Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2019-11-26 02:58:47 UTC
Primary IDFDB003277
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Methylpropanoic acid
DescriptionPresent in apple, morello cherry, guava fruit, wine grapes, pineapple, crispbread, other breads, cheeses, wines, scallop and several essential oils, e.g. Roman chamomile. Acid and simple esters used as flavouring agents Isobutyric acid is a carboxylic or short chain fatty acid with characteristic sweat-like smell. Small amount of isobutyrate is generated via microbial (gut) metabolism. Small amounts may also be found in certain foods or fermented beverages. There is anosmia (genetic inability to smell) for the odor of isobutyric acid with a frequency of about 2.5%. (OMIM 207000). Isobutyric acid is slightly soluble in water but much more soluble in ethanol, ether and organic solvents. Isobutyric acid can affect people if breathed in and may be absorbed through the skin. Contact can irritate and burn the skin and eyes. Breathing Isobutyric acid can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.; Isobutyric acid is an isomer of n-butyric acid; they have the same chemical formula C4H8 O2 but a different structure.; Isobutyric acid, also known as 2-methylpropanoic acid, is a carboxylic acid with structural formula (CH3)2-CH-COOH. It is found in the free state in carobs (Ceratonia siliqua) and in the root of Arnica dulcis, and as an ethyl ester in croton oil.
CAS Number79-31-2
Structure
Thumb
Synonyms
SynonymSource
2,2-Dimethylacetic acidChEBI
2-METHYL-propionIC ACIDChEBI
2-MethylpropanoateChEBI
2-Methylpropanoic acidChEBI
2-MethylpropionsaeureChEBI
alpha-Isobutyric acidChEBI
alpha-Methylpropanoic acidChEBI
alpha-Methylpropionic acidChEBI
Dimethylacetic acidChEBI
Iso-butyric acidChEBI
Iso-C3H7COOHChEBI
IsobutanoateChEBI
Isobutanoic acidChEBI
IsobuttersaeureChEBI
IsobutyrateChEBI
Isopropylformic acidChEBI
2,2-DimethylacetateGenerator
2-METHYL-propionateGenerator
a-IsobutyrateGenerator
a-Isobutyric acidGenerator
alpha-IsobutyrateGenerator
Α-isobutyrateGenerator
Α-isobutyric acidGenerator
a-MethylpropanoateGenerator
a-Methylpropanoic acidGenerator
alpha-MethylpropanoateGenerator
Α-methylpropanoateGenerator
Α-methylpropanoic acidGenerator
a-MethylpropionateGenerator
a-Methylpropionic acidGenerator
alpha-MethylpropionateGenerator
Α-methylpropionateGenerator
Α-methylpropionic acidGenerator
DimethylacetateGenerator
Iso-butyrateGenerator
IsopropylformateGenerator
2-MethylpropionateHMDB
2-Methylpropionic acidHMDB
I-butyrateHMDB
I-butyric acidHMDB
Ammonium isobutyrateHMDB
Isobutyric acid, ammonium saltHMDB
Isobutyric acid, sodium saltHMDB
2-Methpropanoic acidHMDB
Isobutyric acid, hemiammoniateHMDB
Sodium isobutyrateHMDB
Isobutyric acid, calcium saltHMDB
Isobutyric acid, nickel saltHMDB
Isobutyric acid, potassium saltHMDB
Isobutyric acid, sodium salt, 11C-labeledHMDB
Isobutyric acid, sodium salt, 14C-labeledHMDB
Isobutyric acidKEGG
α-methylpropanoic acidbiospider
α-methylpropionic acidbiospider
1iupbiospider
2-METHYL-PROPIONIC ACIDbiospider
533-90-4 (calcium salt)biospider
A-methylpropanoatebiospider
A-methylpropanoic acidbiospider
A-methylpropionatebiospider
A-methylpropionic acidbiospider
Acetic acid, dimethyl-biospider
Alpha-methylpropanoatebiospider
Alpha-methylpropanoic acidbiospider
Alpha-methylpropionatebiospider
Alpha-methylpropionic acidbiospider
ALQbiospider
Cenex RP b2biospider
FEMA 2222db_source
ISBbiospider
iso-C3H7COOHbiospider
Isobutyric acid [UN2529] [Flammable liquid]biospider
Isobutyric acid, 8CIdb_source
Methylpropanoic acidbiospider
Methylpropanoic acid, 2-biospider
Methylpropionic acidbiospider
Propanoic acid, 2-methyl-biospider
Propionic acid, 2-methyl-biospider
Tenox EBP 2biospider
Tenox IBP-2biospider
Tenox IBP-2 Grain Prbiospider
Tenox IBP-2 Grain Pr.biospider
α-isobutyrateGenerator
α-isobutyric acidGenerator
α-methylpropanoateGenerator
α-methylpropanoic acidGenerator
α-methylpropionateGenerator
α-methylpropionic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility197 g/LALOGPS
logP0.78ALOGPS
