Record Information
Version1.0
Creation date2010-04-08 22:05:44 UTC
Update date2015-10-09 22:31:16 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
α-methylpropanoic acidbiospider
α-methylpropionic acidbiospider
1iupbiospider
2-METHYL-propionateGenerator
2-METHYL-PROPIONIC ACIDbiospider
2-Methylpropanoatebiospider
2-Methylpropionatebiospider
2-Methylpropionic acidbiospider
2-MethylpropionsaeureChEBI
2,2-DimethylacetateGenerator
2,2-Dimethylacetic acidChEBI
533-90-4 (calcium salt)biospider
a-IsobutyrateGenerator
a-Isobutyric acidGenerator
A-methylpropanoatebiospider
A-methylpropanoic acidbiospider
A-methylpropionatebiospider
A-methylpropionic acidbiospider
Acetic acid, dimethyl-biospider
alpha-IsobutyrateGenerator
alpha-Isobutyric acidChEBI
Alpha-methylpropanoatebiospider
Alpha-methylpropanoic acidbiospider
Alpha-methylpropionatebiospider
Alpha-methylpropionic acidbiospider
ALQbiospider
Cenex RP b2biospider
Dimethylacetatebiospider
Dimethylacetic acidbiospider
FEMA 2222db_source
I-butyratebiospider
I-butyric acidbiospider
ISBbiospider
Iso-butyratebiospider
Iso-butyric acidbiospider
iso-C3H7COOHbiospider
Isobutanoatebiospider
Isobutanoic acidbiospider
IsobuttersaeureChEBI
Isobutyratebiospider
Isobutyric acidbiospider
Isobutyric acid [UN2529] [Flammable liquid]biospider
Isobutyric acid, 8CIdb_source
Isopropylformatebiospider
Isopropylformic acidbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound belongs to the class of organic compounds known as carboxylic acids. These 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
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-4c977a2f823cde05363aView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9000000000-e8e4dc7f7f3f492ec19cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d3c10d617448ce79a5a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9100000000-80d574b59e1edc9d7535View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00dr-9000000000-67f1d07ca106199c76d3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-d5e7b5664f34e843b614View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f79-9200000000-b18c55d6aa937214dca2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0006-9000000000-688272ebde48c146c6d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9000000000-f1d1211c63775f704d72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-d5f9008f8738e9ee1206View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-af791f98a192fc352a65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-d5f9008f8738e9ee1206View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-3b1bc720943b7b4b9b7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-af791f98a192fc352a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9000000000-eabd518990089acf84caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-9ec563a3b4f50dc2aaafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-eee01af90e21c20eb584View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-4952a01442de6ea6ecfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-23cf7c0a08ac346b6bfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00rl-9000000000-7ca1184fbf16cfe0b735View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e4785841363View in MoNA
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 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
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).