1-Butanol (YMDB01386)

Identification
YMDB IDYMDB01386
Name1-Butanol
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description3-Methyl-1-propanol (n-Butanol or n-butyl alcohol or normal butanol) is a primary alcohol with a 4-carbon structure and the molecular formula C4H9OH. Its isomers include isobutanol, 2-butanol, and tert-butanol. Butanol is one of the group of "fusel alcohols" (from the German for "bad liquor"), which have more than two carbon atoms and have significant solubility in water. n-Butanol occurs naturally as a minor product of the fermentation of sugars and other carbohydrates, and is present in many foods and beverages. It is also a permitted artificial flavorant in the United States, used in butter, cream, fruit, rum, whiskey, ice cream and ices, candy, baked goods and cordials. It is responsible for a potato-like aroma. [Wikipedia]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-Butanol
  • 1-Butyl alcohol
  • 1-Hydroxybutane
  • 3-Methyl-1-propanol
  • Alcool butylique
  • BuOH
  • Butan-1-ol
  • Butanol
  • Butanol-1
  • Butanolen
  • Butanolo
  • Butyl alcohol
  • Butyl hydroxide
  • Butylowy alkohol
  • Butyric alcohol
  • Hemostyp
  • Methylolpropane
  • n-Butan-1-ol
  • n-Butanol
  • n-Butanolbutanolen
  • n-Butyl alcohol
  • n-Butylalkohol
  • n-C4H9OH
  • NBA
  • propyl carbinol
  • Propylcarbinol
  • Propylmethanol
  • Alcohol, N-butyl
  • N Butyl alcohol
  • Alcohol, butyl
  • 1 Butanol
  • N Butanol
CAS number71-36-3
WeightAverage: 74.1216
Monoisotopic: 74.073164942
InChI KeyLRHPLDYGYMQRHN-UHFFFAOYSA-N
InChIInChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
IUPAC Namebutan-1-ol
Traditional IUPAC Namebutanol
Chemical FormulaC4H10O
SMILESCCCCO
Chemical Taxonomy
Description belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentPrimary alcohols
Alternative Parents
Substituents
  • Hydrocarbon derivative
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Charge0
Melting point-89.8 °C
Experimental Properties
PropertyValueReference
Water Solubility63.2 mg/mL at 25 oC [TEWARI,YB et al. (1982)]PhysProp
LogP0.88 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility158 g/LALOGPS
logP0.84ALOGPS
logP0.81ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.13 m³·mol⁻¹ChemAxon
Polarizability9.21 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
BalsamFDB031032
FruitFDB031032
FuselFDB031032
MedicinalFDB031032
MedicineFDB031032
OilFDB031032
SweetFDB031032
VanillaFDB031032
SMPDB PathwaysNot Available
KEGG Pathways
Butanoate metabolismec00650 Map00650
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-f8337e5e053a4d17e4edJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-610cf73e0b514e180dbdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9000000000-7e23cd40dde01cb89b6fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-f8337e5e053a4d17e4edJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-610cf73e0b514e180dbdJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-055f-9000000000-7e23cd40dde01cb89b6fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-9000000000-b70087d61cbf63d60bd5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-08a8f57a90b00db3596aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-052f-9000000000-69148177e3417cc669fdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-052f-9000000000-7ebca2648ffd63942337JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-055f-9000000000-7e23cd40dde01cb89b6fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9000000000-53a465f38bad658bb673JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-9145b21c5f3ae37774e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-686e7cdc50d3fda3a0ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-9000000000-53a465f38bad658bb673JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-9145b21c5f3ae37774e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-686e7cdc50d3fda3a0ffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-61d09b30d6a547d109fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4d4d1c2159c658c4ee24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-2119b542a1efb8432d12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-61d09b30d6a547d109fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-4d4d1c2159c658c4ee24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-2119b542a1efb8432d12JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-4256cf8850659dacd159JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-cb6c5eeb586ac4d5655eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-21e6cc4261bed22ecbf8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-a749e449b2f26d0e75a2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-b0818591ffca1f29c3ecJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-d2c85c870494f5dbfc6bJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-054o-9000000000-061591a78bc1cdeda799JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Antonelli, A., Castellari, L., Zambonelli, C., Carnacini, A. (1999). "Yeast influence on volatile composition of wines." J Agric Food Chem 47:1139-1144.10552428
  • Tsakiris, A., Koutinas, A. A., Psarianos, C., Kourkoutas, Y., Bekatorou, A. (2010). "A new process for wine production by penetration of yeast in uncrushed frozen grapes." Appl Biochem Biotechnol 162:1109-1121.20151225
  • Patel, S., Shibamoto, T. (2002). "Effect of different strains of Saccharomyces cerevisiae on production of volatiles in Napa Gamay wine and Petite Sirah wine." J Agric Food Chem 50:5649-5653.12236692
Synthesis Reference:Tsuchida, Takashi; Sakuma, Shuji. Ethanol to 1-butanol on hydroxyapatite. Shokubai (2007), 49(3), 238-243.
External Links:
ResourceLink
CHEBI ID28885
HMDB IDHMDB04327
Pubchem Compound ID263
Kegg IDC06142
ChemSpider ID258
FOODB IDFDB031032
Wikipedia1-Butanol
BioCyc IDBUTANOL