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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-12 01:44:49 UTC
Update Date2022-03-07 02:56:30 UTC
HMDB IDHMDB0040209
Secondary Accession Numbers
  • HMDB40209
Metabolite Identification
Common NameEthyl hexanoate
DescriptionEthyl hexanoate, also known as ethyl caproate or ethyl hexoic acid, is a fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol. It has a role as a metabolite. It is a fatty acid ethyl ester and a hexanoate ester. Ethyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Ethyl hexanoate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1563863506
Synonyms
ValueSource
Caproic acid ethyl esterChEBI
Ethyl caproateChEBI
Ethyl ester OF hexanoic acidChEBI
Ethyl hexoateChEBI
Ethyl N-hexanoatChEBI
Hexanoic acid ethyl esterChEBI
N-Caproic acid ethyl esterChEBI
Caproate ethyl esterGenerator
Ethyl caproic acidGenerator
Ethyl ester OF hexanoateGenerator
Ethyl hexoic acidGenerator
Hexanoate ethyl esterGenerator
N-Caproate ethyl esterGenerator
Ethyl hexanoic acidGenerator
Acetic acid, butyl-, ethyl esterHMDB
Caproic acid ethylesterHMDB
Capronic ether absoluteHMDB
Ethyl butyl acetateHMDB
Ethyl butyl acetate (dot)HMDB
Ethyl hexanoate (caproate)HMDB
Ethyl N-hexanoateHMDB
FEMA 2439HMDB
Hexanoic acid, ethyl esterHMDB
Hexanoic acid, ethyl ester, mixt. with soybean oil epoxideHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Nameethyl hexanoate
Traditional Nameethyl hexanoate
CAS Registry Number123-66-0
SMILES
CCCCCC(=O)OCC
InChI Identifier
InChI=1S/C8H16O2/c1-3-5-6-7-8(9)10-4-2/h3-7H2,1-2H3
InChI KeySHZIWNPUGXLXDT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • 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

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-67.5 °CNot Available
Boiling Point166.00 to 168.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.63 mg/mL at 25 °CNot Available
LogP2.823 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP2.92ALOGPS
logP2.31ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.59 m³·mol⁻¹ChemAxon
Polarizability17.32 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.68331661259
DarkChem[M-H]-130.731661259
DeepCCS[M+H]+138.52630932474
DeepCCS[M-H]-136.52730932474
DeepCCS[M-2H]-172.59930932474
DeepCCS[M+Na]+147.27830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl hexanoateCCCCCC(=O)OCC1225.7Standard polar33892256
Ethyl hexanoateCCCCCC(=O)OCC986.8Standard non polar33892256
Ethyl hexanoateCCCCCC(=O)OCC1022.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl hexanoate EI-B (Non-derivatized)splash10-01rl-9000000000-c4a428f4af3678af55b52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl hexanoate EI-B (Non-derivatized)splash10-01tl-9000000000-b511103509087502c6df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl hexanoate EI-B (Non-derivatized)splash10-01rl-9000000000-c4a428f4af3678af55b52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl hexanoate EI-B (Non-derivatized)splash10-01tl-9000000000-b511103509087502c6df2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl hexanoate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-9000000000-3f4b554f930a16c91f852016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl hexanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 10V, Positive-QTOFsplash10-0002-5900000000-1d6e0542ed766431edd92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 20V, Positive-QTOFsplash10-0002-9200000000-ea176c85160cde938be42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 40V, Positive-QTOFsplash10-0a4l-9000000000-f08ba8bdf4f45654e5e12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 10V, Negative-QTOFsplash10-0007-7900000000-58755a27868e3915af732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 20V, Negative-QTOFsplash10-0002-9300000000-c8e3af4a4f844e662a582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 40V, Negative-QTOFsplash10-0005-9000000000-a50363e5c24481fa9a2d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 10V, Negative-QTOFsplash10-0002-9000000000-f273dbe7b19bad8e99102021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 20V, Negative-QTOFsplash10-004j-9000000000-c688f81973ea98568c642021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 40V, Negative-QTOFsplash10-052b-9000000000-7e778dcba6da2ac098b22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 10V, Positive-QTOFsplash10-00r7-9100000000-4e527c99ae1b67a09e912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 20V, Positive-QTOFsplash10-05fu-9000000000-26df2f6eb35fbbfa03c72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl hexanoate 40V, Positive-QTOFsplash10-0007-9000000000-b6c469234b2e28e58a212021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
Associated Disorders and Diseases
Disease References
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 IDFDB019921
KNApSAcK IDC00035612
Chemspider ID29005
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl hexanoate
METLIN IDNot Available
PubChem Compound31265
PDB IDNot Available
ChEBI ID86055
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1004811
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.