ISOVALERIC ACID (CED0003975)

Record Information
Version1.0
Creation Date2016-05-19 02:11:32 UTC
Update Date2026-05-14 17:51:55 UTC
Accession NumberCHEM006235
Identification
Common NameISOVALERIC ACID
ClassSmall Molecule
Description
ISOVALERIC ACID belongs to the fatty acids and conjugates, a subclass of fatty acyls within the organic compounds. This compound has the chemical formula C5H10O2 and an average molecular weight of 102.13 g/mol. In industrial applications, it is utilized as a fragrance, as well as a flavouring and nutrient. The compound is found in or released from 40 recorded sources. These include household cleaning and consumer products such as bleaching agents, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. It is present in food, food processing, and cookware, specifically in food contact materials, cellar tools, food preservation, molasses and treatment of molasses, and fermentation processes for beer. Other sources include drinking water, indoor air, and electrical and electronic equipment, such as amplifiers, antennas, auxiliary devices, contacts, and conductors or conductive bodies characterised by the conductive materials. Regarding plastics, ISOVALERIC ACID is present in polypropylene and released in low-density polyethylene. Recorded exposure routes include oral, inhalation, and touch. Three protein targets have been recorded for this compound: 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase (cumD), aspartate aminotransferase (aspC), and sedolisin (pcp).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
3-Methyl-N-butyric acidChEBI
3-Methylbutanoic acidChEBI
3-MethylbuttersaeureChEBI
3-Methylbutyric acidChEBI
beta-Methylbutyric acidChEBI
Delphinic acidChEBI
Isobutylformic acidChEBI
Isopentanoic acidChEBI
Isopropylacetic acidChEBI
IsovalerateChEBI
Isovalerianic acidChEBI
IsovaleriansaeureChEBI
3-Methyl-N-butyrateGenerator
3-MethylbutanoateGenerator
3-MethylbutyrateGenerator
b-MethylbutyrateGenerator
b-Methylbutyric acidGenerator
beta-MethylbutyrateGenerator
Β-methylbutyrateGenerator
Β-methylbutyric acidGenerator
DelphinateGenerator
IsobutylformateGenerator
IsopentanoateGenerator
IsopropylacetateGenerator
IsovalerianateGenerator
3-Methyl butyric acidHMDB
3-Methylbutyric acid: isopropyl-acetateHMDB
3-Methylbutyric acid: isopropyl-acetic acidHMDB
3-Methyl-1-butanoic acidHMDB
Isovaleric acidKEGG
Chemical FormulaC5H10O2
Average Molecular Mass102.132 g/mol
Monoisotopic Mass102.068 g/mol
CAS Registry Number503-74-2
IUPAC Name3-methylbutanoic acid
Traditional Nameisovaleric acid
SMILESCC(C)CC(O)=O
InChI IdentifierInChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyGWYFCOCPABKNJV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility64.9 g/LALOGPS
logP1.26ALOGPS
logP1.21ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-052f-9000000000-2825512cee017b3ab87cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-059f-9200000000-628e11f1ffbaa913ef57Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gvo-9300000000-16b5d15d26810b72bb36Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-692791435c37fa74a692Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-b4c1b59653cd4d803637Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-9000000000-b0f7e399edb7f95572edNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03dl-9000000000-c8be68873f336c8de6d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-d0f20bc9813dcba79e8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-63b09019c280c88ee64dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-ef9ee29c1febd59e6a00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-d0f20bc9813dcba79e8bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-63b09019c280c88ee64dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-ef9ee29c1febd59e6a00Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-9000000000-871b21c20bba686fb915Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-1900000000-6ce72c7a41bfb4bc1b2dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0nmi-9300000000-efcb74e7796ba9769f97Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-9200000000-e825f0aa9ab54c1695d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-9ba126f982634fdc9406Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9000000000-afb863a56c8763c30251Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-8900000000-244535e4070d536a29b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pc0-9300000000-93ed2bc326380cb0d880Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-9000000000-44b2fa11a5a6daab8dd0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-9000000000-f59a47a684453302cbedNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-83176e54a19e36af76f2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-81052c8b00621fcf0443Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-4c159e60dacc58e6ba98Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ue9-7900000000-fd28737d49ed09628cfaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9000000000-b625e051bb477d2ece0dNot AvailableView Spectrum
