2-Hydroxyisobutyric acid

Last updated
2-Hydroxyisobutyric acid
2-HydroxyisobutyricAcid.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-848-8
PubChem CID
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
Appearancewhite 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]
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
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]

Contents

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

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketene</span> Organic compound of the form >C=C=O

In organic chemistry, a ketene is an organic compound of the form RR'C=C=O, where R and R' are two arbitrary monovalent chemical groups. The name may also refer to the specific compound ethenone H2C=C=O, the simplest ketene.

Transesterification is the process of exchanging the organic functional group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction can also be accomplished with the help of other enzymes, particularly lipases.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.

<span class="mw-page-title-main">Transamination</span> Chemical reaction that transfers an amino group to a ketoacid

Transamination is a chemical reaction that transfers an amino group to a ketoacid to form new amino acids. This pathway is responsible for the deamination of most amino acids. This is one of the major degradation pathways which convert essential amino acids to non-essential amino acids.

<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

<span class="mw-page-title-main">Carbamate</span> Chemical group (>N–C(=O)–O–)

In organic chemistry, a carbamate is a category of organic compounds with the general formula R2NC(O)OR and structure >N−C(=O)−O−, which are formally derived from carbamic acid. The term includes organic compounds, formally obtained by replacing one or more of the hydrogen atoms by other organic functional groups; as well as salts with the carbamate anion H2NCOO.

<span class="mw-page-title-main">Isobutyric acid</span> Carboxylic acid with chemical formula (CH3)2CHCO2H

Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of n-butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.

<span class="mw-page-title-main">Cinnamic acid</span> Chemical compound

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

<span class="mw-page-title-main">Formate</span> Salt or ester of formic acid

Formate is the conjugate base of formic acid. Formate is an anion or its derivatives such as ester of formic acid. The salts and esters are generally colorless.

<span class="mw-page-title-main">Polyester</span> Category of polymers, in which the monomers are joined together by ester links

Polyester is a category of polymers that contain the ester functional group in every repeat unit of their main chain. As a specific material, it most commonly refers to a type called polyethylene terephthalate (PET). Polyesters include naturally occurring chemicals, such as in plants and insects, as well as synthetics such as polybutyrate. Natural polyesters and a few synthetic ones are biodegradable, but most synthetic polyesters are not. Synthetic polyesters are used extensively in clothing.

The Gabriel–Colman rearrangement is the chemical reaction of a saccharin or phthalimido ester with a strong base, such as an alkoxide, to form substituted isoquinolines. First described in 1900 by chemists Siegmund Gabriel and James Colman, this rearrangement, a ring expansion, is seen to be general if there is an enolizable hydrogen on the group attached to the nitrogen, since it is necessary for the nitrogen to abstract a hydrogen to form the carbanion that will close the ring. As shown in the case of the general example below, X is either CO or SO2.

<i>beta</i>-Hydroxybutyric acid Chemical compound

β-Hydroxybutyric acid, also known as 3-hydroxybutyric acid or BHB, is an organic compound and a beta hydroxy acid with the chemical formula CH3CH(OH)CH2CO2H; its conjugate base is β-hydroxybutyrate, also known as 3-hydroxybutyrate. β-Hydroxybutyric acid is a chiral compound with two enantiomers: D-β-hydroxybutyric acid and L-β-hydroxybutyric acid. Its oxidized and polymeric derivatives occur widely in nature. In humans, D-β-hydroxybutyric acid is one of two primary endogenous agonists of hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor (GPCR).

Acetyl-CoA synthetase (ACS) or Acetate—CoA ligase is an enzyme involved in metabolism of acetate. It is in the ligase class of enzymes, meaning that it catalyzes the formation of a new chemical bond between two large molecules.

<i>beta</i>-Hydroxybutyryl-CoA Chemical compound

β-Hydroxybutyryl-CoA is an intermediate in the fermentation of butyric acid, and in the metabolism of lysine and tryptophan. The L-3-hydroxybutyl-CoA enantiomer is also the second to last intermediate in beta oxidation of even-numbered, straight chain, and saturated fatty acids.

<span class="mw-page-title-main">3-hydroxyacyl-CoA dehydrogenase</span> Enzyme

In enzymology, a 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">3-Hydroxybutyryl-CoA dehydrogenase</span>

In enzymology, a 3-hydroxybutyryl-CoA dehydrogenase (EC 1.1.1.157) is an enzyme that catalyzes the chemical reaction

Hydroxycarboxylic acids are carboxylic acids containing one or more hydroxy (alcohol) functional groups. They are of particular interest because several are bioactive and some are useful precursors to polyesters. The inventory is large.

<span class="mw-page-title-main">Ethyl methacrylate</span> Organic compound

Ethyl methacrylate is the organic compound with the formula C2H5O2CC(CH3)=CH2. A colorless liquid, it is a common monomer for the preparation of acrylate polymers. It is typically polymerized under free-radical conditions.

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.