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Isopentyl alcohol (FDB008131)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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 FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-370bf1c231476fa542432015-03-01View Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-e1eb02399a8e4a0e1d71Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8f690089412de62c1345Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7c2ce9899425d009c30dSpectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-bf852ef18965656b4e96Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-e1eb02399a8e4a0e1d71Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8f690089412de62c1345Spectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7c2ce9899425d009c30dSpectrum
GC-MSIsopentyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-bf852ef18965656b4e96Spectrum
Predicted GC-MSIsopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-21a2665671fd17ea55ceSpectrum
Predicted GC-MSIsopentyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdp-9400000000-2a46653460ba2c8da268Spectrum
Predicted GC-MSIsopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSIsopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-0006-9000000000-2c1d0ae92e43acc092e62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-0006-9000000000-8dd3d034bf479e8803ba2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0006-9000000000-3c9aeb8ba4420ca8a1652020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0006-9000000000-9e3cac2c0ecb4470e2122020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-0006-9000000000-fe95a0016d6b985d7e2c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0006-9000000000-46c43a114223f5a591b72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0006-9000000000-e5423b2ff284e82d6dd12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-0006-9000000000-f6e908787eb43732d6442020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 6V, positivesplash10-0006-9000000000-ff2d0161e440ffcb62232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 8V, positivesplash10-0006-9000000000-9deabd7a6d74f80abdda2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 12V, positivesplash10-0006-9000000000-fac465f943fed2ef30902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 16V, positivesplash10-0006-9000000000-9cbb4df3621ddb73950e2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca12015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399c2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbb2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-9000000000-7bbd6dbb0b9915076ca12015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000000000-c74cb455e67c059f399c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9000000000-f827e13ae4abb1b14fbb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d8728866882015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-7264596be9d8728866882015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9000000000-cc98e6ceeea595509f4c2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9000000000-c1813a13047771c3400a2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-9000000000-fdb2b51ca693bf9b93b22021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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).