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Record Information
Version3.6
Creation Date2006-02-23 12:29:19 UTC
Update Date2016-08-17 21:42:06 UTC
HMDB IDHMDB01873
Secondary Accession Numbers
  • HMDB03151
Metabolite Identification
Common NameIsobutyric acid
DescriptionIsobutyric 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.
Structure
Thumb
Synonyms
ValueSource
2-Methylpropanoic acidKegg
IsobutanoateKegg
Dimethylacetic acidKegg
IsobutyrateKegg
2-MethylpropanoateGenerator
Isobutanoic acidGenerator
DimethylacetateGenerator
2-MethylpropionateHMDB
2-Methylpropionic acidHMDB
a-MethylpropanoateHMDB
a-Methylpropanoic acidHMDB
a-MethylpropionateHMDB
a-Methylpropionic acidHMDB
alpha-MethylpropanoateHMDB
alpha-Methylpropanoic acidHMDB
alpha-MethylpropionateHMDB
alpha-Methylpropionic acidHMDB
I-butyrateHMDB
I-butyric acidHMDB
iso-ButyrateHMDB
iso-Butyric acidHMDB
IsopropylformateHMDB
Isopropylformic acidHMDB
Chemical FormulaC4H8O2
Average Molecular Weight88.1051
Monoisotopic Molecular Weight88.0524295
IUPAC Name2-methylpropanoic acid
Traditional Nameisobutyric acid
CAS Registry Number79-31-2
SMILES
CC(C)C(O)=O
InChI Identifier
InChI=1S/C4H8O2/c1-3(2)4(5)6/h3H,1-2H3,(H,5,6)
InChI KeyInChIKey=KQNPFQTWMSNSAP-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility167 mg/mL at 20 °CNot Available
LogP0.94SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility197.0 mg/mLALOGPS
logP0.78ALOGPS
logP1.02ChemAxon
logS0.35ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.85 m3·mol-1ChemAxon
Polarizability9.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0006-9000000000-ce74765d5e4785841363View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Fibroblasts
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.7-4.4) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.8 (0-3.6) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1710 +/- 1050 nmol/g of fecesAdult (>18 years old)Female
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified0 - 6.87 ppmChildren (1-13 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified116.73 +/- 107.44 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
SalivaDetected and Quantified885.0 (10.0-1760.0) uMAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
UrineDetected and Quantified2.929 +/- 1.157 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified3.9 umol/mmol creatinineAdult (>18 years old)Not Specified
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified2.82 umol/mmol creatinineAdult (>18 years old)Male
Normal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified15.0 (12.0-27.0) umol/mmol creatinineInfant (0-1 year old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified39.0 (9.0-122.0) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified3.5 (1.2-9.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)MaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified8.4 +/- 1.9 uMAdult (>18 years old)BothHeart Transplant details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified0 - 21.80 ppmChildren (1-13 years old)Not Specified
Treated celiac disease
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified2.44 +/- 1.584 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02531
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003277
KNApSAcK IDC00029462
Chemspider ID6341
KEGG Compound IDC02632
BioCyc IDISOBUTANOATE
BiGG IDNot Available
Wikipedia LinkIsobutyric acid
NuGOwiki LinkHMDB01873
Metagene LinkHMDB01873
METLIN ID106
PubChem Compound6590
PDB IDALQ
ChEBI ID16135
References
Synthesis ReferenceWang, Hengxiu; Chen, Weibin; Zhao, Dehua; Zhang, Jianbin. Preparation of isobutyric acid. Faming Zhuanli Shenqing Gongkai Shuomingshu (2003), 5 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
  2. Hoverstad T, Fausa O, Bjorneklett A, Bohmer T: Short-chain fatty acids in the normal human feces. Scand J Gastroenterol. 1984 May;19(3):375-81. [6740214 ]
  3. Mix KS, Coon CI, Rosen ED, Suh N, Sporn MB, Brinckerhoff CE: Peroxisome proliferator-activated receptor-gamma-independent repression of collagenase gene expression by 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid and prostaglandin 15-deoxy-delta(12,14) J2: a role for Smad signaling. Mol Pharmacol. 2004 Feb;65(2):309-18. [14742672 ]
  4. Faed EM, McQueen EG: Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clin Exp Pharmacol Physiol. 1978 Mar-Apr;5(2):195-8. [648038 ]