Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2018-05-28 22:10:18 UTC
Primary IDFDB001324
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Methylbutanoic acid
DescriptionFlavouring agent. Simple esters are used in flavourings. Constituent of hops, cheese etc.; an important component of cheese aroma and flavour 3-Methylbutanoic acid, or more commonly isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but extremely soluble in most common organic solvents.; Isovaleric acid has a strong pungent cheesy or sweaty smell, but its volatile esters have pleasing scents and are used widely in perfumery. It has been proposed that it is the anticonvulsant agent in valerian. It is a major component of the cause of unpleasant foot odor.; Isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents.; It has been suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor in prolonged gestation in the population of the Faroe Islands.; Previous studies suggested that was due to the high intake of n-3 polyunsaturated fatty acids has been, but fatty acid data for eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA) in blood lipids of Faroese and Norwegians was reviewed in terms of the type of fish eaten (mostly lean white fish with DHA much greater than EPA); the popular lean fish, thus, probably provides too little EPA to produce a marked effect on human biochemistry. (PMID 2646392).
CAS Number503-74-2
Structure
Thumb
Synonyms
SynonymSource
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
Isovaleric acidKEGG
β-methylbutyric acidbiospider
3-methyl-butanoic acidbiospider
3-Methyl-n-butyratebiospider
3-Methyl-n-butyric acidbiospider
3-methylbutanoic acid (isovaleric acid)biospider
3-Methylbutyric acid: isopropyl-Acetatebiospider
3-Methylbutyric acid: isopropyl-Acetic acidbiospider
3,4-Diisovaleryl adrenalinebiospider
B-methylbutyratebiospider
B-methylbutyric acidbiospider
Baldrianic aciddb_source
Beta-methylbutyratebiospider
Beta-methylbutyric acidbiospider
Butanoic acid, 3-methyl-, (R)-biospider
FEMA 3102db_source
iso-C4H9COOHbiospider
Isobutyl formic acidbiospider
Isovaleric acid sodium saltbiospider
IVAbiospider
Methylbutanoic acidbiospider
Phocenic aciddb_source
Viburnum aciddb_source
β-methylbutyrateGenerator
β-methylbutyric acidGenerator
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H10O2
IUPAC name3-methylbutanoic acid
InChI IdentifierInChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)
InChI KeyGWYFCOCPABKNJV-UHFFFAOYSA-N
Isomeric SMILESCC(C)CC(O)=O
Average Molecular Weight102.1317
Monoisotopic Molecular Weight102.068079564
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 58.80%; H 9.87%; O 31.33%DFC
Melting PointMp -37.6°DFC
Boiling PointBp 176.7° (183°)DFC
Experimental Water Solubility40.7 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.16HANSCH,C ET AL. (1995)
Experimental pKapKa 4.8DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd184 0.93DFC
Refractive Indexn15D 1.4064DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-9e19eb5f5137b78591dfView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03dl-9000000000-43967f1315b6b575f330View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-9000000000-2825512cee017b3ab87cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-059f-9200000000-628e11f1ffbaa913ef57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0gvo-9300000000-16b5d15d26810b72bb36View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-692791435c37fa74a692View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b4c1b59653cd4d803637View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b0f7e399edb7f95572edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-c8be68873f336c8de6d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-63b09019c280c88ee64dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-63b09019c280c88ee64dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e825f0aa9ab54c1695d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-9ba126f982634fdc9406View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-afb863a56c8763c30251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-244535e4070d536a29b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9300000000-93ed2bc326380cb0d880View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-44b2fa11a5a6daab8dd0View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10001
ChEMBL IDCHEMBL568737
KEGG Compound IDC08262
Pubchem Compound ID10430
Pubchem Substance IDNot Available
ChEBI ID28484
Phenol-Explorer IDNot Available
DrugBank IDDB03750
HMDB IDHMDB00718
CRC / DFC (Dictionary of Food Compounds) IDBZM14-Q:BZM14-Q
EAFUS ID1946
Dr. Duke IDISOVALERIANIC-ACID|ISOVALERIC-ACID|3-METHYL-BUTYRIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001189
HET IDIVA
Flavornet ID503-74-2
GoodScent IDrw1056411
SuperScent ID10430
Wikipedia IDIsovaleric acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
irritantDUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
sedative35717 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.DUKE
tranquilizerDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweat
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
acid
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
rancid
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
animal
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sour
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
stinky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
feet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweaty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cheese
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).