Cembrene A

Cembrene A
Names
IUPAC names
[R-(E,E,E)]-1,5,9-trimethyl-12-
(1-methylethenyl)-1,5,9-cyclotetradecatriene
Other names
Neocembrene-A
Identifiers
31570-39-5
3D model (Jmol) Interactive image
ChEBI CHEBI:82800 YesY
ChEMBL ChEMBL518765
ChemSpider 4444741
PubChem 5281384
Properties
C20H32
Molar mass 272.47 g/mol
Boiling point 150 to 152 °C (302 to 306 °F; 423 to 425 K) at 0.8 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

  1. 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.
  2. 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.
  3. 1 2 Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, Eberhard Breitmaier, page 7. ISBN 978-3-527-31786-8
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