Cembrene A

Cembrene A
	Cembrene A
Names
	Preferred IUPAC name (1E,5E,9E,12R)-1,5,9-Trimethyl-12-(prop-1-en-2-yl)cyclotetradeca-1,5,9-triene
	Other names (R,1E,5E,9E)-1,5,9-Trimethyl-12-(prop-1-en-2-yl)cyclotetradeca-1,5,9-triene; Neocembrene-A
Identifiers
CAS Number	31570-39-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82800 ;
ChEMBL	ChEMBL518765;
ChemSpider	4444741;
PubChem CID	5281384;
UNII	2WGK4P4230 ;
	InChI 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;
	SMILES C1(=C\CC/C(=C/C[C@H](C(=C)\C)CCC(=C\CC1)\C)C)\C;
Properties
Chemical formula	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 is 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] Pinus leucodermis tree bark and wood essential oils contain a high percentage of cembrene.^[4]

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. 21: 2653–2658. doi:10.1039/p19720002653.
1 2 Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, Eberhard Breitmaier, page 7. ISBN 978-3-527-31786-8
↑ Graikou, K.; Gortzi, O.; Mantanis, G.; Chinou, I. (2012). "Chemical composition and biological activity of the essential oil from the wood of Pinus heldreichii Christ. var. leucodermis". European Journal of Wood and Wood Products. 70 (5): 615–620. doi:10.1007/s00107-012-0596-9. ISSN 0018-3768.

[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. 21: 2653–2658. doi:10.1039/p19720002653.

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

[4] Graikou, K.; Gortzi, O.; Mantanis, G.; Chinou, I. (2012). "Chemical composition and biological activity of the essential oil from the wood of Pinus heldreichii Christ. var. leucodermis". European Journal of Wood and Wood Products. 70 (5): 615–620. doi:10.1007/s00107-012-0596-9. ISSN 0018-3768.

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References