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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-12-23 16:50:59 UTC
Update Date2021-10-13 05:29:14 UTC
HMDB IDHMDB0011469
Secondary Accession Numbers
  • HMDB11469
Metabolite Identification
Common Name2-Butanol
Description2-Butanol, also known as 2-butyl alcohol or 2-hydroxybutane, 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). 2-Butanol is an odorless tasting compound. Based on a literature review very few articles have been published on 2-Butanol.
Structure
Data?1582752908
Synonyms
ValueSource
1-Methyl-1-propanolChEBI
1-Methylpropyl alcoholChEBI
2-Butyl alcoholChEBI
2-HydroxybutaneChEBI
Butanol-2ChEBI
MethylethylcarbinolChEBI
S-Butyl alcoholChEBI
S-ButylalkoholChEBI
Sec-butanolChEBI
Sec-butyl alcoholChEBI
2-ButanolChEBI
2-Butanol, (+)-isomerMeSH, HMDB
2-Butanol, (-)-isomerMeSH, HMDB
2-Butanol, lithium salt, (S)-isomerMeSH, HMDB
2-Butanol, aluminum saltMeSH, HMDB
2-Butanol, lithium salt, (R)-isomerMeSH, HMDB
2-Butanol, (+-)-isomerMeSH, HMDB
2-Butanol, lithium salt, (+-)-isomerMeSH, HMDB
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Namebutan-2-ol
Traditional Name2-butanol
CAS Registry Number78-92-2
SMILES
CCC(C)O
InChI Identifier
InChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
InChI KeyBTANRVKWQNVYAZ-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
Physiological effect
Disposition
Biological locationRoute of exposureSource
Process
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-114.7 °CNot Available
Boiling Point99.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility181 mg/mL at 25 °CNot Available
LogP0.61HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility195 g/LALOGPS
logP0.66ALOGPS
logP0.78ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity21.95 m³·mol⁻¹ChemAxon
Polarizability9.07 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]+113.55731661259
DarkChem[M-H]-106.5831661259
DeepCCS[M+H]+125.53430932474
DeepCCS[M-H]-123.63930932474
DeepCCS[M-2H]-159.28830932474
DeepCCS[M+Na]+133.73830932474
AllCCS[M+H]+122.032859911
AllCCS[M+H-H2O]+117.532859911
AllCCS[M+NH4]+126.232859911
AllCCS[M+Na]+127.432859911
AllCCS[M-H]-134.532859911
AllCCS[M+Na-2H]-140.132859911
AllCCS[M+HCOO]-146.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-ButanolCCC(C)O981.7Standard polar33892256
2-ButanolCCC(C)O570.1Standard non polar33892256
2-ButanolCCC(C)O594.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Butanol,1TMS,isomer #1CCC(C)O[Si](C)(C)C770.4Semi standard non polar33892256
2-Butanol,1TBDMS,isomer #1CCC(C)O[Si](C)(C)C(C)(C)C969.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-69a1867b969261fbdf062017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-ccad0f1d1aa3a22b166d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-ef7cd62aa636fe20c0eb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-69a1867b969261fbdf062018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-ccad0f1d1aa3a22b166d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Butanol EI-B (Non-derivatized)splash10-0002-9000000000-ef7cd62aa636fe20c0eb2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Butanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-056r-9000000000-88d60fe7c83e554404552017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Butanol GC-MS (1 TMS) - 70eV, Positivesplash10-00wi-9300000000-cb203a619c04be21a1202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Butanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-771b68c9e84f9101ec6d2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 10V, Positive-QTOFsplash10-0a4i-9000000000-4e78283c55f36c9feda22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 20V, Positive-QTOFsplash10-0a4i-9000000000-c325f8fdffc2a59e1d102015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 40V, Positive-QTOFsplash10-0a4i-9000000000-18f52ab5703ab9a7a1b02015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 10V, Negative-QTOFsplash10-00di-9000000000-de5df4899287d1e83d602015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 20V, Negative-QTOFsplash10-05fr-9000000000-920e6cee03b9b4c5fb072015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 40V, Negative-QTOFsplash10-0a4i-9000000000-fab3878f8110affe65c22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 10V, Negative-QTOFsplash10-00di-9000000000-4256cf8850659dacd1592021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 20V, Negative-QTOFsplash10-00di-9000000000-196f07d2f495373b81ea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 40V, Negative-QTOFsplash10-0a4i-9000000000-2e44988393496e99b51f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 10V, Positive-QTOFsplash10-0a4i-9000000000-2aeeb231544bed908c5f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 20V, Positive-QTOFsplash10-0a4i-9000000000-9d972b42b1bf6cc3b0d82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Butanol 40V, Positive-QTOFsplash10-052f-9000000000-0a72cbd1fb3863ce68eb2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified313.0 (54.0-863.0) uMAdult (>18 years old)BothAlcohol intoxication details
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)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Diarrhea-predominant IBS
details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. [PubMed:2779169 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016802
KNApSAcK IDC00053987
Chemspider ID6320
KEGG Compound IDNot Available
BioCyc IDCPD-326
BiGG IDNot Available
Wikipedia Link2-butanol
METLIN IDNot Available
PubChem Compound6568
PDB IDNot Available
ChEBI ID35687
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available