Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:32 UTC |
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Update date | 2020-09-17 15:32:36 UTC |
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Primary ID | FDB014895 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | (3E,6E)-alpha-Farnesene |
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Description | Trans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-Farnesene, belongs to the class of organic compounds known as sesquiterpenoids. 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-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. α-Farnesene and β-Farnesene are isomers, differing by the location of one double bond. β-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260a0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots. |
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CAS Number | 502-61-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(3E,6E)-alpha-Farnesene | ChEBI | (3E,6E)-a-Farnesene | Generator | (3E,6E)-Α-farnesene | Generator | a-Farnesene | Generator | Α-farnesene | Generator | (E,E)-Farnesene | HMDB | trans-Farnesene | HMDB | 3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene | HMDB | alpha-trans,trans-Farnesene | HMDB | trans,trans-alpha-Farnesene | HMDB | alpha-Farnesene | MeSH | (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene | HMDB | (E,E)-alpha-Farnesene | HMDB | (E,E)-α-Farnesene | HMDB | 3,7,11-Trimethyl-1,3,6,10-dodecatetraene | HMDB | Farnesene | HMDB | trans,trans-α-Farnesene | HMDB | trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene | HMDB | trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene | HMDB | trans-alpha-Farnesene | HMDB | trans-α-Farnesene | HMDB | -e,e-Farnesene | HMDB | -trans-Farnesene | HMDB | (3E,6E)-α-Farnesene | biospider | (3e,6e)-a-Farnesene | Generator | (3e,6e)-α-farnesene | Generator | (e,e)-a-Farnesene | Generator | (e,e)-alpha-Farnesene | ChEBI | (e,e)-α-farnesene | Generator | α-e,e-Farnesene | biospider | α-trans-Farnesene | biospider | α-trans,trans-Farnesene | biospider | 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (E,E)- | biospider | 3,7,11-Trimethyl-(e,e)-1,3,6,10-dodecatetraene | HMDB | Alph | HMDB |
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Predicted Properties | |
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Chemical Formula | C15H24 |
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IUPAC name | (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene |
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InChI Identifier | InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+ |
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InChI Key | CXENHBSYCFFKJS-VDQVFBMKSA-N |
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Isomeric SMILES | CC(C)=CCC\C(C)=C\C\C=C(/C)C=C |
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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 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 | - Farsesane sesquiterpenoid
- Sesquiterpenoid
- Alkatetraene
- Branched unsaturated hydrocarbon
- Unsaturated aliphatic hydrocarbon
- Unsaturated hydrocarbon
- Olefin
- Acyclic olefin
- Hydrocarbon
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Biological location: Source: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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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 | C 88.16%; H 11.84% | DFC |
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Melting Point | < 25 oC | |
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Boiling Point | Not Available | |
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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) | splash10-0006-9300000000-3317cba9629f9379052f | 2015-03-01 | View Spectrum | Predicted GC-MS | (3E,6E)-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0673-9800000000-2417bd57042b291e594e | Spectrum | Predicted GC-MS | (3E,6E)-alpha-Farnesene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | (3E,6E)-alpha-Farnesene, 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 | splash10-0a4i-3690000000-313b913d532cd4decec1 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0pw9-9710000000-078e5a8d7e85822b7c0c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uxr-9100000000-3d3f85f913cafb612d5c | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0090000000-6d4cdcd69849df029e45 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0190000000-e363a25bab51e774a592 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0kg9-4900000000-b4cda282a594b52f2539 | 2016-08-04 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0190000000-fa0c676eabe0c49e322b | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0390000000-0d353a60a5a97cd9c1a3 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-014i-4900000000-9f5bab6c0c653c72230e | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-060s-7910000000-05be940f3488abb12fe8 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a7l-9300000000-a54209dd2c1271d1d7d7 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05ru-9000000000-a7b8e3b259690a16a441 | 2021-09-22 | View Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 4444849 |
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ChEMBL ID | CHEMBL3182226 |
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KEGG Compound ID | C09665 |
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Pubchem Compound ID | 5281516 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 10280 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB36066 |
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CRC / DFC (Dictionary of Food Compounds) ID | JXF60-O:JXF61-P |
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EAFUS ID | 1333 |
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Dr. Duke ID | TRANS-ALPHA-FARNESENE|FARNESENE|TRANS,TRANS-ALPHA-FARNESENE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00003130 |
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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 | 502-61-4 |
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GoodScent ID | rw1044061 |
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SuperScent ID | 5281516 |
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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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pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | pheromone | 26013 | A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. | DUKE |
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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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wood |
- 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
| sweet |
- 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
| lavender |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| lime |
- Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
| citrus |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| bergamot |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| myrrh |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| neroli |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| green |
- 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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