MSMS Spectrumsplash10-03dl-9000000000-e7c77b2bc7f3ac5191e9Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2702.0Log mg/kg[1500:4800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
490Personal care & cosmeticsNot Available
494Food contact materialsFood, food processing & cookwareNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
512ContactsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
528MicrophonesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
543Cellar ToolsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
546Molasses And Treatment Of MolassesFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
567Tobacco Product CasesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
640Embroidering And TuftingTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
647Multicolour DyeingTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureGlutamate transporter homologO59010Pyrococcus horikoshii (strain ATCC 700860 / DSM 12428 / JCM 9974 /NBRC 100139 / OT-3)Predicted (SEA)1.08989
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P39086HumansPredicted (SEA)5.13805
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP04825Escherichia coli (strain K12)Predicted (SEA)1.40129
Click to view 3D structureBeta-lactamase VIM-1Q9XAY4Pseudomonas aeruginosaPredicted (SEA)1.08989
Peroxisome proliferator-activated receptor alpha structureClick to view 3D structurePeroxisome proliferator-activated receptor alphaQ07869HumansPredicted (SEA)269.436
Tyrosine-protein phosphatase non-receptor type 1 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 1P18031HumansPredicted (SEA)228.332
Click to view 3D structureAminopeptidase NP15145Sus scrofaPredicted (SEA)153.597
Lysine-specific demethylase 2A structureClick to view 3D structureLysine-specific demethylase 2AQ9Y2K7HumansPredicted (SEA)28.8821
Histone lysine demethylase PHF8 structureClick to view 3D structureHistone lysine demethylase PHF8Q9UPP1HumansPredicted (SEA)3.11397
Click to view 3D structureDihydroxyacetone phosphate acyltransferaseO15228HumansPredicted (SEA)16.4262
Peroxisome proliferator-activated receptor delta structureClick to view 3D structurePeroxisome proliferator-activated receptor deltaQ03181HumansPredicted (SEA)240.554
Click to view 3D structureMast cell carboxypeptidase AP15088HumansPredicted (SEA)43.4399
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)4.9045
Click to view 3D structureSodium- and chloride-dependent GABA transporter 2P31646Rattus norvegicusPredicted (SEA)2.64687
Click to view 3D structureSodium- and chloride-dependent creatine transporter 1P48029HumansPredicted (SEA)0.622794
Olfactory receptor 51E2 structureClick to view 3D structureOlfactory receptor 51E2Q9H255HumansPredicted (SEA)1.16774
Egl nine homolog 1 structureClick to view 3D structureEgl nine homolog 1Q9GZT9HumansPredicted (SEA)44.2184
Click to view 3D structureExcitatory amino acid transporter 3P51907Rattus norvegicusPredicted (SEA)0.622794
Click to view 3D structureSuccinate receptor 1Q99MT6Mus musculusPredicted (SEA)0.622794
SPRY domain-containing SOCS box protein 2 structureClick to view 3D structureSPRY domain-containing SOCS box protein 2Q99619HumansPredicted (SEA)38.3797
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP15144HumansPredicted (SEA)278.311
Click to view 3D structureCytosol aminopeptidaseP28838HumansPredicted (SEA)162.938
Click to view 3D structureNeprilysinQ61391Mus musculusPredicted (SEA)143.243
Click to view 3D structureProstaglandin G/H synthase 2P79208Ovis ariesPredicted (SEA)87.1133
Gamma-glutamyl hydrolase structureClick to view 3D structureGamma-glutamyl hydrolaseQ92820HumansPredicted (SEA)9.88685
Concentrations
Not Available
External Links
DrugBank IDDB03750
HMDB IDHMDB0000718
FooDB IDFDB001324
Phenol Explorer IDNot Available
KNApSAcK IDC00001189
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID109
PDB IDNot Available
Wikipedia Link3-Methylbutanoic acid
Chemspider ID10001
ChEBI ID28484
PubChem Compound ID10430
Kegg Compound IDC08262
YMDB IDYMDB01606
ECMDB IDECMDB00718
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12743728
2. Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp.
3. Hoffmann GF, von Kries R, Klose D, Lindner M, Schulze A, Muntau AC, Roschinger W, Liebl B, Mayatepek E, Roscher AA: Frequencies of inherited organic acidurias and disorders of mitochondrial fatty acid transport and oxidation in Germany. Eur J Pediatr. 2004 Feb;163(2):76-80. Epub 2004 Jan 9.
4. Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5.
5. Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8.
6. Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64.
7. Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5.