxylic group. Two effects emerge from this situation:
• Due to the "occupation" of electrons of the carboxylic oxygens in the hydrogen bonding, the acidic proton is held less strongly, as the same electrons are used in bonding that hydrogen too. So the pKa of 2-hydroxypropanoic acid (lactic acid) is a full unit lower compared to that of propionic acid itself (3.86 versus 4.87)
• The internal bridging hydrogen is locked in its place on the NMR timescale: in mandelic acid (2-hydroxy-2-phenylacetic acid) this proton couples to the one on carbon in the same way and magnitude as hydrogens on geminal carbon atoms.
Safety
AHAs are generally safe when used on the skin as a cosmetic agent using the recommended dosage. The most common side-effects are mild skin irritations, redness and flaking. The severity usually depends on the pH and the concentration of the acid used. Chemical peels tend to have more severe side-effects including blistering, burning and skin discoloration, although they are usually mild and go away a day or two after treatment.
The FDA has also warned consumers that care should be taken when using AHAs after an industry-sponsored study found that they can increase photosensitivity to the sun. Other sources suggest that Glycolic acid, in particular, may confer a photoprotective effect.
Chemical acidityAlthough these compounds are related to the ordinary carboxylic acids, and therefore are weak acids, their chemical structure allows for the formation of an internal hydrogen bond between the hydrogen at the hydroxyl group and one of the oxygen atoms of the carboxylic group. Two effects emerge from this situation:• Due to the "occupation" of electrons of the carboxylic oxygens in the hydrogen bonding, the acidic proton is held less strongly, as the same electrons are used in bonding that hydrogen too. So the pKa of 2-hydroxypropanoic acid (lactic acid) is a full unit lower compared to that of propionic acid itself (3.86 versus 4.87)• The internal bridging hydrogen is locked in its place on the NMR timescale: in mandelic acid (2-hydroxy-2-phenylacetic acid) this proton couples to the one on carbon in the same way and magnitude as hydrogens on geminal carbon atoms.SafetyAHAs are generally safe when used on the skin as a cosmetic agent using the recommended dosage. The most common side-effects are mild skin irritations, redness and flaking. The severity usually depends on the pH and the concentration of the acid used. Chemical peels tend to have more severe side-effects including blistering, burning and skin discoloration, although they are usually mild and go away a day or two after treatment.The FDA has also warned consumers that care should be taken when using AHAs after an industry-sponsored study found that they can increase photosensitivity to the sun. Other sources suggest that Glycolic acid, in particular, may confer a photoprotective effect.
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