Showing Compound Card for lsoamyl alcohol (CDB000622)

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Record Information
Version1.0
Created at2020-03-19 00:47:09 UTC
Updated at2020-12-07 19:07:35 UTC
CannabisDB IDCDB000622
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namelsoamyl 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 ). Isoamyl alcohol has been detected as a volatile component in cannabis plant samples (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
Isopentyl alcohol, 1-(14)C-labeledMeSH
Isopentyl alcohol, barium saltMeSH
Isopentyl alcohol, lead (2+) saltMeSH
Isopentyl alcohol, magnesium saltMeSH
Isopentyl alcohol, potassium saltMeSH
Isopentyl alcohol, sodium saltMeSH
Isopentyl alcohol, strontium saltMeSH
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
IsopentanolChEBI
Chemical FormulaC5H12O
Average Molecular Weight88.15
Monoisotopic Molecular Weight88.0888
IUPAC Name3-methylbutan-1-ol
Traditional Nameisoamyl alcohol
CAS Registry Number123-51-3
SMILES
CC(C)CCO
InChI Identifier
InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3
InChI KeyPHTQWCKDNZKARW-UHFFFAOYSA-N
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
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point-117.2 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.7 mg/mL at 25 °CNot Available
logP1.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052f-9000000000-370bf1c231476fa542432015-03-01View Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-e1eb02399a8e4a0e1d71Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8f690089412de62c1345Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7c2ce9899425d009c30dSpectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-bf852ef18965656b4e96Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-e1eb02399a8e4a0e1d71Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-8f690089412de62c1345Spectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-7c2ce9899425d009c30dSpectrum
GC-MSlsoamyl alcohol, non-derivatized, GC-MS Spectrumsplash10-052f-9000000000-bf852ef18965656b4e96Spectrum
Predicted GC-MSlsoamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9000000000-21a2665671fd17ea55ceSpectrum
Predicted GC-MSlsoamyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdp-9400000000-2a46653460ba2c8da268Spectrum
Predicted GC-MSlsoamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSlsoamyl 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
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0006007
DrugBank IDDB02296
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008131
KNApSAcK IDC00050468
Chemspider ID29000
KEGG Compound IDC07328
BioCyc IDCPD-7032
BiGG IDNot Available
Wikipedia LinkIsoamyl alcohol
METLIN IDNot Available
PubChem Compound31260
PDB IDIP3
ChEBI ID15837
References
General References
  1. Boumba VA, Ziavrou KS, Vougiouklakis T: Biochemical pathways generating post-mortem volatile compounds co-detected during forensic ethanol analyses. Forensic Sci Int. 2008 Jan 30;174(2-3):133-51. doi: 10.1016/j.forsciint.2007.03.018. Epub 2007 Apr 23. [PubMed:17452087 ]
  2. Kostrubsky VE, Strom SC, Wood SG, Wrighton SA, Sinclair PR, Sinclair JF: Ethanol and isopentanol increase CYP3A and CYP2E in primary cultures of human hepatocytes. Arch Biochem Biophys. 1995 Oct 1;322(2):516-20. doi: 10.1006/abbi.1995.1495. [PubMed:7574728 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]