Glycolic acid

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Template:Chembox E numberTemplate:Chembox SolubilityInWater
Glycolic acid
IUPAC name 2-Hydroxyethanoic acid
Other names glycolic acid,
hydroxyacetic acid
Identifiers
3D model (JSmol)
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RTECS number MC5250000
Properties
C2H4O3
Molar mass 76.05 g/mol
Appearance colorless solid
Density 1.27 g/cm3
Melting point
Boiling point
Solubility in other solvents alcohols, acetone,
acetic acid and
ethyl acetate[1]
Acidity (pKa) 3.83
Hazards
Main hazards Corrosive (C)
R-phrases R22-R34
S-phrases S26-S36/37/39-S45
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

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Overview

Glycolic acid (or hydroxyacetic acid) is the smallest α-hydroxy acid (AHA). It appears in the form of a colorless, odorless and hydroscopic crystalline solid that is highly soluble in water and related solvents. Glycolic acid is associated with sugar-crops and is isolated from sugarcane, sugar beets, pineapple, canteloupe, and unripe grapes.

Uses

Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel performed by a dermatologist in concentrations of 20%-80% or at-home kits in lower concentrations of 10%. It is used to improve the skin's appearance and texture. It may reduce wrinkles, acne scarring, hyperpigmentation and improve many other skin conditions. Once applied, glycolic acid reacts with the upper layer of the epidermis, weakening the binding properties of the lipids that hold the dead skin cells together. This allows the outer skin to "dissolve" revealing the underlying skin.

Glycolic acid is also a useful intermediate for organic synthesis, in a range of reactions including: oxidation-reduction, esterification and long chain polymerization. It is used as a monomer in the preparation of polyglycolic acid and other biocompatible copolymers (e.g. PLGA). Among other uses this compound finds employment in the textile industry as a dyeing and tanning agent, in food processing as a flavoring agent and as a preservative. Glycolic acid is often included into emulsion polymers, solvents and additives for ink and paint in order to improve flow properties and impart gloss.

Preparation

Glycolic acid is isolated from natural sources and is inexpensively available. It can be prepared by the reaction of chloroacetic acid with sodium hydroxide followed by re-acidification.

Safety

Glycolic acid is a mild irritant.[3]


References

  1. "DuPont Glycolic Acid Technical Information". Retrieved 2006-07-06.
  2. "Glycolic Acid MSDS". University of Akron. Retrieved 2006-09-18.
  3. "Glycolic Acid MSDS". ICSC:NENG1537 International Chemical Safety Cards (WHO/IPCS/ILO). Retrieved 2006-06-08. Text " CDC/NIOSH " ignored (help)

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