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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 | 2012-09-11 22:17:35 UTC |
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Update Date | 2019-07-30 21:50:13 UTC |
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HMDB ID | HMDB0037050 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 1-Isopropyl-2-methylbenzene |
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Description | 1-Isopropyl-2-methylbenzene, also known as O-cymene or O-cymol, belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. 1-Isopropyl-2-methylbenzene is possibly neutral. Outside of the human body, 1-Isopropyl-2-methylbenzene has been detected, but not quantified in, citrus. This could make 1-isopropyl-2-methylbenzene a potential biomarker for the consumption of these foods. 1-Isopropyl-2-methylbenzene, with regard to humans, has been found to be associated with several diseases such as diarrhoea predominant irritable bowel syndrome, pervasive developmental disorder not otherwise specified, ulcerative colitis, and autism; 1-isopropyl-2-methylbenzene has also been linked to the inborn metabolic disorder celiac disease. |
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Structure | |
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Synonyms | Value | Source |
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1-(1-Methylethyl)-2-methylbenzene | HMDB | 1-Methyl,2-N-isopropylbenzene | HMDB | 1-Methyl-2-(1-methylethyl)-benzene | HMDB | 1-Methyl-2-(1-methylethyl)benzene, 9ci | HMDB | 1-Methyl-2-isopropylbenzene | HMDB | 1-Methyl-2-isopropylbenzol | HMDB | 2-Isopropyltoluene | HMDB | Cymene, ortho | HMDB | O-Cymene | HMDB | O-Cymol | HMDB | O-Isopropyltoluene | HMDB | O-Mentha-1,3,5-triene | HMDB | Ortho-cymene | HMDB | Ortho-cymol | HMDB |
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Chemical Formula | C10H14 |
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Average Molecular Weight | 134.2182 |
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Monoisotopic Molecular Weight | 134.109550448 |
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IUPAC Name | 1-methyl-2-(propan-2-yl)benzene |
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Traditional Name | 1-methyl-2-isopropylbenzene |
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CAS Registry Number | 527-84-4 |
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SMILES | CC(C)C1=CC=CC=C1C |
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InChI Identifier | InChI=1S/C10H14/c1-8(2)10-7-5-4-6-9(10)3/h4-8H,1-3H3 |
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InChI Key | WWRCMNKATXZARA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cumenes. These are aromatic compounds containing a prop-2-ylbenzene moiety. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Cumenes |
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Direct Parent | Cumenes |
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Alternative Parents | |
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Substituents | - Phenylpropane
- Cumene
- Toluene
- Aromatic hydrocarbon
- Unsaturated hydrocarbon
- Hydrocarbon
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Biological role: |
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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 | -71.54 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.023 mg/mL at 25 °C | Not Available | LogP | 4.38 | Not Available |
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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 - CI-B (Non-derivatized) | splash10-000f-4900000000-9e95146a0a21b765a8c3 | Spectrum | GC-MS | GC-MS Spectrum - CI-B (Non-derivatized) | splash10-000f-4900000000-9e95146a0a21b765a8c3 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-014l-9800000000-90eced199b00356905aa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0900000000-6b98b0d90b15565d72ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-2900000000-88d6444d760c61b2e23a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbc-9500000000-0280fe47fac120092895 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-e9eba9504e8c693c8893 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-d8e1d54b671cb752329c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00lu-4900000000-4c3e3b6a13cd7c3016ae | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - Breath
- 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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Breath | 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 | Children (1-13 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 | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | 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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Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) non progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Immunoglobulin A nephropathy (IgAN) progressor | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Diarrhea-predominant IBS | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Autism | | details | Feces | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Pervasive Developmental Disorder Not Otherwise Specified | | 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 | Crohn's disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Nonalcoholic fatty liver disease (NAFLD) | | details | Saliva | Detected but not Quantified | Not Quantified | Children (1-13 years old) | Both | Celiac disease | | details |
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Associated Disorders and Diseases |
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Disease References | 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 ]
| Diarrhoea predominant irritable bowel syndrome |
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- Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
| 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 ]
| Ulcerative colitis |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| Crohn's disease |
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- De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
| Celiac disease |
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- Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]
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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 | FDB016032 |
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KNApSAcK ID | C00010974 |
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Chemspider ID | 10253 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 10703 |
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PDB ID | Not Available |
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ChEBI ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Rzepa J, Wojtal L, Staszek D, Grygierczyk G, Labe K, Hajnos M, Kowalska T, Waksmundzka-Hajnos M: Fingerprint of selected Salvia species by HS-GC-MS analysis of their volatile fraction. J Chromatogr Sci. 2009 Aug;47(7):575-80. [PubMed:19772730 ]
- Pertsovskii AL, Stel'makh VA: [Chromatographic determination of orthomenthane hydrocarbons in biological media]. Farmakol Toksikol. 1985 Jan-Feb;48(1):55-6. [PubMed:3979538 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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