2-Hydroxyisobutyric acid

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2-Hydroxyisobutyric acid
Names
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
)
1744739
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.008.955 Edit this at Wikidata
EC Number
  • 209-848-8
UNII
  • InChI=1S/C4H8O3/c1-4(2,7)3(5)6/h7H,1-2H3,(H,5,6)
    Key: BWLBGMIXKSTLSX-UHFFFAOYSA-N
  • CC(C)(C(=O)O)O
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]
GHS02: FlammableGHS07: Exclamation mark
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).

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]

Occurrences

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

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]

See also

References

  1. ^ W.P.J.Gaykema; J.A.Kanters; G.Roelofsen (1978), Cryst. Struct. Commun., 47: 463
  2. ^ "2-Hydroxyisobutyric acid". pubchem.ncbi.nlm.nih.gov.
  3. S2CID 88561532
    .
  4. ISBN 978-3527306732
    .
  5. PMID 27836853
    .
  6. PMID 24681537
    .
  7. PMID 21058631
    .
  8. doi:10.1002/jlac.18651360102
    .
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