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| Record Information |
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| Version | 4.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2009-07-25 00:12:04 UTC |
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| Update Date | 2019-07-23 05:58:29 UTC |
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| HMDB ID | HMDB0013036 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 1-Pentanol |
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| Description | 1-Pentanol, also known as butylcarbinol or 1-pentyl alcohol, 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). Thus, 1-pentanol is considered to be a fatty alcohol lipid molecule. 1-Pentanol is an organic compound with the formula C5H12O. 1-Pentanol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. All eight isomers of 1-Pentanol are known:; It is a colourless liquid of density 0.8247 g/cm3 (0 oC), boiling at 131.6 oC, slightly soluble in water, easily soluble in organic solvents. 1-Pentanol exists in all eukaryotes, ranging from yeast to humans. 1-Pentanol is a sweet, balsamic, and fusel tasting compound. Outside of the human body, 1-Pentanol is found, on average, in the highest concentration within a few different foods, such as black walnuts, common thymes, and tea and in a lower concentration in safflowers, highbush blueberries, and kohlrabis. 1-Pentanol has also been detected, but not quantified in, several different foods, such as corns, garden tomato (var.), allspices, cherry tomato, and evergreen blackberries. This could make 1-pentanol a potential biomarker for the consumption of these foods. It possesses a characteristic strong smell and a sharp burning taste. The other amyl alcohols may be obtained synthetically. It is a solid that melts at 48 to 50 oC and boils at 112.3 oC. On passing its vapour through a red-hot tube, it decomposes with production of acetylene, ethylene, propylene, and other compounds. Of these, tertiary 1-Pentanol has been the most difficult to obtain, its synthesis having first been reported in 1891, by L. Tissier (Comptes Rendus, 1891, 112, p. 1065) by the reduction of a mixture of trimethyl acetic acid and trimethylacetyl chloride with sodium amalgam. It is oxidized by chromic acid to isovaleraldehyde, and it forms crystalline addition compounds with calcium chloride and tin(IV) chloride. When pure, it is nontoxic, while the impure product is toxic. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-Pentol | ChEBI | | 1-Pentyl alcohol | ChEBI | | Alcool amylique | ChEBI | | Amyl alcohol, normal | ChEBI | | Amylalkohol | ChEBI | | Amylol | ChEBI | | Butylcarbinol | ChEBI | | N-Amyl alcohol | ChEBI | | N-Amylalkohol | ChEBI | | N-Butylcarbinol | ChEBI | | N-C5H11OH | ChEBI | | N-Pentan-1-ol | ChEBI | | N-Pentyl alcohol | ChEBI | | Pentanol-1 | ChEBI | | Pentyl alcohol | ChEBI | | Pentylalkohol | ChEBI | | Primary amyl alcohol | ChEBI | | Amyl alcohol | HMDB | | Amyl alcohol (natural) | HMDB | | Amyl alcohol normal | HMDB | | Butyl carbinol | HMDB | | C5 Alcohol | HMDB | | N-Pentanol | HMDB | | N-Pentyl-alcohol | HMDB | | Pentan-1-ol | HMDB | | Pentanol | HMDB | | Pentanols | HMDB | | Pentasol | HMDB | | Pentyl-alcohol | HMDB | | Petan-1-ol | HMDB | | Primary-N-amyl alcohol | HMDB | | N-Pentanol, 1-(13)C-labeled CPD | HMDB | | N-Pentanol, barium salt | HMDB | | N-Pentanol, magnesium salt | HMDB | | N-Pentanol, titanium (4+) salt | HMDB | | N-Pentanol, aluminum salt | HMDB | | N-Pentanol, calcium salt | HMDB | | N-Pentanol, potassium salt | HMDB | | N-Pentanol, sodium salt | HMDB | | 1-Pentanol | ChEBI |
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| Chemical Formula | C5H12O |
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| Average Molecular Weight | 88.1482 |
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| Monoisotopic Molecular Weight | 88.088815006 |
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| IUPAC Name | pentan-1-ol |
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| Traditional Name | amyl alcohol |
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| CAS Registry Number | 71-41-0 |
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| SMILES | CCCCCO |
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| InChI Identifier | InChI=1S/C5H12O/c1-2-3-4-5-6/h6H,2-5H2,1H3 |
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| InChI Key | AMQJEAYHLZJPGS-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | -78.9 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 22 mg/mL at 25 °C | Not Available | | LogP | 1.51 | SANGSTER (1994) |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-5244661275aa6b95b9a0 | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-a8f61d2d09e6d85a0da6 | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-26fa66c5f2883093c25e | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-86ba80dfb4a247abdead | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-5244661275aa6b95b9a0 | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-a8f61d2d09e6d85a0da6 | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-052f-9000000000-26fa66c5f2883093c25e | Spectrum | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0006-9000000000-86ba80dfb4a247abdead | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a6u-9000000000-e8d9380a14b5b0b3b4a9 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9200000000-4c1b7248f90571b974e4 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00dr-9000000000-d22868bc6f5389bbac24 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9000000000-89f22f7ad4cabb8583c7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0596-9000000000-9e10eda056754554eb68 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-8843f2a5c4b4e08e336b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-96da06aaf672d71e1afa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05mo-9000000000-cd983bb43429b412ca51 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-052f-9000000000-c25069a0af8dacf4d39d | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Biological Properties |
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| Cellular Locations | Not Available |
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| Biospecimen Locations | |
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| Tissue Locations | Not Available |
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| Pathways | |
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| Normal Concentrations |
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| Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Children (1-13 years old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Newborn (0-30 days old) | Both | Normal | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Clostridium difficile infection | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative Colitis | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) non progressor | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details | | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | | Feces | Detected but not Quantified | | Children (1-13 years old) | Both | Autism | | details | | Feces | Detected but not Quantified | | Children (1-13 years old) | Both | Pervasive Developmental Disorder Not Otherwise Specified | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Ulcerative colitis |
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- Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
| | Nonalcoholic fatty liver disease |
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- Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
| | Autism |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| | Pervasive developmental disorder not otherwise specified |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FoodDB ID | FDB008230 |
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| KNApSAcK ID | C00035784 |
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| Chemspider ID | 6040 |
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| KEGG Compound ID | C16834 |
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| BioCyc ID | PENTANOL |
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| BiGG ID | Not Available |
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| Wikipedia Link | 1-Pentanol |
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| METLIN ID | Not Available |
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| PubChem Compound | 6276 |
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| PDB ID | PE9 |
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| ChEBI ID | 44884 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Download (PDF) |
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| General References | Not Available |
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