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Cembrene A

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
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
  • 31570-39-5 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82800 Y
ChEMBL
  • ChEMBL518765
ChemSpider
  • 4444741
  • 5281384
UNII
  • 2WGK4P4230 Y
  • 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
  • C1(=C\CC/C(=C/C[C@H](C(=C)\C)CCC(=C\CC1)\C)C)\C
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).

Cembrene A itself has little importance as a 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 edit

  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.
  3. ^ a b Terpenes: Flavors, Fragrances, Pharmaca, Pheromones, Eberhard Breitmaier, page 7. ISBN 978-3-527-31786-8

cembrene, sometimes, neocembrene, natural, monocyclic, diterpene, isolated, from, corals, genus, nephthea, colorless, with, faint, like, odor, names, preferred, iupac, name, trimethyl, prop, cyclotetradeca, triene, other, names, trimethyl, prop, cyclotetradeca. 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 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 trieneNeocembrene A Identifiers CAS Number 31570 39 5 Y 3D model JSmol Interactive image ChEBI CHEBI 82800 Y ChEMBL ChEMBL518765 ChemSpider 4444741 PubChem CID 5281384 UNII 2WGK4P4230 Y 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 s1Key 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 itself has little importance as a 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 edit 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 a b Terpenes Flavors Fragrances Pharmaca Pheromones Eberhard Breitmaier page 7 ISBN 978 3 527 31786 8 Retrieved from https en wikipedia org w index php title Cembrene A amp oldid 1049484967, wikipedia, wiki, book, books, library,

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