Back to Compounds

3-Methylbutanoic acid (FDB001324)

Record Information
Version1.0
Creation date2010-04-08 22:04:55 UTC
Update date2019-11-26 02:56:19 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
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03dl-9000000000-e7c77b2bc7f3ac5191e92015-03-01View Spectrum
GC-MS3-Methylbutanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfSpectrum
GC-MS3-Methylbutanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Spectrum
GC-MS3-Methylbutanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-9e19eb5f5137b78591dfSpectrum
GC-MS3-Methylbutanoic acid, non-derivatized, GC-MS Spectrumsplash10-03dl-9000000000-43967f1315b6b575f330Spectrum
Predicted GC-MS3-Methylbutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9000000000-2825512cee017b3ab87cSpectrum
Predicted GC-MS3-Methylbutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-059f-9200000000-628e11f1ffbaa913ef57Spectrum
Predicted GC-MS3-Methylbutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methylbutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS3-Methylbutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0gvo-9300000000-16b5d15d26810b72bb362012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-692791435c37fa74a6922012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b4c1b59653cd4d8036372012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-03dl-9000000000-b0f7e399edb7f95572ed2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03dl-9000000000-c8be68873f336c8de6d62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-63b09019c280c88ee64d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a002012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-d0f20bc9813dcba79e8b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-63b09019c280c88ee64d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-1900000000-ef9ee29c1febd59e6a002017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-871b21c20bba686fb9152021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-6ce72c7a41bfb4bc1b2d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0nmi-9300000000-efcb74e7796ba9769f972021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-e825f0aa9ab54c1695d32015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-9000000000-9ba126f982634fdc94062015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-afb863a56c8763c302512015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-244535e4070d536a29b32015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9300000000-93ed2bc326380cb0d8802015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-44b2fa11a5a6daab8dd02015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9000000000-f59a47a684453302cbed2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-83176e54a19e36af76f22021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-81052c8b00621fcf04432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-4c159e60dacc58e6ba982021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-7900000000-fd28737d49ed09628cfa2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).