| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:06:00 UTC |
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| Update date | 2020-09-17 15:33:45 UTC |
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| Primary ID | FDB003887 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | (E)-alpha-Bergamotene |
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| Description | α-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are four known Bergamotene isomers including α-cis-, α-trans-, β-cis- and β-trans-bergamotene. α-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295). |
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| CAS Number | Not Available |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C15H24 |
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| IUPAC name | (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene |
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| InChI Identifier | InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1 |
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| InChI Key | YMBFCQPIMVLNIU-KFWWJZLASA-N |
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| Isomeric SMILES | CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2 |
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| Average Molecular Weight | 204.3511 |
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| Monoisotopic Molecular Weight | 204.187800768 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. |
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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 | Bicyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Pinane monoterpenoid
- Bicyclic monoterpenoid
- 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 | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | Not Available |
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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-1390000000-d6a0ba11c5a26587cd86 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0aor-4940000000-9dc882467486d9fdf061 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-5900000000-ea9024d4d9b8c46f7756 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-1d073790940a713722d2 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0090000000-de5ae459f3052d9744b7 | 2016-08-03 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0fy9-3910000000-729cba2ca70dcf19f20f | 2016-08-03 | 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 | splash10-0uxr-0790000000-5f2697dd150bf0825ae5 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-060r-2920000000-b37f23a73e76ccb77633 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-3900000000-bdedd611b0ff9d625863 | 2021-10-21 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-069r-9000000000-b2a695a52a29c98c4260 | 2021-10-21 | View Spectrum |
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| NMR | Not Available |
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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 | Not Available |
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| Pubchem Compound ID | Not Available |
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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 | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | (E)-ALPHA-BERGAMOTENE|(E)-ALPHA-BERGAMOTTENE|ALPHA-TRANS-BERGAMOTENE|TRANS-ALPHA-BERGAMOTENE |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00021903 |
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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 | Not Available |
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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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| 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 | Not Available |
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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 |
- Barry B. Snider and Richard B. Beal, “Total synthesis of sesquiterpenes via intramolecular ketene cycloadditions. Isocomene .alpha.-cis- and .alpha.-trans-bergamotenes. An approach to seychellene,” The Journal of Organic Chemistry 53, no. 19 (1988): 4508-4515. PDF [Structure]
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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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