Periplanone B
Periplanone B is a pheromone produced by the female American cockroach,[1] Periplaneta americana. It is a sexual attractant to male cockroaches, especially at short ranges.[2]
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| IUPAC name
(1R,2R,5S,6E,10R)-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 | |
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3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| C15H20O3 | |
| Molar mass | 248.322 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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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.
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