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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:56:36 UTC
Update Date2019-07-23 07:17:23 UTC
HMDB IDHMDB0061886
Secondary Accession Numbers
  • HMDB61886
Metabolite Identification
Common Name2-Hexanol
Description2-Hexanol, also known as hexan-2-ol, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl). Thus, 2-hexanol is considered to be a fatty alcohol lipid molecule. 2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. 2-Hexanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Hexanol is a chemical and winey tasting compound. Outside of the human body, 2-Hexanol is found, on average, in the highest concentration within safflowers. 2-Hexanol has also been detected, but not quantified in, several different foods, such as pepper (c. frutescens), tea, green bell peppers, corns, and orange bell peppers. This could make 2-hexanol a potential biomarker for the consumption of these foods. 2-Hexanol, with regard to humans, has been linked to the inborn metabolic disorder celiac disease. It is an isomer of the other hexanols. 2-Hexanol has a chiral center and can be resolved into enantiomers.
Structure
Data?1563866243
Synonyms
ValueSource
Hexan-2-olHMDB
Chemical FormulaC6H14O
Average Molecular Weight102.1748
Monoisotopic Molecular Weight102.10446507
IUPAC Namehexan-2-ol
Traditional Name2-hexanol
CAS Registry NumberNot Available
SMILES
CCCCC(C)O
InChI Identifier
InChI=1S/C6H14O/c1-3-4-5-6(2)7/h6-7H,3-5H2,1-2H3
InChI KeyQNVRIHYSUZMSGM-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.2 g/LALOGPS
logP1.75ALOGPS
logP1.67ChemAxon
logS-0.77ALOGPS
pKa (Strongest Acidic)17.68ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.15 m³·mol⁻¹ChemAxon
Polarizability13.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-d2359b7e811b8b064741Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052g-9000000000-5ed68fbbaa3fc418b8c9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-4c27b69e9102343f0cbaSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-6a2465fd6b8f6d61c645Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-13cf4a6ddf1472a5e7afSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-025559fc240ab827b146Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-d2359b7e811b8b064741Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052g-9000000000-5ed68fbbaa3fc418b8c9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-4c27b69e9102343f0cbaSpectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-000i-9000000000-6a2465fd6b8f6d61c645Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-13cf4a6ddf1472a5e7afSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-9000000000-025559fc240ab827b146Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-9000000000-52e19fa4c4bcd06646a6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-06g3-9500000000-b66c1dd8ded5f6316d10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-9200000000-721b46c83f2085e83494Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9100000000-084ab1dd479565a37a5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-fa8209fe0c9c5bbe8d15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-2900000000-1f6dc02c43b345b910edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ue9-8900000000-91731673e906063261b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9000000000-91d8c1ca99e3b966a532Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-0ebe978c5d40bd72e235Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Children (1-13 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Children (1-13 years old)BothCeliac disease details
Associated Disorders and Diseases
Disease References
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
FoodDB IDFDB004514
KNApSAcK IDNot Available
Chemspider ID11794
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Hexanol
METLIN IDNot Available
PubChem Compound12297
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Perbellini L, De Grandis D, Semenzato F, Rizzuto N, Simonati A: An experimental study on the neurotoxicity of n-hexane metabolites: hexanol-1 and hexanol-2. Toxicol Appl Pharmacol. 1978 Nov;46(2):421-7. [PubMed:734671 ]
  2. Yoshida Y, Liu J, Sugiura T, Ishidao T, Ueno S, Yanagita H, Fueta Y, Kunugita N, Hori H, Yamashita U: The indoor air pollutant 2-ethyl-hexanol activates CD4 cells. Chem Biol Interact. 2009 Jan 27;177(2):137-41. doi: 10.1016/j.cbi.2008.10.053. Epub 2008 Nov 6. [PubMed:19038237 ]
  3. Gallego-Iniesta Garcia MP, Moreno Sanroma A, Martin Porrero MP, Tapia Valle A, Cabanas Galan B, Salgado Munoz MS: Reactivity of 2-ethyl-1-hexanol in the atmosphere. Phys Chem Chem Phys. 2010 Apr 7;12(13):3294-300. doi: 10.1039/b923899a. Epub 2010 Feb 19. [PubMed:20237722 ]
  4. McGinty D, Scognamiglio J, Letizia CS, Api AM: Fragrance material review on 2-ethyl-1-hexanol. Food Chem Toxicol. 2010 Jul;48 Suppl 4:S115-29. doi: 10.1016/j.fct.2010.05.042. [PubMed:20659633 ]
  5. Wikipedia [Link]
  6. Scott A. Stevenson, Wugeng Liang, 'INTEGRATED PLANT FOR PRODUCING 2-ETHYL-HEXANOL AND METHACRYLIC ACID.' U.S. Patent US20100260647, issued October 14, 2010. [Link]