Record Information
Version1.0
Creation date2010-04-08 22:07:56 UTC
Update date2020-09-17 15:35:19 UTC
Primary IDFDB008131
Secondary Accession Numbers
  • FDB030444
Chemical Information
FooDB NameIsopentyl alcohol
DescriptionIsoamyl alcohol or Isopentanol, also known as isopentyl alcohol or iso-amylalkohol, belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the alcohol functional group, attached to a primary carbon, with the general structure RCOH (R=alkyl, aryl). Isoamyl alcohol is a very hydrophobic molecule, practically insoluble in water but readily soluble in organic solvents such as methanol, ethanol and ethyl acetate. Thus, isopentanol is considered to be a fatty alcohol lipidic molecule. Isopentyl alcohol is one of several isomers of amyl alcohol. It is a by-product of gut microbial fermentation (PMID: 17452087). Isopentanol is an alcoholic, banana, and burnt tasting compound. Due to its flavour and aroma, it is an ingredient in the production of banana oil, an ester found in nature and also produced as a flavouring in industry. Isoamyl alcohol can be produced by 3-methylbutanal reductase (EC 1.1.1.265) from 3-methylbutanal. In alcoholic beverages, isopentyl alcohol is also the major higher chain alcohol and it is present in cider, mead, beer, wine, and spirits to varying degrees, being a product of 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-HYDROXY-3-methylbutaneChEBI
2-Methyl-4-butanolChEBI
3-Methyl-1-butanolChEBI
3-MethylbutanolChEBI
Alcool isoamyliqueChEBI
I-amyl alcoholChEBI
Iso-amylalkoholChEBI
Isoamyl alcoholChEBI
IsobutylcarbinolChEBI
Isopentan-1-olChEBI
Isopentyl alcoholChEBI
IsopentylalkoholChEBI
Primary isoamyl alcoholChEBI
3-Methyl-butan-(1)-olHMDB
3-Methyl-butanolHMDB
3-Methylbutan-1-olHMDB
3-MethylbutanoIHMDB
Butan-1-ol, 3-methylHMDB
Fermentation amyl alcoholHMDB
Fusel oilHMDB
Iso-amyl alcoholHMDB
Isoamyl alcohol (3-methyl butanol)HMDB
Isoamyl alcohol (natural)HMDB
Isoamyl alkoholHMDB
IsoamylalcoholHMDB
IsoamylolHMDB
Isobutyl carbinolHMDB
Methyl-3-butan-1-olHMDB
Isopentyl alcohol, barium saltHMDB
Isopentyl alcohol, magnesium saltHMDB
Isopentyl alcohol, sodium saltHMDB
Isopentyl alcohol, lead (2+) saltHMDB
Isopentyl alcohol, potassium saltHMDB
Isopentyl alcohol, strontium saltHMDB
Isopentyl alcohol, 1-(14)C-labeledHMDB
IsopentanolChEBI
1-Butanol, 3-methyl-biospider
1-Hydroxy-3-methylbutanebiospider
3-METHYL-1-BUTANOL, REAGbiospider
3-methyl-Butanolbiospider
3-methylbutanoIbiospider
3-Metil-butanolobiospider
6423-06-9 (magnesium salt)biospider
Alcool amilicobiospider
Amylowy alkoholbiospider
Butanol, 3-methyl-biospider
FEMA 2057db_source
Fuseloelbiospider
Fuseloel (german)biospider
Iso-amylalkohol(german)biospider
Isoamyl alcohol (primary and secondary)biospider
Isoamyl alcohol, acsbiospider
Isoamyl alcohol, primarybiospider
Isopentyl alcohol (8CI)biospider
Isopentyl alcohol, 8CIdb_source
Magnesium bis(3-methylbutan-1-olate)biospider
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
BioavailabilityYesChemAxon
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 KeyPHTQWCKDNZKARW-UHFFFAOYSA-N
Isomeric SMILESCC(C)CCO
Average Molecular Weight88.1482
Monoisotopic Molecular Weight88.088815006
Classification
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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 KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-8f690089412de62c1345JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-7c2ce9899425d009c30dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-bf852ef18965656b4e96JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-8f690089412de62c1345JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-7c2ce9899425d009c30dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-052f-9000000000-bf852ef18965656b4e96JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-21a2665671fd17ea55ceJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fdp-9400000000-2a46653460ba2c8da268JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0006-9000000000-2c1d0ae92e43acc092e6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0006-9000000000-8dd3d034bf479e8803baJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0006-9000000000-3c9aeb8ba4420ca8a165JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0006-9000000000-9e3cac2c0ecb4470e212JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0006-9000000000-fe95a0016d6b985d7e2cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0006-9000000000-46c43a114223f5a591b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0006-9000000000-e5423b2ff284e82d6dd1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-9000000000-f6e908787eb43732d644JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-0006-9000000000-ff2d0161e440ffcb6223JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-0006-9000000000-9deabd7a6d74f80abddaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-0006-9000000000-fac465f943fed2ef3090JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-0006-9000000000-9cbb4df3621ddb73950eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d872886688JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400aJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-370bf1c231476fa54243JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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
Food Biomarker OntologyNot Available
VMH IDNot Available
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).