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2-Butanol (FDB003382)

Record Information
Version1.0
Creation date2010-04-08 22:05:47 UTC
Update date2019-11-26 02:59:07 UTC
Primary IDFDB003382
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-Butanol
DescriptionIsolated from fruit of blackcurrant (Ribes nigrum) and other fruitsand is also present in various cheeses, wines, black tea, endive and clary sage. Flavouring agent 2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. This secondary alcohol is a flammable, colorless liquid that is soluble in 12 parts water and completely miscible with polar organic solvents such as ethers and other alcohols. It is produced on a large scale, primarily as a precursor to the industrial solvent methyl ethyl ketone. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(-)-2-butanol and (S)-(+)-2-butanol. It is normally found as an equal mixture of the two stereoisomers — a racemic mixture. 2-Butanol is found in many foods, some of which are highbush blueberry, milk and milk products, rosemary, and tea.
CAS Number78-92-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted 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
Chemical FormulaC4H10O
IUPAC namebutan-2-ol
InChI IdentifierInChI=1S/C4H10O/c1-3-4(2)5/h4-5H,3H2,1-2H3
InChI KeyBTANRVKWQNVYAZ-UHFFFAOYSA-N
Isomeric SMILESCCC(C)O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
Classification
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

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 64.82%; H 13.60%; O 21.59%DFC
Melting Point-114.7 oC
Boiling PointNot Available
Experimental Water Solubility181 mg/mL at 25 oCHEFTER,GT (1984A)
Experimental logP0.61HANSCH,C ET AL. (1995)
Experimental pKa17.6
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0002-9000000000-771b68c9e84f9101ec6d2015-03-01View Spectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-69a1867b969261fbdf06Spectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ccad0f1d1aa3a22b166dSpectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ef7cd62aa636fe20c0ebSpectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-69a1867b969261fbdf06Spectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ccad0f1d1aa3a22b166dSpectrum
GC-MS2-Butanol, non-derivatized, GC-MS Spectrumsplash10-0002-9000000000-ef7cd62aa636fe20c0ebSpectrum
Predicted GC-MS2-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056r-9000000000-88d60fe7c83e55440455Spectrum
Predicted GC-MS2-Butanol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00wi-9300000000-cb203a619c04be21a120Spectrum
Predicted GC-MS2-Butanol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-de5df4899287d1e83d602015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-9000000000-920e6cee03b9b4c5fb072015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-fab3878f8110affe65c22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9000000000-4256cf8850659dacd1592021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9000000000-196f07d2f495373b81ea2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-2e44988393496e99b51f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-4e78283c55f36c9feda22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-c325f8fdffc2a59e1d102015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-18f52ab5703ab9a7a1b02015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9000000000-2aeeb231544bed908c5f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-9d972b42b1bf6cc3b0d82021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-0a72cbd1fb3863ce68eb2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID6320
ChEMBL IDCHEMBL45462
KEGG Compound IDC17690
Pubchem Compound ID6568
Pubchem Substance IDNot Available
ChEBI ID35687
Phenol-Explorer IDNot Available
DrugBank IDDB02606
HMDB IDHMDB11469
CRC / DFC (Dictionary of Food Compounds) IDCXC58-F:CXC58-F
EAFUS ID381
Dr. Duke IDSEC-BUTANOL|BUTAN-2-OL|2-BUTANOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID78-92-2
GoodScent IDrw1012951
SuperScent ID6568
Wikipedia ID2-butanol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
oily
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
apricot
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).