Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:12:09 UTC |
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Update date | 2019-11-26 03:12:30 UTC |
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Primary ID | FDB015966 |
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Secondary Accession Numbers | |
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Chemical Information |
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FooDB Name | Terpinolene |
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Description | Terpinolene, also known as alpha-terpinolene or isoterpinene, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Thus, terpinolene is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Terpinolene. |
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CAS Number | 586-62-9 |
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Structure | |
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Synonyms | Synonym | Source |
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1,4(8)-p-Menthadiene | ChEBI | 1-Methyl-4-(1-methylethylidene)-1-cyclohexene | ChEBI | 1-Methyl-4-(1-methylethylidene)cyclohexene | ChEBI | 4-Isopropylidene-1-methylcyclohexene | ChEBI | alpha-Terpinolene | ChEBI | Isoterpinene | ChEBI | Terpinolen | ChEBI | a-Terpinolene | Generator | Α-terpinolene | Generator | 1,4(8)-Terpadiene | HMDB | 1-Methyl-4-(1-methylethylidene)-cyclohexene | HMDB | 1-Methyl-4-(1-methylethylidene)cyclohexene, 9ci | HMDB | 1-Methyl-4-(propan-2-ylidene)cyclohexene | HMDB | 1-Methyl-4-isopropylidene-1-cyclohexene | HMDB | 4-Isopropylidene-1-methyl-cyclohexene | HMDB | alpha -Terpinolene | HMDB | Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9ci) | HMDB | FEMA 3046 | HMDB | p-Mentha-1,4(8)-diene | PhytoBank | Terpinolene | PhytoBank | delta-Terpinene | PhytoBank | δ-Terpinene | PhytoBank | α-Terpinolene | biospider | 1-Methyl-4-(1-methylethylidene)cyclohexene, 9CI | db_source | Cyclohexene, 1-methyl-4-(1-methylethylidene)- | biospider | Cyclohexene, 3-methyl-6-(1-methylethylidene)- (9CI) | biospider | α-terpinolene | Generator |
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Predicted Properties | |
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Chemical Formula | C10H16 |
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IUPAC name | 1-methyl-4-(propan-2-ylidene)cyclohex-1-ene |
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InChI Identifier | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4H,5-7H2,1-3H3 |
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InChI Key | MOYAFQVGZZPNRA-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)=C1CCC(C)=CC1 |
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Average Molecular Weight | 136.238 |
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Monoisotopic Molecular Weight | 136.125200515 |
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Classification |
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Description | Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Menthane monoterpenoids |
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Alternative Parents | |
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Substituents | - P-menthane monoterpenoid
- Monocyclic monoterpenoid
- Branched unsaturated hydrocarbon
- Cycloalkene
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homomonocyclic compound
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Molecular Framework | Aliphatic homomonocyclic compounds |
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External Descriptors | |
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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 | Industrial application: Biological role: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | C 88.16%; H 11.84% | DFC |
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Melting Point | < 25 oC | |
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Boiling Point | Bp 186° | DFC |
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Experimental Water Solubility | 0.0095 mg/mL at 23 oC | LI,J et al.(1998) |
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Experimental logP | 4.47 | LI,J ET AL (1998) |
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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 | d2020 0.86 | DFC |
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Refractive Index | n20D 1.4900 | 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) | splash10-0006-9400000000-2d00513ea08f32f70cc4 | 2014-09-20 | View Spectrum | GC-MS | Terpineolene, non-derivatized, GC-MS Spectrum | splash10-009f-9400000000-68d00c428f3eca0ec8a8 | Spectrum | GC-MS | Terpineolene, non-derivatized, GC-MS Spectrum | splash10-001l-9400000000-960c0e59a9b4fbc2f209 | Spectrum | GC-MS | Terpineolene, non-derivatized, GC-MS Spectrum | splash10-009f-9400000000-68d00c428f3eca0ec8a8 | Spectrum | GC-MS | Terpineolene, non-derivatized, GC-MS Spectrum | splash10-001l-9400000000-960c0e59a9b4fbc2f209 | Spectrum | GC-MS | Terpineolene, non-derivatized, GC-MS Spectrum | splash10-0006-9500000000-3a9b5aafe573ed72e592 | Spectrum | Predicted GC-MS | Terpineolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-006x-9300000000-9316ff5aec80ce021334 | Spectrum | Predicted GC-MS | Terpineolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Terpineolene, 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 | splash10-000i-3900000000-b14825d366b8c8e2ab12 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000j-9500000000-18b9e19b4b2f2fd07710 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-1000-9100000000-59a2560a612381b96a85 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-954e07bd601b6ad95425 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-e9d35affdc69e9aca942 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014u-6900000000-e560043bc5cf9af10365 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000b-9400000000-7485c8b1e120c014c1c4 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-055f-9100000000-1239888ed93266e025ce | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00ou-9000000000-c37bc4fa72e3458af8e0 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0900000000-a013b4ae27f975ab5621 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014l-8900000000-4cdb68ef9159fc3b02c7 | 2021-09-23 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 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 | 10979 |
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ChEMBL ID | CHEMBL454697 |
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KEGG Compound ID | C06075 |
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Pubchem Compound ID | 11463 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 9457 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36994 |
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CRC / DFC (Dictionary of Food Compounds) ID | KLQ41-R:KLQ41-R |
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EAFUS ID | 3610 |
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Dr. Duke ID | TERPINOLENE|ALPHA-TERPINOLENE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000861 |
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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 | 586-62-9 |
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GoodScent ID | rw1007171 |
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SuperScent ID | 11463 |
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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 | Descriptor | ID | Definition | Reference |
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Allelochemic | | A chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses. | DUKE | Anti feedant | | A substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage. | DUKE | Anti-nitrosaminic | | An agent that inhibits the formation of nitrosamines, carcinogenic compounds. It plays a biological role in cancer prevention, with therapeutic applications in reducing the risk of tobacco-related and other cancers. Key medical uses include chemoprevention and protection against carcinogenic exposures. | DUKE | Anti-oxidant | 22586 | An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects. | DUKE | Deodorant | | A substance that removes or conceals unpleasant smells, especially bodily odors, playing a hygienic role in reducing sweat-induced bacteria growth, with therapeutic applications in managing body odor disorders, and key medical uses in treating hyperhidrosis and bromhidrosis. | DUKE | Name | 48318 | flavor | DUKE | Fungicide | 24127 | An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage. | DUKE | Perfumery | 48318 | The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties. | DUKE | Pesticide | 25944 | An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections. | DUKE | Sedative | 35717 | An agent that calms nervous activity, reducing anxiety and inducing relaxation. Its biological role is to slow down brain function, promoting sleep and relieving stress. Therapeutically, sedatives are used to manage insomnia, anxiety disorders, and seizures, as well as to prepare patients for medical procedures. | CHEBI |
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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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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
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| plastic |
- 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
| fresh |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| sweet |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| citrus |
- 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). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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