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Glycolic acid

Glycolic acid
Chemical structure of glycolic acid
Ball-and-stick model of glycolic acid
Names
IUPAC name
2-Hydroxyethanoic acid
Other names
dicarbonous acid
glycolic acid
hydroxyacetic acid
hydroacetic acid
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.001.073
KEGG
PubChem CID
RTECS number MC5250000
UNII
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
Acidity (pKa) 3.83
Hazards
Main hazards Corrosive (C)
R-phrases R22-R34
S-phrases S26-S36/37/39-S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity (yellow): no hazard code Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 129 °C (264 °F; 402 K)
Related compounds
Lactic acid
Related compounds
Glycolaldehyde
Acetic acid
Glycerol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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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