Thioglycolic acid
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| Names | |
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Preferred IUPAC name
Sulfanylacetic acid
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| Other names
2-Sulfanylacetic acid
2-Mercaptoacetic acid Acetyl mercaptan Mercaptoacetate Mercaptoacetic acid Thioglycolic acid Thiovanic acid |
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| Identifiers | |
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3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.000.616 |
| KEGG | |
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PubChem CID
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| Properties | |
| C2H4O2S | |
| Molar mass | 92.11 g·mol−1 |
| Appearance | colorless, clear liquid |
| Odor | strong, disagreeable |
| Density | 1.32 g/cm3 |
| Melting point | −16 °C (3 °F; 257 K) |
| Boiling point | 96 °C (205 °F; 369 K) at 5 mmHg |
| miscible | |
| Vapor pressure | 10 mmHg (17.8°C) |
| -50.0·10−6 cm3/mol | |
| Hazards | |
| Flash point | > 110 °C; 230 °F; 383 K |
| Explosive limits | 5.9%-? |
| US health exposure limits (NIOSH): | |
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PEL (Permissible)
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none |
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REL (Recommended)
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TWA 1 ppm (4 mg/m3) [skin] |
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IDLH (Immediate danger)
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N.D. |
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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 | |
Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. TGA is miscible with polar organic solvents.
TGA is used as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to ammonium thioglycolate that is used for permanents. TGA and its derivatives break the disulfide bonds in the cortex of hair. One reforms these broken bonds in giving hair a "perm." Alternatively and more commonly, the process leads to depilation as is done commonly in leather processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media. In fact thioglycolysis reactions used on condensed tannins to study their structure.
Organotin derivatives of thioglycolic acid isooctyl esters are widely used as stabilzers for PVC. These species have the formula R2Sn(SCH2CO2C8H17)2.
Applying TGA can soften nails and then fix pincer nails in the correct position.
Sodium thioglycolate is a component of a special bacterial growth media : thioglycolate broth. It is also used in so-called "fallout remover" or "wheel cleaner" to remove iron oxide residue from rims.Ferrous ion combines with thioglycolate to form red-violet ferric thioglycolate.
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Wikipedia