Periplanone B
 | |
| Names | |
|---|---|
| IUPAC name
(1S, 2S,5S,10S)-(6E)-8-Methylidene-5-propan-2-ylspiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxirane]-3-one | |
| Other names
(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one | |
| Identifiers | |
61228-92-0  | |
| ChemSpider | 9065530  |
| |
| Jmol-3D images | Image |
| PubChem | 10890266 |
| |
| Properties | |
| Molecular formula |
C15H20O3 |
| Molar mass | 248.32 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| Infobox references | |
Periplanone B is a pheromone produced by the female American cockroach,[1] Periplaneta americana. It is a sexual excitant to male cockroaches, especially at short ranges.[2]
History
The activity of this pheromone was first described in 1952, but it was not until 25 years later that Persoons et al. reported the gross structure of periplanones A and B. The stereochemical configuration and first total synthesis were reported by W. Clark Still's group at Columbia University in 1979.[3]
References
- ↑ Okada, K et al. (September 1990). "Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B". Journal of Chemical Ecology 16 (9): 2605–2614. doi:10.1007/BF00988072.
- ↑ Chow, YF; Wang, SF (1981). "Attraction responses of the American cockroach to synthetic periplanone-B". Journal of Chemical Ecology 7 (2): 265–272. doi:10.1007/BF00995749.
- ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. p. 211. ISBN 3-527-29284-5.