Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:43 UTC |
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Update date | 2020-09-17 15:32:28 UTC |
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Primary ID | FDB000812 |
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Secondary Accession Numbers | - FDB003847
- FDB003828
- FDB003835
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Chemical Information |
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FooDB Name | p-Mentha-1,3,5,8-tetraene |
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Description | para-Mentha-1,3,5,8-tetraene, also known as Dehydro-p-cymene, p-alpha-dimethyl-styrene, Habanene or p-Cymenene, belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. Dehydro-p-cymene is biochemically a monocyclic monoterpenoid as it is synthesized via isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Dehydro-p-cymene is a hydrophobic, neutral molecule that is insoluble in water. It exists as a clear, colorless oil. Dehydro-p-cymene has a herbaceous, leathery, peppery odor with notes of elemi oil and thyme, as well as a touch of citrus. It has an oregano, clove, basalmic, spicy taste. Dehydro-p-cymene is used as a flavoring agent for Italian dishes and for enhancing habanero spices. Dehydro-p-cymene is found in the highest concentration within star anises but it has also been detected in several different foods, such as lemons, coffee, dill, evergreen blackberries, parsley, citrus, sage, spearmint and pepper. |
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CAS Number | 1195-32-0 |
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Structure | |
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Synonyms | Synonym | Source |
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4-Isopropenyltoluene | MeSH | 1-Isopropenyl-4-methylbenzene | HMDB | 1-Methyl-4-(1-methylethenyl)-benzene | HMDB | 1-Methyl-4-(1-methylethenyl)benzene | HMDB | 1-Methyl-4-(1-methylethenyl)benzene, 9ci | HMDB | 1-Methyl-4-isopropenylbenzene | HMDB | 1-Methyl-4alpha-methylstyrene | HMDB | 2-(4-Methylphenyl)propene | HMDB | 2-(P-Methylphenyl)propene | HMDB | 2-P-Tolylpropene | HMDB | 4-Methyl-alpha-methylstyrene | HMDB | 4-Methylisopropenylbenzene | HMDB | alpha,4-Dimethylstyrene | HMDB | alpha,P-Dimethylstyrene | HMDB | alpha-Dimethyl-P-styrene | HMDB | alpha-Methyl-P-methylstyrene | HMDB | alpha-P Dimethylstyrene | HMDB | Cymenene | HMDB | dehydro-P-Cymene | HMDB | FEMA 3144 | HMDB | Ghl.PD_Mitscher_leg0.317 | HMDB | Isopropenyl toluene c | HMDB | Methyl-4-(1-methylethenyl)-benzene | HMDB | Methyl-P-isopropenylbenzene | HMDB | P,a-Dimethylstyrene, 8ci | HMDB | P,alpha-Dimethyl-styrene | HMDB | P,alpha-Dimethylstyrene | HMDB | P,alpha-Dimethylstyrol | HMDB | P-alpha-Dimethyl-styrene | HMDB | P-alpha-Dimethylstyrene | HMDB | P-Cymenene | HMDB | P-Isopropenyl toluene | HMDB | P-Isopropenyltoluene | HMDB | P-Methyl-alpha-methylstyrene | HMDB | Para- alpha-dimethylstyrene | HMDB | α-dimethyl-p-styrene | biospider | α,4-Dimethylstyrene | biospider | α,p-dimethylstyrene | biospider | 1-Methyl-4-(1-methylethenyl)benzene, 9CI | db_source | 1-methyl-4α-methylstyrene | biospider | 2-(p-Methylphenyl)propene | biospider | 2-p-Tolylpropene | biospider | 4-Methyl-α-methylstyrene | biospider | Alpha-methyl-p-methylstyrene | biospider | Benzene, 1-methyl-4-(1-methylethenyl)- | biospider | Dehydro-p-cymene | biospider | Dimethylstyrene, p-alpha- | biospider | ghl.PD_Mitscher_leg0.317 | biospider | Isopropenyltoluene, p- | biospider | Methyl-p-isopropenylbenzene | biospider | P-alpha-dimethylstyrene | biospider | p-Cymenene | db_source | P-isopropenyl toluene | biospider | p-Isopropenyltoluene | db_source | P-methyl-α-methylstyrene | biospider | P,α-dimethylstyrene | biospider | P,α-dimethylstyrol | biospider | p,a-Dimethylstyrene, 8CI | db_source | P,alpha-dimethylstyrene | biospider | Para- α-dimethylstyrene | biospider | Styrene, p-alpha-dimethyl- | biospider | Styrene, p,α-dimethyl- | biospider |
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Predicted Properties | |
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Chemical Formula | C10H12 |
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IUPAC name | 1-methyl-4-(prop-1-en-2-yl)benzene |
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InChI Identifier | InChI=1S/C10H12/c1-8(2)10-6-4-9(3)5-7-10/h4-7H,1H2,2-3H3 |
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InChI Key | MMSLOZQEMPDGPI-UHFFFAOYSA-N |
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Isomeric SMILES | CC(=C)C1=CC=C(C)C=C1 |
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Average Molecular Weight | 132.2023 |
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Monoisotopic Molecular Weight | 132.093900384 |
