2-Hydroxyisobutyric acid

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]

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
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).
Infobox references

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 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]

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. Bhatia, Shashi Kant; Bhatia, Ravi Kant; Yang, Yung-Hun (2016). "Biosynthesis of Polyesters and Polyamide Building Blocks Using Microbial Fermentation and Biotransformation". Reviews in Environmental Science and Bio/Technology. 15 (4): 639–663. doi:10.1007/s11157-016-9415-9. S2CID 88561532.
  4. Miltenberger, Karlheinz (2000). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507.
  5. Rohde, Maria-Teresa; Tischer, Sylvi; Harms, Hauke; Rohwerder, Thore (2017). "Production of 2-Hydroxyisobutyric Acid from Methanol by Methylobacterium extorquens AM1 Expressing ( R )-3-Hydroxybutyryl Coenzyme A-Isomerizing Enzymes". Applied and Environmental Microbiology. 83 (3). Bibcode:2017ApEnM..83E2622R. doi:10.1128/AEM.02622-16. PMC 5244315. PMID 27836853.
  6. Dai, Lunzhi; Peng, Chao; Montellier, Emilie; Lu, Zhike; Chen, Yue; Ishii, Haruhiko; Debernardi, Alexandra; Buchou, Thierry; Rousseaux, Sophie; Jin, Fulai; Sabari, Benjamin R.; Deng, Zhiyou; Allis, C David; Ren, Bing; Khochbin, Saadi; Zhao, Yingming (2014). "Lysine 2-Hydroxyisobutyrylation is a Widely Distributed Active Histone Mark". Nature Chemical Biology. 10 (5): 365–370. doi:10.1038/nchembio.1497. PMID 24681537.
  7. Carrola, Joana; Rocha, CláUdia M.; Barros, António S.; Gil, Ana M.; Goodfellow, Brian J.; Carreira, Isabel M.; Bernardo, João; Gomes, Ana; Sousa, Vitor; Carvalho, Lina; Duarte, Iola F. (2011). "Metabolic Signatures of Lung Cancer in Biofluids: NMR-Based Metabonomics of Urine". Journal of Proteome Research. 10 (1): 221–230. doi:10.1021/pr100899x. PMID 21058631.
  8. E. Frankland, B. F. Duppa (1865). "Untersuchungen über Säuren aus der Acrylsäure-Reihe; 1) Umwandlung der Säuren aus der Milchsäure-Reihe in die der Acrylsäure-Reihe". Justus Liebigs Annalen der Chemie. 136: 12. doi:10.1002/jlac.18651360102.


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