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3-Hydroxyisovaleric acid (PC000458)

Record Information
Version1.0
Creation date2015-10-09 22:30:48 UTC
Update date2017-01-19 02:36:24 UTC
FoodComEx IDPC000458
FoodDB RecordFDB022225
Chemical Information
Name3-Hydroxyisovaleric acid
Description3-Hydroxyisovaleric acid is a normal human metabolite excreted in the urine. Elevated levels of this compound are found in several inherited disorders such as Dihydrolipoamide dehydrogenase Deficiency, 3-Methylcrotonyl-CoA carboxylase 1 deficiency, 3-Hydroxy-3-methylglutaryl-CoA lyase deficiency (3-hydroxy-3-methylglutaryl -CoA lyase Deficiency, Biotinidase deficiency multiple carboxylase deficiency late-onset , Late onset multiple carboxylase deficiency, HolMcarboxylase synthetase deficiency, 3-Methylcrotonyl-CoA carboxylase 2 deficiency. 3-Hydroxyisovaleric acid is also elevated in smokers, in subjects undergoing long-term anticonvulsant therapy with carbamazepine and/or phenytoin. These levels are elevated due to impairment of renal reclamation of biotin. Levels may also be increased from prolonged consumption of raw egg-whites (PMID: 16895887, 9523856, 15447901, 9176832)(OMIM: 210210, 253270, 600529, 253260, 246450, 210200, 238331) [HMDB]
CAS Number625-08-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-hydroxy-3-methyl-Butanoatehmdb
3-hydroxy-3-methyl-Butanoic acidhmdb
3-hydroxy-3-methyl-Butyric acidhmdb
3-Hydroxy-3-methylbutanoatehmdb
3-Hydroxy-3-methylbutanoic acidhmdb
3-Hydroxy-3-methylbutyratehmdb
3-Hydroxy-3-methylbutyric acidhmdb
3-Hydroxy-isovalerateGenerator
3-hydroxy-isovaleric acidhmdb
3-Hydroxyisovaleratehmdb
3-hydroxyisovaleric acidhmdb
3-OH-IsovalerateGenerator
3-OH-isovaleric acidhmdb
B-hydroxy-b-methylbutyratehmdb
B-hydroxy-b-methylbutyric acidhmdb
B-hydroxyisovaleratehmdb
B-hydroxyisovaleric acidhmdb
beta-hydroxy-beta-methylbutyratehmdb
beta-hydroxy-beta-methylbutyric acidhmdb
beta-hydroxyisovaleratehmdb
beta-hydroxyisovaleric acidhmdb
HMBChEBI
Hmb-D6ChEBI
β-hydroxy-β-methylbutyrateGenerator
β-hydroxy-β-methylbutyric acidGenerator
β-hydroxyisovalerateGenerator
β-hydroxyisovaleric acidGenerator
Chemical FormulaC5H10O3
IUPAC name3-hydroxy-3-methylbutanoic acid
InChI IdentifierInChI=1S/C5H10O3/c1-5(2,8)3-4(6)7/h8H,3H2,1-2H3,(H,6,7)
InChI KeyAXFYFNCPONWUHW-UHFFFAOYSA-N
Isomeric SMILESCC(C)(O)CC(O)=O
Average Molecular Weight118.1311
Monoisotopic Molecular Weight118.062994186
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentHydroxy fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Short-chain hydroxy acid
  • Hydroxy fatty acid
  • Branched fatty acid
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 6 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
MetaSci HMDB0000754
Tokyo Chemical Industry HMDB0000754
Toronto Research Chemicals H943605