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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:41:45 UTC
Update Date2022-03-07 02:52:53 UTC
HMDB IDHMDB0031231
Secondary Accession Numbers
  • HMDB31231
Metabolite Identification
Common Namexi-2-Ethyl-1-hexanol
Description2-Ethyl-1-hexanol, also known as 2-ethylhexyl alcohol, is a member of the class of compounds known as fatty alcohols. Fatty alcohols are aliphatic alcohols consisting of a chain of a least six carbon atoms. Thus, 2-ethyl-1-hexanol is considered to be a fatty alcohol lipid molecule. 2-ethyl-1-hexanol is practically insoluble in water. 2-Ethyl-1-hexanol can be found in a number of food items such as tea, cereals and cereal products, fats and oils, and alcoholic beverages. 2-Ethyl-1-hexanol exists in all eukaryotes, ranging from yeast to humans and in mammals it can be found primarily in feces and saliva.
Structure
Data?1563862098
Synonyms
ValueSource
2-Ethyl-1-hexanolChEBI
FEMA 3151HMDB
2-EthylhexanolHMDB
2-Ethylhexanol, titanium (4+) saltHMDB
Chemical FormulaC8H18O
Average Molecular Weight130.2279
Monoisotopic Molecular Weight130.135765198
IUPAC Name2-ethylhexan-1-ol
Traditional Name2-ethylhexanol
CAS Registry NumberNot Available
SMILES
CCCCC(CC)CO
InChI Identifier
InChI=1S/C8H18O/c1-3-5-6-8(4-2)7-9/h8-9H,3-7H2,1-2H3
InChI KeyYIWUKEYIRIRTPP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point-76.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point184.00 to 186.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1379 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.820 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP3.01ALOGPS
logP2.5ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)17.7ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.41 m³·mol⁻¹ChemAxon
Polarizability17.02 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]+128.77931661259
DarkChem[M-H]-126.7431661259
DeepCCS[M+H]+136.51330932474
DeepCCS[M-H]-134.47530932474
DeepCCS[M-2H]-170.18830932474
DeepCCS[M+Na]+144.92730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-2-Ethyl-1-hexanolCCCCC(CC)CO1464.1Standard polar33892256
xi-2-Ethyl-1-hexanolCCCCC(CC)CO1025.3Standard non polar33892256
xi-2-Ethyl-1-hexanolCCCCC(CC)CO1025.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
xi-2-Ethyl-1-hexanol,1TMS,isomer #1CCCCC(CC)CO[Si](C)(C)C1112.2Semi standard non polar33892256
xi-2-Ethyl-1-hexanol,1TBDMS,isomer #1CCCCC(CC)CO[Si](C)(C)C(C)(C)C1308.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4i-9000000000-51481f3434a1c33554d12017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4l-9000000000-95177f2f4a0e7724cc322017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4l-9000000000-4e3f8e8046c7b7f5b3c72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4i-9000000000-51481f3434a1c33554d12018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4l-9000000000-95177f2f4a0e7724cc322018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-2-Ethyl-1-hexanol EI-B (Non-derivatized)splash10-0a4l-9000000000-4e3f8e8046c7b7f5b3c72018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2-Ethyl-1-hexanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7i-9300000000-d11bf4a3d5099d688e592016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2-Ethyl-1-hexanol GC-MS (1 TMS) - 70eV, Positivesplash10-0fki-9600000000-cdc2bab14be7890de5642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-2-Ethyl-1-hexanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-9000000000-123187d57878f5d5685c2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 10V, Positive-QTOFsplash10-01q9-1900000000-413f50ae945f92e8e7ce2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 20V, Positive-QTOFsplash10-03di-7900000000-5ad439d4cfe105fdcc342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 40V, Positive-QTOFsplash10-052f-9000000000-14f105d41164651aafa12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 10V, Negative-QTOFsplash10-004i-1900000000-cc95d3a1f162ab01a5612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 20V, Negative-QTOFsplash10-004j-6900000000-50ed5309a17a142d20a52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 40V, Negative-QTOFsplash10-0002-9100000000-aff37524b5920128cd952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 10V, Positive-QTOFsplash10-0a4i-9000000000-edd190d70e0f296c14652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 20V, Positive-QTOFsplash10-0a4i-9000000000-9f823afed791fcff62002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 40V, Positive-QTOFsplash10-052f-9000000000-a85aa032524bf5562e962021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 10V, Negative-QTOFsplash10-004i-0900000000-aaa4ad827ef171a5b04a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 20V, Negative-QTOFsplash10-08i0-3900000000-b1b7216997d8960928c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-2-Ethyl-1-hexanol 40V, Negative-QTOFsplash10-0a4i-9300000000-96a0eb864d9930c4a8fd2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Breath
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease
details
SalivaDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothCeliac disease 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 ]
  2. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Celiac disease
  1. Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003255
KNApSAcK IDC00050413
Chemspider ID7434
KEGG Compound IDC02498
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Ethylhexanol
METLIN IDNot Available
PubChem Compound7720
PDB IDNot Available
ChEBI ID16011
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015291
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.