Cosmetic applications
Understanding skin structure and cutaneous aging is helpful to a discussion of the topical action of AHAs. Human skin has two principal components, the avascular epidermis and the underlying vascular dermis. Cutaneous aging, while having epidermal concomitants, seems to involve primarily the dermis and is caused by intrinsic and extrinsic aging factors.
AHAs are a group of organic carboxylic compounds. AHAs most commonly used in cosmetic applications are typically derived from food products including glycolic acid (from sugar cane), lactic acid (from sour milk), malic acid (from apples), citric acid (from citrus fruits) and tartaric acid (from grape wine). For any topical compound, including AHA, it must penetrate into the skin where it can act on living cells. Bioavailability (influenced primarily by small molecular size) is one characteristic that is important in determining compound’s ability to penetrate the top layer of the skin. Glycolic acid having the smallest molecular size is the AHA with greatest bioavailability and penetrates the skin most easily; this largely accounts for the popularity of this product in cosmetic applications.
[edit] Epidermal effectAHAs have a profound effect on keratinization; which is clinically detectable by the formation of a new stratum corneum. It appears that AHAs modulate this formation through diminished cellular cohesion between corneocytes at the lowest levels of the stratum corneum. [edit] Dermal effects
AHAs with greater bioavailability appear to have deeper dermal effects. Glycolic acid, lactic acid and citric acid, on topical application to photodamaged skin, have been shown to produce increased amounts of mucopolysaccharides and collagen and increased skin thickness without detectable inflammation, as monitored by skin biopsies[4] [edit] Alpha hydroxy acids at different concentrations
In low concentrations, 5 – 10%, as is found in many over-the-counter products, glycolic acid reduces cell adhesion in the top layer of the skin. This action promotes exfoliation of the outermost layer of the skin accounting for smoother texture following regular use of topical glycolic acid (GA). This relatively low concentration of GA lends itself to daily use as a monotherapy or a part of a broader skin care management for such conditions as acne, photo-damage, wrinkling as well as melasma.[5][6] Care needs to be taken to avoid irritation as this may result in worsening of melasma or other pigmentary problems. Newer formulations combine glycolic acid with an amino acid such as arginine and form a time-release system that reduces the risk of irritation without affecting glycolic acid efficacy[7]. The use of an anti-irritant like allantoin is also helpful. Because of its safety, glycolic acid at the concentrations below 10% can be used daily by most people except those with very sensitive skin[8].
In higher concentrations, between 10 and 50%, its benefits are more pronounced but are limited to temporary skin smoothing without much long lasting results. This is still a useful concentration to use as it can prepare the skin for more efficacious glycolic acid concentrations (50 – 70%) as well as prime the skin for deeper chemical peels such as TCA peel (trichloroacetic acid).
At higher concentrations, 50-70% applied for 3 to 8 minutes under the supervision of a physician, glycolic acid promotes slitting between the cells and can be used to treat acne or photo-damage (such as mottled dyspigmentation, melasma or fine wrinkles). The benefits from such short contact application (chemical peels) depend on the pH of the solution (the more acidic the product, or the lower the pH, the more pronounced the results), the concentration of GA (higher concentrations produce more vigorous response), the length of application and prior skin conditioning such as prior use of topical vitamin A products. Although single application of 50 – 70% GA will produce beneficial results, multiple treatments every 2 to 4 weeks are required for optimal results[9]. It is important to understand that glycolic acid peels are chemical peels with similar risks and side effects as other peels. Some of the side effects of AHAs chemical peeling can include hyper-pigmentation, persistent redness, scarring, as well as flare up of facial herpes infections (“cold sores”).
[edit] 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[10] versus 4.87[11])
