- Cembrene A
-
Cembrene A 
[R-(E,E,E)]-1,5,9-trimethyl-12-
(1-methylethenyl)-1,5,9-cyclotetradecatrieneOther namesNeocembrene-AIdentifiers CAS number 31570-39-5 PubChem 5281384 ChemSpider 4444741 ChEMBL CHEMBL518765 Jmol-3D images Image 1 - C1(=C\CC/C(=C/C[C@H](C(=C)\C)CCC(=C\CC1)\C)C)\C
- InChI=1/C20H32/c1-16(2)20-14-12-18(4)10-6-8-17(3)9-7-11-19(5)13-15-20/h8,11-12,20H,1,6-7,9-10,13-15H2,2-5H3/b17-8+,18-12+,19-11+/t20-/m0/s1
Key: VWSPQDDPRITBAM-KPGNMOGWBK
Properties Molecular formula C20H32 Molar mass 272.47 g/mol Boiling point 150-152 °C at 0.8 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references Cembrene A, or sometimes neocembrene, is a natural monocyclic diterpene isolated from corals of the genus Nephthea.[1] It is a colorless oil with a faint wax-like odor.
Cembrene A itself has little importance as chemical entity, being a trail pheromone for termites;[2] however, the chemical structure of cembrene is central to a very wide variety of other natural products found both in plants and in animals.[3]
Cembrenes are biosynthesized by macrocyclization of geranylgeranyl pyrophosphate.[3]
References
- ^ Vanderah, David J.; Rutledge, Neal; Schmitz, Francis J.; Ciereszko, Leon S (1978). "Marine natural products: cembrene-A and cembrene-C from a soft coral, Nephthea species". Journal of Organic Chemistry 43 (8): 1614–1616. doi:10.1021/jo00402a040.
- ^ Birch, A. J.; Brown, W. V.; Corrie, J. E. T.; Moore, B. P (1972). "Neocembrene-A, a termite trail pheromone". Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry 21: 2653–2658. doi:10.1039/p19720002653.
- ^ a b Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, Eberhard Breitmaier, page 7. ISBN 978-3527317868
External links
- Cembrene and Casbene Biosynthesis, Queen Mary University of London
Categories:- Diterpenes
- Insect ecology
- Alkenes
- Pheromones
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