logP1.02ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability9.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC4H8O2
IUPAC name2-methylpropanoic acid
InChI IdentifierInChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI KeyKQNPFQTWMSNSAP-UHFFFAOYSA-N
Isomeric SMILESCC(C)C(O)=O
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
Classification
Description Belongs to the class of organic compounds known as carboxylic acids. Carboxylic acids are compounds containing a carboxylic acid group with the formula -C(=O)OH.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acids
Direct ParentCarboxylic acids
Alternative Parents
Substituents
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 54.53%; H 9.15%; O 36.32%DFC
Melting PointFp -47°DFC
Boiling PointBp35 118-119°DFC
Experimental Water Solubility167 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP0.94SANGSTER (1993)
Experimental pKapKa 4.79 (4.85)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 0.95DFC
Refractive Indexn20D 1.3930DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e4785841363Spectrum
GC-MS2-Methylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4c977a2f823cde05363aSpectrum
GC-MS2-Methylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-e8e4dc7f7f3f492ec19cSpectrum
GC-MS2-Methylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-4c977a2f823cde05363aSpectrum
GC-MS2-Methylpropanoic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9000000000-e8e4dc7f7f3f492ec19cSpectrum
Predicted GC-MS2-Methylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a1Spectrum
Predicted GC-MS2-Methylpropanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d7535Spectrum
Predicted GC-MS2-Methylpropanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b614Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca2Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-688272ebde48c146c6d7Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-f1d1211c63775f704d72Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d5f9008f8738e9ee1206Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-af791f98a192fc352a65Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d5f9008f8738e9ee1206Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-af791f98a192fc352a65Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-b9f811f5e57b3eeeb842Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-eabd518990089acf84caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9ec563a3b4f50dc2aaafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-eee01af90e21c20eb584Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4952a01442de6ea6ecfeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-23cf7c0a08ac346b6bfeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rl-9000000000-7ca1184fbf16cfe0b735Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-4b3590a18d40d4d58a01Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-9000000000-97afb40e14188e82aee9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9000000000-82e9a26713840d90625eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-f007a4a376085ff3e56aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-17c0b668153fbfe212cbSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID6341
ChEMBL IDCHEMBL108778
KEGG Compound IDC02632
Pubchem Compound ID6590
Pubchem Substance IDNot Available
ChEBI ID16135
Phenol-Explorer IDNot Available
DrugBank IDDB02531
HMDB IDHMDB01873
CRC / DFC (Dictionary of Food Compounds) IDCVK55-C:CVK55-C
EAFUS ID1884
Dr. Duke ID2-METHYL-PROPIONIC-ACID|ISOBUTYRIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029462
HET IDALQ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID79-31-2
GoodScent IDrw1002281
SuperScent ID6590
Wikipedia IDIsobutyric 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
irritantDUKE
transdermalDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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
butter
  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
cheese
  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
strawberry
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
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).