Record Information
Version1.0
Creation date2011-09-21 00:04:23 UTC
Update date2020-09-17 15:40:45 UTC
Primary IDFDB021877
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-3-Hydroxyisobutyric acid
Description(S)-3-Hydroxyisobutyric acid, also known as (S)-3-hydroxy-2-methylpropanoate or 3-hydroxy-isobutyrate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom (S)-3-Hydroxyisobutyric acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (S)-3-Hydroxyisobutyric acid exists in all living species, ranging from bacteria to humans. The severity of this disease varies from case to case (S)-3-hydroxyisobutyric acid can be converted into (S)-methylmalonic acid semialdehyde through its interaction with the enzymes 3-hydroxyisobutyrate dehydrogenase, mitochondrial and enoyl-CoA hydratase, mitochondrial. In humans, (S)-3-hydroxyisobutyric acid is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway (S)-3-Hydroxyisobutyric acid is an intermediate in the metabolic pathways of L-valine and L-thymine amino acids. The deficient enzyme in 3HiB-uria remains unclear (S)-3-Hydroxyisobutyric acid is a potentially toxic compound (S)-3-Hydroxyisobutyric acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, colorectal cancer, and diabetes mellitus type 2; (S)-3-hydroxyisobutyric acid has also been linked to the inborn metabolic disorder 3-hydroxyisobutyric aciduria.
CAS Number2068-83-9
Structure
Thumb
Synonyms
SynonymSource
(S)-3-Hydroxy-2-methylpropanoic acidChEBI
(S)-3-Hydroxy-2-methylpropionic acidChEBI
(S)-3-Hydroxy-2-methylpropanoateGenerator
(S)-3-Hydroxy-2-methylpropionateGenerator
(S)-3-HydroxyisobutyrateGenerator
2-Methyl-L-(+)-hydracrylateHMDB
2-Methyl-L-(+)-hydracrylic acidHMDB
3-Hydroxy(iso)butyric acidHMDB
3-Hydroxy-2-methyl-(S)-propanoateHMDB
3-Hydroxy-2-methyl-(S)-propanoic acidHMDB
3-Hydroxy-2-methylpropanoateHMDB
3-Hydroxy-2-methylpropanoic acidHMDB
3-Hydroxy-isobutyrateHMDB
3-HydroxyisobutyrateHMDB
3-Hydroxyisobutyric acidHMDB
(2S)-3-Hydroxy-2-methylpropanoic acidHMDB
(2S)-3-Hydroxy-2-methylpropionic acidHMDB
(S)-beta-Hydroxyisobutyric acidHMDB
(S)-Β-hydroxyisobutyric acidHMDB
(±)-3-hydroxy-2-methylpropanoic acidHMDB
(±)-3-hydroxy-2-methylpropionic acidHMDB
2-(Hydroxymethyl)propanoic acidHMDB
2-(Hydroxymethyl)propionic acidHMDB
2-Methyl-3-hydroxypropanoic acidHMDB
2-Methyl-3-hydroxypropionic acidHMDB
3-HIBAHMDB
3-Hydroxy-2-methylpropionic acidHMDB
DL-3-Hydroxyisobutyric acidHMDB
L-(+)-beta-Hydroxyisobutyric acidHMDB
L-(+)-Β-hydroxyisobutyric acidHMDB
beta-Hydroxyisobutyric acidHMDB
Β-hydroxyisobutyric acidHMDB
3-Hydroxy-2-isobutyrateHMDB
3-Hydroxy-2-isobutyric acidHMDB
(S)-3-Hydroxyisobutyric acidHMDB
2-methyl-L-(+)-Hydracrylatehmdb
2-methyl-L-(+)-Hydracrylic acidhmdb
3-hydroxy-2-methyl-(S)-Propanoatehmdb
3-hydroxy-2-methyl-(S)-Propanoic acidhmdb
3-hydroxy-isobutyratehmdb
Predicted PropertiesNot Available
Chemical FormulaC4H8O3
IUPAC name
InChI IdentifierInChI=1S/C4H8O3/c1-3(2-5)4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
InChI KeyDBXBTMSZEOQQDU-VKHMYHEASA-N
Isomeric SMILESC[C@@H](CO)C(O)=O
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
Classification
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID389707
ChEMBL IDNot Available
KEGG Compound IDC06001
Pubchem Compound ID440873
Pubchem Substance IDNot Available
ChEBI ID18064
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00023
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID37034
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxyisobutyryl-CoA hydrolase, mitochondrialHIBCHQ6NVY1
Pathways
NameSMPDB LinkKEGG Link
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference