Cannabis Compound Database: Showing Compound Card for lsoamyl alcohol (CDB000622)

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Record Information

Version

1.0

Created at

2020-03-19 00:47:09 UTC

Updated at

2020-12-07 19:07:35 UTC

CannabisDB ID

CDB000622

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

lsoamyl alcohol

Description

Isoamyl 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-HYDROXY-3-methylbutane	ChEBI
2-Methyl-4-butanol	ChEBI
3-Methyl-1-butanol	ChEBI
3-Methylbutanol	ChEBI
Alcool isoamylique	ChEBI
I-amyl alcohol	ChEBI
Iso-amylalkohol	ChEBI
Isoamyl alcohol	ChEBI
Isobutylcarbinol	ChEBI
Isopentan-1-ol	ChEBI
Isopentyl alcohol	ChEBI
Isopentylalkohol	ChEBI
Primary isoamyl alcohol	ChEBI
Isopentyl alcohol, 1-(14)C-labeled	MeSH
Isopentyl alcohol, barium salt	MeSH
Isopentyl alcohol, lead (2+) salt	MeSH
Isopentyl alcohol, magnesium salt	MeSH
Isopentyl alcohol, potassium salt	MeSH
Isopentyl alcohol, sodium salt	MeSH
Isopentyl alcohol, strontium salt	MeSH
3-Methyl-butan-(1)-ol	HMDB
3-Methyl-butanol	HMDB
3-Methylbutan-1-ol	HMDB
3-MethylbutanoI	HMDB
Butan-1-ol, 3-methyl	HMDB
Fermentation amyl alcohol	HMDB
Fusel oil	HMDB
iso-Amyl alcohol	HMDB
Isoamyl alcohol (3-methyl butanol)	HMDB
Isoamyl alcohol (natural)	HMDB
Isoamyl alkohol	HMDB
Isoamylalcohol	HMDB
Isoamylol	HMDB
Isobutyl carbinol	HMDB
Methyl-3-butan-1-ol	HMDB
Isopentanol	ChEBI

Chemical Formula

C₅H₁₂O

Average Molecular Weight

88.15

Monoisotopic Molecular Weight

88.0888

IUPAC Name

3-methylbutan-1-ol

Traditional Name

isoamyl alcohol

CAS Registry Number

123-51-3

SMILES

CC(C)CCO

InChI Identifier

InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3

InChI Key

PHTQWCKDNZKARW-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).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Primary alcohols

Alternative Parents

Hydrocarbon derivatives

Substituents

Hydrocarbon derivative
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:15837 )
alkyl alcohol (CHEBI:15837 )
Fatty alcohols (LMFA05000108 )
a small molecule (CPD-7032 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Microbe:

Escherichia:

Escherichia coli

Plant:

Role

Industrial application:

Food and nutrition:

Flavoring agent

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-117.2 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	26.7 mg/mL at 25 °C	Not Available
logP	1.16	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	1.33	ALOGPS
logP	1.09	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Acidic)	17.17	ChemAxon
pKa (Strongest Basic)	-1.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.68 m³·mol⁻¹	ChemAxon
Polarizability	11.03 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-052f-9000000000-370bf1c231476fa54243	2015-03-01	View Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-8f690089412de62c1345	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-7c2ce9899425d009c30d	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-bf852ef18965656b4e96	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-8f690089412de62c1345	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-7c2ce9899425d009c30d	Spectrum
GC-MS	lsoamyl alcohol, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-bf852ef18965656b4e96	Spectrum
Predicted GC-MS	lsoamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-21a2665671fd17ea55ce	Spectrum
Predicted GC-MS	lsoamyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fdp-9400000000-2a46653460ba2c8da268	Spectrum
Predicted GC-MS	lsoamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	lsoamyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0006-9000000000-2c1d0ae92e43acc092e6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0006-9000000000-8dd3d034bf479e8803ba	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0006-9000000000-3c9aeb8ba4420ca8a165	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0006-9000000000-9e3cac2c0ecb4470e212	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-0006-9000000000-fe95a0016d6b985d7e2c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0006-9000000000-46c43a114223f5a591b7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0006-9000000000-e5423b2ff284e82d6dd1	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0006-9000000000-f6e908787eb43732d644	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 6V, positive	splash10-0006-9000000000-ff2d0161e440ffcb6223	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 8V, positive	splash10-0006-9000000000-9deabd7a6d74f80abdda	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 12V, positive	splash10-0006-9000000000-fac465f943fed2ef3090	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 16V, positive	splash10-0006-9000000000-9cbb4df3621ddb73950e	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-9000000000-7bbd6dbb0b9915076ca1	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-c74cb455e67c059f399c	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-f827e13ae4abb1b14fbb	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dr-9000000000-7bbd6dbb0b9915076ca1	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9000000000-c74cb455e67c059f399c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9000000000-f827e13ae4abb1b14fbb	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-7264596be9d872886688	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9000000000-cc98e6ceeea595509f4c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9000000000-c1813a13047771c3400a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-7264596be9d872886688	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-9000000000-cc98e6ceeea595509f4c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9000000000-c1813a13047771c3400a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9000000000-fdb2b51ca693bf9b93b2	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0006007

DrugBank ID

DB02296

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isoamyl alcohol

METLIN ID

Not Available

PubChem Compound

31260

PDB ID

IP3

ChEBI ID

15837

References

General References

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 ]
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 ]
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 ]

Showing Compound Card for lsoamyl alcohol (CDB000622)

Structure for CDB000622 (lsoamyl alcohol)