Glycolic acid
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| Names | |||
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IUPAC name
2-Hydroxyethanoic acid
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| Other names
dicarbonous acid
glycolic acid hydroxyacetic acid hydroacetic acid |
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| Identifiers | |||
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3D model (Jmol)
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| ChEBI | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.001.073 | ||
| KEGG | |||
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PubChem CID
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| RTECS number | MC5250000 | ||
| UNII | |||
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| Properties | |||
| C2H4O3 | |||
| Molar mass | 76.05 g/mol | ||
| Appearance | white, powdery solid | ||
| Density | 1.49 g/cm3 | ||
| Melting point | 75 °C (167 °F; 348 K) | ||
| Boiling point | decomposes | ||
| 70% solution | |||
| Solubility in other solvents |
alcohols, acetone, acetic acid and ethyl acetate |
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| Acidity (pKa) | 3.83 | ||
| Hazards | |||
| Main hazards | Corrosive (C) | ||
| R-phrases | R22-R34 | ||
| S-phrases | S26-S36/37/39-S45 | ||
| NFPA 704 | |||
| Flash point | 129 °C (264 °F; 402 K) | ||
| Related compounds | |||
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Related α-hydroxy acids
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Lactic acid | ||
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Related compounds
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Glycolaldehyde Acetic acid Glycerol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Glycolic acid (hydroacetic acid or hydroxyacetic acid); chemical formula C2H4O3 (also written as HOCH2CO2H), is the smallest α-hydroxy acid (AHA). This colorless, odorless, and hygroscopic crystalline solid is highly soluble in water. It is used in various skin-care products. Glycolic acid is found in some sugar-crops. A glycolate or glycollate is a salt or ester of glycolic acid.
The name "glycolic acid" was coined in 1848 by French chemist Auguste Laurent (1807–1853). He proposed that the amino acid glycine — which was then called glycocolle — might be the amine of a hypothetical acid, which he called "glycolic acid" (acide glycolique).
Glycolic acid was first prepared in 1851 by German chemist Adolph Strecker (1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877). They produced it by a treating hippuric acid with nitric acid and nitrogen dioxide to form an ester of benzoic acid and glycolic acid (C6H5C(=O)OCH2COOH), which they called "benzoglycolic acid" (Benzoglykolsäure), (also benzoyl glycolic acid). They boiled the ester for days with dilute sulfuric acid, thereby obtaining benzoic acid and glycolic acid (Glykolsäure).
Glycolic acid can be synthesized in various ways. The predominant approaches uses a catalyzed reaction of formaldehyde with synthesis gas (carbonylation of formaldehyde), for its low cost.
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