Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2015-07-20 22:18:55 UTC
Primary IDFDB008131
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIsopentyl alcohol
DescriptionMajor component of fusel oil. A common constit. of plant oils, free and as esters. Present in many wines and spirits. Flavouring agent Isopentanol or Isoamyl alcohol is one of several isomers of amyl alcohol. It is a by-product of gut microbial fermentation (PMID: 17452087). It can be produced by 3-methylbutanal reductase (EC 1.1.1.265) from 3 methylbutanal. Isoamyl alcohol is the major higher chain alcohol in alcoholic beverages and is present in cider, mead, beer, wine, and spirits to varying degrees, being obtained by the fermentation of starches. Isopentanol has been shown to induce expression of CYP3A and CYP2E1 in human liver (PMID: 7574728)
CAS Number123-51-3
Structure
Thumb
Synonyms
SynonymSource
1-Butanol, 3-methyl-biospider
1-Hydroxy-3-methylbutanebiospider
2-Methyl-4-butanolbiospider
3-Methyl-1-butanolChEBI
3-METHYL-1-BUTANOL, REAGbiospider
3-Methyl-butan-(1)-olbiospider
3-methyl-Butanolbiospider
3-Methylbutan-1-olbiospider
3-methylbutanoIbiospider
3-Methylbutanolbiospider
3-Metil-butanolobiospider
6423-06-9 (magnesium salt)biospider
Alcool amilicobiospider
Alcool isoamyliquebiospider
Amylowy alkoholbiospider
Butan-1-ol, 3-methylbiospider
Butanol, 3-methyl-biospider
FEMA 2057db_source
Fermentation amyl alcoholbiospider
Fusel oilbiospider
Fuseloelbiospider
Fuseloel (german)biospider
I-amyl alcoholbiospider
Iso-amyl alcoholbiospider
Iso-amylalkoholbiospider
Iso-amylalkohol(german)biospider
Isoamyl alcoholdb_source
Isoamyl alcohol (3-methyl butanol)biospider
Isoamyl alcohol (natural)HMDB
Isoamyl alcohol (primary and secondary)biospider
Isoamyl alcohol, acsbiospider
Isoamyl alcohol, primarybiospider
Isoamyl alkoholbiospider
Isoamylalcoholbiospider
Isoamylolbiospider
Isobutyl carbinolbiospider
Isobutylcarbinolbiospider
Isopentan-1-olbiospider
Isopentanolbiospider
Isopentyl alcoholbiospider
Isopentyl alcohol (8CI)biospider
Isopentyl alcohol, 8CIdb_source
Isopentylalkoholbiospider
Magnesium bis(3-methylbutan-1-olate)biospider
Methyl-3-butan-1-olbiospider
Primary isoamyl alcoholbiospider
Predicted Properties
PropertyValueSource
Water Solubility38 g/LALOGPS
logP1.33ALOGPS
logP1.09ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)17.17ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.68 m³·mol⁻¹ChemAxon
Polarizability11.03 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H12O
IUPAC name3-methylbutan-1-ol
InChI IdentifierInChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
InChI KeyInChIKey=PHTQWCKDNZKARW-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCO
Average Molecular Weight88
Monoisotopic Molecular Weight88
Classification
DescriptionThis compound belongs to the class of organic compounds known as primary alcohols. These 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 68.13%; H 13.72%; O 18.15%DFC
Melting PointMp -117.2°DFC
Boiling PointBp 132°DFC
Experimental Water Solubility26.7 mg/mL at 25 oCRIDDICK,JA et al. (1986)
Experimental logP1.16HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
Densityd154 0.81DFC
Refractive Indexn20D 1.4055DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-8f690089412de62c1345View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-7c2ce9899425d009c30dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-bf852ef18965656b4e96View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-21a2665671fd17ea55ceView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdp-9400000000-2a46653460ba2c8da268View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aView in MoNA
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-370bf1c231476fa54243View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID29000
ChEMBL IDCHEMBL372396
KEGG Compound IDC07328
Pubchem Compound ID31260
Pubchem Substance IDNot Available
ChEBI ID15837
Phenol-Explorer IDNot Available
DrugBank IDDB02296
HMDB IDHMDB06007
CRC / DFC (Dictionary of Food Compounds) IDDCL40-H:DCL40-H
EAFUS ID1825
Dr. Duke ID3-METHYL-BUTANOL|ISOAMYL-ALCOHOL|3-METHYL-BUTAN-1-OL|3-METHYL-1-BUTANOL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDIP3
Flavornet ID123-51-3
GoodScent IDrw1014671
SuperScent ID31260
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
emeticDUKE
irritantDUKE
perfume48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
whiskey
  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
  2. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
  3. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
malt
  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
burnt
  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
fusel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
oil
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
alcoholic
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
banana
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
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).