Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:07:56 UTC |
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Update date | 2020-09-17 15:35:19 UTC |
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Primary ID | FDB008131 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Isopentyl alcohol |
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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). |
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CAS Number | 123-51-3 |
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Structure | |
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Synonyms | Synonym | Source |
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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 | 1-Butanol, 3-methyl- | biospider | 1-Hydroxy-3-methylbutane | biospider | 3-METHYL-1-BUTANOL, REAG | biospider | 3-methyl-Butanol | biospider | 3-methylbutanoI | biospider | 3-Metil-butanolo | biospider | 6423-06-9 (magnesium salt) | biospider | Alcool amilico | biospider | Amylowy alkohol | biospider | Butanol, 3-methyl- | biospider | FEMA 2057 | db_source | Fuseloel | biospider | Fuseloel (german) | biospider | Iso-amyl alcohol | biospider | Iso-amylalkohol(german) | biospider | Isoamyl alcohol (primary and secondary) | biospider | Isoamyl alcohol, acs | biospider | Isoamyl alcohol, primary | biospider | Isopentyl alcohol (8CI) | biospider | Isopentyl alcohol, 8CI | db_source | Magnesium bis(3-methylbutan-1-olate) | biospider |
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Predicted Properties | |
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Chemical Formula | C5H12O |
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IUPAC name | 3-methylbutan-1-ol |
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InChI Identifier | InChI=1S/C5H12O/c1-5(2)3-4-6/h5-6H,3-4H2,1-2H3 |
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InChI Key | PHTQWCKDNZKARW-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)CCO |
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Average Molecular Weight | 88.1482 |
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Monoisotopic Molecular Weight | 88.088815006 |
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Classification |
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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). |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Alcohols and polyols |
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Direct Parent | Primary alcohols |
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Alternative Parents | |
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Substituents | - Hydrocarbon derivative
- Primary alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 68.13%; H 13.72%; O 18.15% | DFC |
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Melting Point | Mp -117.2° | DFC |
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Boiling Point | Bp 132° | DFC |
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Experimental Water Solubility | 26.7 mg/mL at 25 oC | RIDDICK,JA et al. (1986) |
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Experimental logP | 1.16 | HANSCH,C ET AL. (1995) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | d154 0.81 | DFC |
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Refractive Index | n20D 1.4055 | DFC |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-052f-9000000000-370bf1c231476fa54243 | 2015-03-01 | View Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71 | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-8f690089412de62c1345 | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-7c2ce9899425d009c30d | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-bf852ef18965656b4e96 | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-0a4l-9000000000-e1eb02399a8e4a0e1d71 | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-8f690089412de62c1345 | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-7c2ce9899425d009c30d | Spectrum | GC-MS | Isopentyl alcohol, non-derivatized, GC-MS Spectrum | splash10-052f-9000000000-bf852ef18965656b4e96 | Spectrum | Predicted GC-MS | Isopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-9000000000-21a2665671fd17ea55ce | Spectrum | Predicted GC-MS | Isopentyl alcohol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fdp-9400000000-2a46653460ba2c8da268 | Spectrum | Predicted GC-MS | Isopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isopentyl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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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 |
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NMR | Type | Description | | View |
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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 |
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External Links |
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ChemSpider ID | 29000 |
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ChEMBL ID | CHEMBL372396 |
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KEGG Compound ID | C07328 |
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Pubchem Compound ID | 31260 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15837 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB02296 |
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HMDB ID | HMDB06007 |
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CRC / DFC (Dictionary of Food Compounds) ID | DCL40-H:DCL40-H |
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EAFUS ID | 1825 |
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Dr. Duke ID | 3-METHYL-BUTANOL|ISOAMYL-ALCOHOL|3-METHYL-BUTAN-1-OL|3-METHYL-1-BUTANOL |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | IP3 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 123-51-3 |
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GoodScent ID | rw1014671 |
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SuperScent ID | 31260 |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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whiskey |
- 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
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| malt |
- 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 |
- 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 |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| oil |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| alcoholic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fruity |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| banana |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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