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Classification |
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Description | Belongs to the class of organic compounds known as phenylpropenes. Phenylpropenes are compounds containing a phenylpropene moiety, which consists of a propene substituent bound to a phenyl group. |
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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 | Phenylpropenes |
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Direct Parent | Phenylpropenes |
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Alternative Parents | |
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Substituents | - Phenylpropene
- Styrene
- Toluene
- Aromatic hydrocarbon
- Branched unsaturated hydrocarbon
- Cyclic olefin
- Unsaturated hydrocarbon
- Olefin
- 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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Process | Naturally occurring process: |
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Role | Biological 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 90.85%; H 9.15% | DFC |
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Melting Point | Mp -20° | DFC |
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Boiling Point | Bp 184-185° | DFC |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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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 | Not Available | |
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Refractive Index | Not Available | |
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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) | splash10-014i-7900000000-8a35d379c53b742012db | 2015-03-01 | View Spectrum | Predicted GC-MS | p-Mentha-1,3,5,8-tetraene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-5900000000-42122b872bf255e28667 | Spectrum | Predicted GC-MS | p-Mentha-1,3,5,8-tetraene, 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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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0900000000-1a859e9677580ea17b57 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-1900000000-2fd4472dcad1e8a7e949 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0159-7900000000-c9e2399b68bfd80c5f89 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-564cd5c06312dcea67ff | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-abfffa532b094cd93869 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0159-3900000000-f77c6849e823907a8ecf | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-0900000000-b6dbb79105fa765a1a39 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-e787ac89e5bc523fe920 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-4900000000-f20794dba4e302324ade | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-1900000000-7a77bd4827fc7193683c | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9300000000-8f432d1b83b7ee6d6dc8 | 2021-09-25 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004i-9000000000-b7bc284e37a86692377c | 2021-09-25 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 56173 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 62385 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB29641 |
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CRC / DFC (Dictionary of Food Compounds) ID | BHZ62-U:BHZ62-U |
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EAFUS ID | 1032 |
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Dr. Duke ID | ALPHA-METHYL-P-METHYL-STYRENE|P-ALPHA-DIMETHYLSTYRENE|ALPHA-DIMETHYLSTYRENE|1-METHYL-4-ISOPROPENYL-BENZENE|4-ISOPROPENYL-TOLUENE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00010905 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | 1195-32-0 |
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GoodScent ID | rw1018551 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | |
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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 | Not Available |
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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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gasoline |
- 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
| citrus |
- 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
| pine |
- 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
| phenolic |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| spicy |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| styrene |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| clove |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| guaiacol |
- 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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