3-Hydroxyisobutyric acid

3-Hydroxyisobutyric acid
Names

Preferred IUPAC name 3-Hydroxy-2-methylpropanoic acid
Other names 3-Hydroxyisobutyric acid
Identifiers
CAS Number	2068-83-9^Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	1745484
ChEBI	CHEBI:18064^Y
ChemSpider	85^Y
ECHA InfoCard	100.254.271
EC Number	819-819-7
KEGG	C01188^Y
PubChem CID	87
UNII	K75C8JDF5W^Y
InChI InChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)^Y Key: DBXBTMSZEOQQDU-UHFFFAOYSA-N^Y InChI=1/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7) Key: DBXBTMSZEOQQDU-UHFFFAOYAC
SMILES OC(C(C)CO)=O O=C(O)C(C)CO
Properties
Chemical formula	C₄H₈O₃
Molar mass	104.10 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

3-Hydroxyisobutyric acid (or 3-hydroxy-2-methylpropanoic acid)^[1] is an intermediate in the metabolism of valine.^[2] It is a chiral compound having two enantiomers, D-3-hydroxyisobutyric acid and L-3-hydroxyisobutyric acid.

References

^ PubChem. "3-Hydroxyisobutyric acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-24.
^ "Human Metabolome Database: Showing metabocard for (S)-3-Hydroxyisobutyric acid (HMDB0000023)". hmdb.ca. Retrieved 2022-11-24.

Amino acid metabolism metabolic intermediates

K→acetyl-CoA

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→	N′-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→
citrate

glycine→ serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid
isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA
methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA