2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00055 |
| Mol. Weight | 204.357 g/mol |
| LogP | 5.14 |
| Water solubility | 0.0000251 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 0 |
| Rotatable Bonds | 6 |
| XLogP3-AA | 6.1 |
| Identifiers | |
|---|---|
| Formula | C15H24 |
| PubChem CID | 5281516 |
| FEMA | 3839 |
| Flavor Profile | None |
| Smiles | C=C/C(C)=C/C/C=C(\C)CCC=C(C)C |
| InChl Key | CXENHBSYCFFKJS-VDQVFBMKSA-N |
| InChl | 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+ |
| CAS Registry Number | 502-61-4, |
| IUPAC Systematic Name | (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Dahurian Angelica | Bai Zhi(白芷) | Angelicae Dahuricae Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Long Pepper | Bi Ba (荜茇) | Piperis Longi Fructus | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Chinese Thorowax Equivalent plant: Bupleurum scorz | Chai Hu(柴胡) | Bupleuri Radix | Minor cold, Pungent, Bitter | Liver, Gallbladder, Lung | View Graph |
| Chuanxiong (Wallich Ligusticum) Equivalent plant | Chuan Xiong (川芎) | Ligusticum chuanxiong Hort | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Clove Tree | Ding Xiang (丁香) | Caryophylli Flos | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Zedoray Rhizome | E Zhu (莪术) | Curcumae Rhizoma | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Common Ginger Dried Rhizome | Gan Jiang (干姜) | Zingiberis Rhizoma | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Lesser Galangal | Gao Liang Jiang (高良姜) | Alpiniae Officinarum Rhizoma | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Chinese Ligusticum Equivalent plant: Ligusticum je | Gao Ben (藁本) | Ligustici Rhizoma Et Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Black Pepper | Hu Jiao (胡椒) | Piperis Fructus | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Bunge Pricklyash Equivalent plant: Zanthoxylum sch | Hua Jiao (花椒) | Zanthoxyli Pericarpium | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Odoriferous Rosewood | Jiang Xiang (降香) | Dalbergiae odoriferae Lignum | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Chinese Ephedra Equivalent plant: Ephedra equiseti | Ma Huang (麻黄) | Ephedrae Herba | Warm, Pungent, Slightly Bitter | Lung, Bladder | View Graph |
| Myrrh | Mo Yao (没药) | Myrrha | Neutral, Pungent, Bitter | Spleen, Liver, Heart, Kidney | View Graph |
| Cassiabarktree | Rou Gui (肉桂) | Cinnamomi Cortex | Hot, Sweet, Pungent | Liver, Heart, Spleen, Kidney | View Graph |
| Cnidium monnieri | She Chuang Zi(蛇床子) | Common Cnidium | Warm,Pungent,Bitter | Lung,Spleen,Liver | View Graph |
| Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Evodia rutaecarpa | Wu Zhu Yu(吴茱萸) | Medicinal Evodia Equivalent plant: Evodia rutaecar | Pungent, bitter, hot | Liver, spleen,stomach | View Graph |
| Siebold Wildginger Equivalent plant: Asarum hetero | Xi Xin (细辛) | Asari Radix Et Rhizoma | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Haichow Elsholtzia | Xiang Ru (香薷) | Moslae Herba | Minor Warm,Pungent | Lung, Spleen, Stomach | View Graph |
| Lily Magnolia Buds Equivalent plant: Magnolia lili | Xin Yi (辛夷) | Magnoliae Flos | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Common Goldenrod | Yi Zhi Huang Hua(一枝黄花) | Solidaginis Herba | Cool, Bitter, Pungent | Liver, Lung | View Graph |
| Perilia Fruit | Zi Su Zi (紫苏子) | Perillae Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Sandalwood | Tan Xiang(檀香) | Santali Albi Lignum | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as
four stereoisomers that differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). The beta isomer exists as two stereoisomers about the geometry of its central double bond.
α-farnesene act as sexual or trail pheromones in several insect orders, including many ant genera. α-farnesene and ocimenes are common volatile terpenes of HIPVs in tea plants. As an apple odorant, a-farnesene has been implicated in several aspects of codling moth host-finding behavior. a-Farnesene occurs in the peel and wax of apple fruit. a-Farnesene has been thought to be involved in the development of superficial scald on apples.
a-Farnesene,one of the simplest acyclic sesquiterpenes, is a compound abundantly located in apple peels with high-functional performance in plant defense.Besides, a-farnesene also works as an alarm pheromone to signal danger in aphids and termites, and as a molecule implicated in the orientation of worker fire ants.
a-Farnesene biosynthesis is initiated by the formation of isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) precursors issued from the mevalonate (MVA) pathway in eukaryotes, with hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase and the FPP branch-point as the two main regulation sites in the pathway.
Alpha-Farnesene accumulates at relatively high levels in the pear peel during low temperature storage.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1 Zeng L, Liao Y, Li J, et al. α-Farnesene and ocimene induce metabolite changes by volatile signaling in neighboring tea (Camellia sinensis) plants[J]. Plant Science, 2017, 264: 29-36.
2 Attygalle A B, Morgan E D. Trail pheromone of the ant Tetramorium caespitum L[J]. Naturwissenschaften, 1983, 70(7): 364-365.
3 Vander Meer R K. Semiochemicals and the red imported fire ant (Solenopsis invicta Buren)(Hymenoptera: Formicidae)[J]. Florida entomologist, 1983: 139-161.
4 Detrain C, Pasteels J M, Braekman J C, et al. (Z, E)-α-farnesene, main constitutent of the hypertrophied Dufour's gland of the major workers ofPheidole pallidula (Formicidae)[J]. Experientia, 1987, 43(3): 345-346.
5 Murray K E, Huelin F E, Davenport J B. Occurrence of farnesene in the natural coating of apples[J]. Nature, 1964, 204(4953): 80.
6 Huelin F E, Coggiola I M. Superficial scald, a functional disorder of stored apples. IV.—Effect of variety, maturity, oiled wraps and diphenylamine on the concentration of a‐farnesene in the fruit[J]. Journal of the Science of Food and Agriculture, 1968, 19(6): 297-301.
7 Landolt P J, Brumley J A, Smithhisler C L, et al. Apple fruit infested with codling moth are more attractive to neonate codling moth larvae and possess increased amounts of (E, E)-α-farnesene[J]. Journal of Chemical Ecology, 2000, 26(7): 1685-1699.
8 Nieuwenhuizen N J, Green S, Atkinson R G. Floral sesquiterpenes and their synthesis in dioecious kiwifruit[J]. Plant signaling & behavior, 2010, 5(1): 61-63.
9 Yang T, Stoopen G, Yalpani N, et al. Metabolic engineering of geranic acid in maize to achieve fungal resistance is compromised by novel glycosylation patterns[J]. Metabolic engineering, 2011, 13(4): 414-425.
10 Šobotník J, Hanus R, Kalinová B, et al. (E, E)-α-farnesene, an alarm pheromone of the termite Prorhinotermes canalifrons[J]. Journal of chemical ecology, 2008, 34(4): 478-486.
11 Suckling D M, Stringer L D, Bunn B, et al. Trail pheromone disruption of red imported fire ant[J]. Journal of chemical ecology, 2010, 36(7): 744-750.
12 Withers S T, Keasling J D. Biosynthesis and engineering of isoprenoid small molecules[J]. Applied microbiology and biotechnology, 2007, 73(5): 980-990.
13 Yang X, Nambou K, Wei L, et al. Heterologous production of α-farnesene in metabolically engineered strains of Yarrowia lipolytica[J]. Bioresource technology, 2016, 216: 1040-1048.
14 Golding J B, McGlasson W B, Wyllie S G. Relationship between production of ethylene and α-farnesene in apples, and how it is influenced by the timing of diphenylamine treatment[J]. Postharvest biology and technology, 2001, 21(2): 225-233.
15 Røstelien T, Borg-Karlson A K, Mustaparta H. Selective receptor neurone responses to E-β-ocimene, β-myrcene, E, E-α-farnesene and homo-farnesene in the moth Heliothis virescens, identified by gas chromatography linked to electrophysiology[J]. Journal of Comparative Physiology A, 2000, 186(9): 833-847.
16 Aprea E, Charles M, Endrizzi I, et al. Sweet taste in apple: the role of sorbitol, individual sugars, organic acids and volatile compounds[J]. Scientific Reports, 2017, 7: 44950.
17 Yazdani N, Arzani K, Mostofi Y, et al. α-Farnesene and antioxidative enzyme systems in Asian pear (Pyrus serotina Rehd.) fruit[J]. Postharvest biology and technology, 2011, 59(3): 227-231.
18 https://en.wikipedia.org/wiki/Farnesene