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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:41:44 UTC
Update Date2019-07-23 06:08:18 UTC
HMDB IDHMDB0031230
Secondary Accession Numbers
  • HMDB0062546
  • HMDB31230
  • HMDB62546
Metabolite Identification
Common Name2-Ethylhexanoic acid
Description2-Ethylhexanoic acid, also known as 2-ethylhexanoate or alpha-ethylcaproic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. 2-Ethylhexanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Ethylhexanoic acid is a potentially toxic compound.
Structure
Data?1563862098
Synonyms
ValueSource
2-EthylhexanoateGenerator
(+/-)-2-ethylhexanoIC ACIDHMDB
2-Butylbutanoic acidHMDB
2-Ethyl hexanoic acidHMDB
2-Ethyl-1-hexanoic acidHMDB
2-Ethyl-hexoic acidHMDB
2-Ethyl-hexonic acidHMDB
2-Ethylcaproic acidHMDB
2-Ethylcapronic acidHMDB
2-Ethylhexoic acidHMDB
3-Heptanecarboxylic acidHMDB
alpha-Ethylcaproic acidHMDB
alpha-Ethylhexanoic acidHMDB
Butylethylacetic acidHMDB
Sinesto bHMDB
a-Ethyl caproateGenerator
a-Ethyl caproic acidGenerator
alpha-Ethyl caproateGenerator
Α-ethyl caproateGenerator
Α-ethyl caproic acidGenerator
2-Ethylhexanoic acidMeSH
(±)-2-Ethylhexanoic acidHMDB
Ethylhexanoic acidHMDB
Octylic acidHMDB
α-Ethylcaproic acidHMDB
α-Ethylhexanoic acidHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Name2-ethylhexanoic acid
Traditional Name2-ethylhexanoic acid
CAS Registry Number149-57-5
SMILES
CCCCC(CC)C(O)=O
InChI Identifier
InChI=1S/C8H16O2/c1-3-5-6-7(4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)
InChI KeyOBETXYAYXDNJHR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility2 mg/mL at 20 °CNot Available
LogP2.64Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.07 g/LALOGPS
logP2.61ALOGPS
logP2.8ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)5.14ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.25 m³·mol⁻¹ChemAxon
Polarizability16.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0fb9-3920000000-7e7fbb23d9bdc5a56044Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-9000000000-ad0258cbd5d18520beb9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9300000000-2e3084f5a49e5800b8deSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i9-9200000000-e7de4220461eedb062f6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3900000000-66559dd7e31088c2bff8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052b-9400000000-2df69b4ff55243bf2d73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-238efca128749a9ad743Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4900000000-01f3d55a8d9b84636f29Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-9400000000-dec78c38085ece33408fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-9100000000-1e624a8a74aa0be27fb5Spectrum
MSMass Spectrum (Electron Ionization)splash10-059i-9000000000-8e486671e74560231b2aSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Sweat
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified254.256 (0-4345.472) nmol/g wet fecesChildren (1 - 13 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected and Quantified46.228 (0-416.0559) nmol/g wet fecesChildren (1 - 13 years old)Both
Autism
details
FecesDetected and Quantified115.571 (0-808.998) nmol/g wet fecesChildren (1 - 13 years old)Both
Developmental Disorder Not Otherwise Specified
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003254
KNApSAcK IDC00007414
Chemspider ID8373
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Ethylhexanoic acid
METLIN IDNot Available
PubChem Compound8697
PDB IDNot Available
ChEBI ID89058
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.