Glycolic acid
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| Glycolic acid | |
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| IUPAC name | 2-Hydroxyethanoic acid |
| Other names | glycolic acid, hydroxyacetic acid |
| Identifiers | |
| CAS number | |
| RTECS number | MC5250000 |
| SMILES | O=C(O)CO |
| Properties | |
| Molecular formula | C2H4O3 |
| Molar mass | 76.05 g/mol |
| Appearance | colorless solid |
| Density | 1.27 g/cm3 |
| Melting point |
75 °C |
| Boiling point |
decomposes |
| Solubility in water | 0.1 g/mL |
| Solubility in other solvents | alcohols, acetone, acetic acid and ethyl acetate[1] |
| Acidity (pKa) | 3.83 |
| Hazards | |
| Main hazards | Corrosive (C) |
| NFPA 704 |
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| R-phrases | R22-R34 |
| S-phrases | S26-S36/37/39-S45 |
| Flash point | 129 °C[1] |
| Related Compounds | |
| Related α-hydroxy acids | lactic acid |
| Related compounds | acetic acid, glycerol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references | |
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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.[1]
References
External links
Acne-treating agents (D10) | |
|---|---|
| Topical agents | Azelaic acid • Benzoyl peroxide • Glycolic acid • Light therapy • Salicylic acid • Tea tree oil |
| Antibiotics | Clindamycin • Erythromycin • Sulfacetamide • Tetracyclines • Trimethoprim |
| Hormonal | Antiandrogens • Contraceptives |
| Retinoids | Adapalene • Isotretinoin • Tazarotene • Tretinoin |
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Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
