Alpha hydroxy acid
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α-Hydroxy acids, or alpha hydroxy acids (AHAs), are a class of chemical compounds that consist of a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. They may be either naturally occurring or synthetic. AHAs are well known for their use in the cosmetics industry. They are often found in products that aid in the reduction of wrinkles as well as to soften strong, defining lines and improve the overall look and feel of the skin. They are also used as chemical peels available in a dermatologist's office, beauty and health spas and home kits, which usually contain a lower concentration of around 4%. Effective results through continuous treatment have resulted in AHAs being a successful & developmental method of curbing harsh ageing effects in the skin & cosmeceutical industry.
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 to be effective, including AHA, it must penetrate into the skin where it can act on living cells. Bioavailability (influenced primarily by small molecular size) is an important factor in a 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.
AHAs 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.
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.
α-Hydroxy acids are useful building blocks in organic synthesis. For example, α-hydroxy acids are generally useful as precursors in the preparation aldehydes via oxidative cleavage. Compounds of this class are used on the industrial-scale and include glycolic acid, lactic acid, citric acid, and mandelic acid.
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. 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. 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.[unreliable source?]
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 stronger glycolic acid concentrations (50 - 70%) as well as prime the skin for deeper chemical peels such as TCA peel (trichloroacetic acid).
At highest 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.[unreliable source?] 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").
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.
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.
- Kempers, S; Katz, HI; Wildnauer, R; Green, B (June 1998). "An evaluation of the effect of an alpha hydroxy acid-blend skin cream in the cosmetic improvement of symptoms of moderate to severe xerosis, epidermolytic hyperkeratosis, and ichthyosis.". Cutis. 61 (6): 347–350. PMID 9640557.
- "Alpha Hydroxy Acids for Skin Care". Cosmetic Dermatology, Supplement: 1–6. October 1994.
- Ditre CM, Griffin TD, Murphy GF, Vasn Scott EJ: Improvement of photodamaged skin with alpha-hydroxy acid (AHA): A clinical, histological, and ultra-structural study. Dermatology 2000 Congress. Vienna, Austria. May 18–21, 1993:175.
- Ôeda, Haruomi (1934). "Oxidation of some α-hydroxy-acids with lead tetraacetate". Bulletin of the Chemical Society of Japan. 9 (1): 8–14. doi:10.1246/bcsj.9.8.
- Nwaukwa, Stephen; Keehn, Philip (1982). "Oxidative cleavage of α-diols, α-diones, α-hydroxy-ketones and α-hydroxy- and α-keto acids with calcium hypochlorite [Ca(OCl)2]". Tetrahedron Letters. 23 (31): 3135–3138. doi:10.1016/S0040-4039(00)88578-0.
- Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_507.
- Ritzer, Edwin; Sundermann, Rudolf (2000). "Hydroxycarboxylic Acids, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_519.
- Kalla, G; Garg, A; Kachhawa, D (2001). "Chemical peeling - Glycolic acid versus trichloroacetic acid in melasma". Indian Journal of Dermatology, Venereology and Leprology. 67 (2): 82–4. PMID 17664715.
- Atzori, L.; Brundu, M.A.; Orru, A.; Biggio, P. (1999). "Glycolic acid peeling in the treatment of acne". European Academy of Dermatology and Venereology. 12 (2): 119–122. doi:10.1111/j.1468-3083.1999.tb01000.x.
- Ronald L. Moy; Debra Luftman; Lenore S. Kakita (2002). Glycolic Acid Peels. CRC Press. ISBN 9780824744595.
- Peter Pacik. "What Is Glycolic Acid?".
- Dawson, R. M. C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- Handbook of Chemistry and Physics, CRC Press, 58th edition, page D147 (1977)
- Kurtzweil, Paula (March–April 1998). "Alpha Hydroxy Acids for Skin Care". FDA Consumer. Archived from the original on February 7, 2006.
- PERRICONE, NICHOLAS V.; DiNARDO, JOSEPH C. (May 1996). "Photoprotective and Antiinflammatory Effects of Topical Glycolic Acid". Dermatologic Surgery. 22 (5): 435–437. PMID 8634805. doi:10.1111/j.1524-4725.1996.tb00343.x.