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Chemical compound From Wikipedia, the free encyclopedia
2-Hydroxyisobutyric acid is the organic compound with the formula (CH3)2C(OH)CO2H. A white solid, it is classified as an hydroxycarboxylic acid. It has been considered as a naturally occurring precursor to polyesters.[3] It is closely related to lactic acid (CH3CH(OH)CO2H).[4]
Names | |
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Other names
α-Hydroxyisobutyric acid 2-Hydroxyisobutanoic acid α-Hydroxyisobutanoic acid 2-Hydroxy-2-methyl propanoic acid 2-Hydroxy-2-methyl propionic acid 2-Methyllactic acid 2-Methylglycolic acid Acetonic acid Hydroxydimethylacetic acid | |
Identifiers | |
3D model (JSmol) |
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1744739 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.008.955 |
EC Number |
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PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C4H8O3 | |
Molar mass | 104.105 g·mol−1 |
Appearance | white solid |
Density | 1.23 g/cm3[1] |
Melting point | 82.5 °C (180.5 °F; 355.6 K) |
Boiling point | 212 °C (414 °F; 485 K) |
Hazards | |
GHS labelling:[2] | |
Danger | |
H302, H315, H318, H335 | |
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The enzyme 2-hydroxyisobutyryl coenzyme A (CoA) mutase isomerizes 3-hydroxybutyryl coenzyme A into 2-hydroxyisobutyryl coenzyme A. Hydrolysis of the latter gives 2-hydroxyisobutyric acid.[5]
The amides formed from this carboxylic acid and the ε-amino group of lysine residues are a kind of post translational modification.[6][7]
Ethyl methacrylate (an industrially important monomer and ester of methacrylic acid) was first obtained by treating the ethyl ester of 2-hydroxyisobutyric acid with phosphorus pentachloride in an apparent dehydration reaction.[8]
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