Alpha Hydroxy Acid

Alpha hydroxy acids are a group of natural acids found in foods. Alpha hydroxy acids include citric acid (found
in citrus fruits), glycolic acid (found in sugar cane), lactic acid (found in sour milk), malic acid (found in
apples), tartaric acid (found in grapes), and others.
Some people take malic acid by mouth with magnesium for treating pain and tenderness associated with
fibromyalgia.
Various alpha hydroxy acids are applied to the skin (used topically) for moisturizing and removing dead skin
cells, for treating acne and improving the appearance of acne scars, for improving the appearance of photo-aged
skin, and firming and smoothing skin.
Alpha hydroxy acids are also used topically to treat extremely dry skin (xerosis), an inherited disease marked by
dry, scaly skin (ichthyosis), and a condition that causes darkening of the skin (melasma). When this condition
develops in pregnant women, it is sometimes called the mask of pregnancy.
Not all cosmetics that contain alpha hydroxy acid have the concentration information on the label. For safetys
sake, its best to use products that identify the concentration of active ingredients.
-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 claiming to reduce wrinkles or the signs of aging, 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%. Although there is some evidence for their
effectiveness,[1][non-primary source needed] cosmetic producers have made exaggerated claims of
performance.[2] Many well-known -hydroxy acids are useful building blocks in organic synthesis: the most
common and simple are glycolic acid, lactic acid, citric acid, mandelic acid
How does it work?
Alpha hydroxy acids seem to work by removing the top layers of dead skin cells. They can also increase the
thickness of deeper layers of skin, promoting firmness.
Likely Effective for :
Treating sun damage when applied to the skin in a cream or lotion, but alpha hydroxy skin peels do not
seem to work for this use.
Treating dry skin when applied to the skin in a cream or lotion.
Possibly Effective for :
Acne when applied to the skin in a cream or lotion.
Acne scars when applied to the skin in a facial peel or lotion. Applying glycolic acid, an alpha hydroxy
acid, as a facial peel or lotion seems to improve the appearance of acne scars. Applying 70% glycolic
acid in a series of peels seems to work better than using 15% glycolic acid lotion daily. However, 15%
glycolic acid lotion seems to be moderately effective in people who cannot tolerate facial peels.
Reducing pain and tenderness caused by fibromyalgia when a specific alpha hydroxy acid, called malic
acid, is used in combination with magnesium.
Reducing the pigmentation associated with a skin disorder called melasma. Applying 10% glycolic acid
as a lotion for 2 weeks followed by a facial peeling program using 50% glycolic acid every month for 3
consecutive months seems to reduce unwanted skin coloration in people with two of the three types of
melasma, epidermal-type and mixed-type melasma. However, glycolic acid facial peels dont seem to
work for the third type of melasma, dermal-type melasma.
Insufficient Evidence for:
Treating an inherited skin disorder that causes dry, scaly skin (ichthyosis).

Other conditions.

Side Effect and Safety

Alpha hydroxy acids at a concentration of 10% or less as a lotion or cream are LIKELY SAFE for most people
when applied to the skin appropriately and as directed. In some people, alpha hydroxy acids can make the skin
extra sensitive to sunlight. Be sure to use a sunscreen while using alpha hydroxy acid products.
Alpha hydroxy acids can also cause mild skin irritation, redness, swelling, itching, and skin discoloration.
Facial peels, lotions, and creams with a concentration greater than 10% should only be used under the
supervision of a dermatologist. Facial peels can cause moderate to severe skin irritation, redness, and burning.
Facial peels left on the skin for periods longer than recommended can cause severe burns to the skin.
When taken by mouth, the alpha hydroxy acid called malic acid is POSSIBLY SAFE when used short-term.
Some people can have side effects including diarrhea, nausea, and general stomach discomfort.
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.[10] Other sources suggest that Glycolic acid, in
particular, may confer a photoprotective effect
Special Precautions & Warnings:
Pregnancy and breast-feeding: Alpha hydroxy creams at a concentration of 10% or less are LIKELY SAFE
when applied to the skin during pregnancy and breast-feeding. But dont take malic acid (the form of alpha
hydroxy acids that is generally taken by mouth). Not enough is known about the safety of malic acid during
pregnancy and breast-feeding.
Sensitive skin: Alpha hydroxy acids can worsen skin conditions by causing skin irritation and removal of the
top layer of skin cells.
Dosing
APPLIED TO THE SKIN:
For treating skin wrinkled and aged by sunlight: Alpha hydroxy acid products containing lactic acid,
tartaric acid, gluconolactone, or glycolic acid (GA) in 8% concentration are used. The alpha hydroxy
acid gluconolactone has also been used in a 14% solution. These products are usually applied to the skin
twice daily.
For improving the appearance of acne scars: glycolic acid (GA) facial peels are used. Peels of increasing
strength of 20%, 35%, 50%, and 70% are applied every two weeks. Peels are applied first for 2 minutes
and then for a longer time (up to 4-5 minutes) before applying the next stronger solution. Completing the
series at least 6 times is usually needed before skin looks better. People who do not like facial peels
often use 15% GA lotion daily long-term instead.
For lightening brown patches due to a condition called melasma: a 10% lotion of the glycolic acid (GA)
is applied with a sunscreen to facial skin nightly for 2 weeks. Then a peeling program is done monthly
for 3 months in a row. The peeling program features a 50% GA peel applied three times to the face and
left on for a period of 2-5 minutes each time (first peel 2 minutes, second peel 4 minutes, and third peel
5 minutes).

Cosmetic Application
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.
Epidermal Effect
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.
Dermal Effect
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
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.[4][5] 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.[6] 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.[7][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.[7][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").
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 2hydroxypropanoic acid (lactic acid) is a full unit lower compared to that of propionic acid itself (3.86[8] versus
4.87[9])
The internal bridging hydrogen is locked in its place on the NMR timescale: in mandelic acid (2-hydroxy-2phenylacetic acid) this proton couples to the one on carbon in the same way and magnitude as hydrogens on
geminal carbon atoms.