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Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-13 02:57:08 UTC |
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Update Date | 2021-10-13 04:42:14 UTC |
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HMDB ID | HMDB0003671 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Heptanone |
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Description | 2-Heptanone, also known as butylacetone or heptan-2-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone is a ketone with the molecular formula C7H14O. 2-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone is a sweet, cinnamon, and coconut tasting compound. 2-Heptanone is found, on average, in the highest concentration within a few different foods, such as corns, cow milk, and peppermints. 2-Heptanone has also been detected, but not quantified in several different foods, such as tarragons, blackberries, tortilla chips, ceylon cinnamons, and evergreen blackberries. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. 2-Heptanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, crohn's disease, and hepatic encephalopathy; 2-heptanone has also been linked to the inborn metabolic disorder celiac disease. It is a colorless to white liquid with a banana-like, fruity odor. |
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Structure | InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 |
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Synonyms | Value | Source |
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Butylacetone | ChEBI | Methyl N-amyl ketone | ChEBI | Methyl pentyl ketone | ChEBI | N-Amyl methyl ketone | ChEBI | N-Pentyl methyl ketone | ChEBI | Heptan-2-one | Kegg | Methyl-N-amyl ketone | MeSH | 1-Methylhexanal | HMDB | 2-Oxoheptane | HMDB | Amyl methyl ketone | HMDB | Methyl amyl ketone | HMDB | Methyl N-pentyl ketone | HMDB | Pentyl methyl ketone | HMDB | 2-Heptanone | ChEBI |
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Chemical Formula | C7H14O |
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Average Molecular Weight | 114.1855 |
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Monoisotopic Molecular Weight | 114.10446507 |
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IUPAC Name | heptan-2-one |
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Traditional Name | 2-heptanone |
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CAS Registry Number | 110-43-0 |
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SMILES | CCCCCC(C)=O |
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InChI Identifier | InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3 |
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InChI Key | CATSNJVOTSVZJV-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. |
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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 | Carbonyl compounds |
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Direct Parent | Ketones |
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Alternative Parents | |
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Substituents | - Ketone
- Organic oxide
- Hydrocarbon derivative
- 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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Physiological effect | |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Liquid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | -35 °C | Not Available | Boiling Point | 149.00 to 150.00 °C. @ 760.00 mm Hg | The Good Scents Company Information System | Water Solubility | 4.3 mg/mL at 25 °C | Not Available | LogP | 1.98 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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2-Heptanone,1TMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C | 1091.2 | Semi standard non polar | 33892256 | 2-Heptanone,1TMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C | 1053.7 | Standard non polar | 33892256 | 2-Heptanone,1TMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C | 1102.1 | Standard polar | 33892256 | 2-Heptanone,1TMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C | 1049.5 | Semi standard non polar | 33892256 | 2-Heptanone,1TMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C | 1050.7 | Standard non polar | 33892256 | 2-Heptanone,1TMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C | 1111.6 | Standard polar | 33892256 | 2-Heptanone,1TBDMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C(C)(C)C | 1305.6 | Semi standard non polar | 33892256 | 2-Heptanone,1TBDMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C(C)(C)C | 1254.4 | Standard non polar | 33892256 | 2-Heptanone,1TBDMS,isomer #1 | CCCCC=C(C)O[Si](C)(C)C(C)(C)C | 1296.3 | Standard polar | 33892256 | 2-Heptanone,1TBDMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C(C)(C)C | 1260.0 | Semi standard non polar | 33892256 | 2-Heptanone,1TBDMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C(C)(C)C | 1244.6 | Standard non polar | 33892256 | 2-Heptanone,1TBDMS,isomer #2 | C=C(CCCCC)O[Si](C)(C)C(C)(C)C | 1310.7 | Standard polar | 33892256 |
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Spectra |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | - Cerebrospinal Fluid (CSF)
- Feces
- Saliva
- Urine
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 0 - 0.18 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Both | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 2072.651-22215.313 nmol/g wet feces | Children (1-13 years old) | Not Specified | Normal | | details | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.7 uM | Adult (>18 years old) | Both | Hepatic encephalopathy | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Campylobacter jejuni infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Clostridium difficile infection | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative Colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Feces | Detected and Quantified | 0-479132.639 nmol/g wet feces | Children (1-13 years old) | Not Specified | Treated celiac disease | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Breast cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Hepatic encephalopathy |
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- Goldberg EM, Blendis LM, Sandler S: A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. J Chromatogr. 1981 Dec 11;226(2):291-9. [PubMed:7320160 ]
| 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 ]
- Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
| 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 ]
| Celiac disease |
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- Di Cagno R, De Angelis M, De Pasquale I, Ndagijimana M, Vernocchi P, Ricciuti P, Gagliardi F, Laghi L, Crecchio C, Guerzoni ME, Gobbetti M, Francavilla R: Duodenal and faecal microbiota of celiac children: molecular, phenotype and metabolome characterization. BMC Microbiol. 2011 Oct 4;11:219. doi: 10.1186/1471-2180-11-219. [PubMed:21970810 ]
| Crohn's disease |
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- Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
| Perillyl alcohol administration for cancer treatment |
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- Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
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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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FooDB ID | FDB008055 |
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KNApSAcK ID | C00001254 |
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Chemspider ID | 7760 |
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KEGG Compound ID | C08380 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | 2-Heptanone |
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METLIN ID | Not Available |
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PubChem Compound | 8051 |
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PDB ID | Not Available |
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ChEBI ID | 5672 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00000431 |
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Good Scents ID | rw1002111 |
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References |
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Synthesis Reference | Johnson, J. R.; Hager, F. D. Methyl amyl ketone. Organic Syntheses (1927), 7 60-2. CODEN: ORSYAT ISSN:0078-6209. CAN 21:32500 AN 1927:32500 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | Not Available |
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