Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:51 UTC |
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Update date | 2019-11-26 03:00:46 UTC |
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Primary ID | FDB005805 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Longifolene |
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Description | Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts . |
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CAS Number | 475-20-7 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-longifolen | biospider | (+)-longifolene | biospider | (+)-longofolene | biospider | α-longifolene | biospider | 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene- | biospider | 1,4-Methanoazulene, Junipen | biospider | 4,8,8-trimethyl-9-methylidenedecahydro-1,4-methanoazulene | biospider | D-longifolene | biospider | Junipen | biospider | Junipene | biospider | Kuromatsuen | biospider | Kuromatsuene | biospider | Longifolen | biospider | Longifolene | biospider | Longifolene (=junipene) | biospider |
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Predicted Properties | |
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Chemical Formula | C15H24 |
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IUPAC name | 3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane |
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InChI Identifier | InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3 |
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InChI Key | PDSNLYSELAIEBU-UHFFFAOYSA-N |
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Isomeric SMILES | CC12CCCC(C)(C)C3C(CCC13)C2=C |
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Average Molecular Weight | 204.357 |
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Monoisotopic Molecular Weight | 204.187800773 |
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Classification |
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Description | Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
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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 | Sesquiterpenoids |
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Direct Parent | Sesquiterpenoids |
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Alternative Parents | |
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Substituents | - Longifolane or isolongifolane sesquiterpenoid
- Sesquiterpenoid
- Branched unsaturated hydrocarbon
- Polycyclic hydrocarbon
- Cyclic olefin
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Hydrocarbon
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Boiling Pt : 258 oC | |
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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) | splash10-0a4l-9800000000-39919bcbac1cbe903234 | 2015-03-01 | View Spectrum | Predicted GC-MS | Longifolene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-01s9-2900000000-035dbcf027d0dfba677b | 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 | splash10-0a4i-0090000000-8be5b82f1970df5d0fba | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-1390000000-5b0723496471550d90fb | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00n0-8900000000-96000d2a703ee43023ea | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-d8dbe2f117875c63d9b7 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-b23a97fc2ece08b93c5d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000i-1900000000-023300ca2a969c85df78 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0190000000-957001643af974296779 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-05fr-4940000000-08e8b30216bee8b9d0b7 | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-006x-6900000000-2057ea9054379c9d846d | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-7ccf03fa1149a1e9f55f | 2021-10-21 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0090000000-6efb1ac8bbe4b57b1ab9 | 2021-10-21 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C09699 |
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Pubchem Compound ID | 289151 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 6530 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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CRC / DFC (Dictionary of Food Compounds) ID | KMC00-T:KMC00-T |
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EAFUS ID | Not Available |
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Dr. Duke ID | LONGIFOLENE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003162 |
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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 | Not Available |
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GoodScent ID | rw1020031 |
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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 | 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 | 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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sweet |
- 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.
| rose |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| medical |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| fir needle |
- 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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