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Periplanone B

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Periplanone B
Names
IUPAC name (5E)-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one
Systematic IUPAC name (1R,2R,5S,6E,10R)-8-Methylidene-5-(propan-2-yl)-11-oxaspiroundecane-2,2′-oxiran]-6-en-3-one
Other names (1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H20O3/c1-9(2)11-5-4-10(3)6-12-14(18-12)15(8-17-15)13(16)7-11/h4-5,9,11-12,14H,3,6-8H2,1-2H3/b5-4+/t11-,12+,14+,15-/m0/s1Key: KVFSFBCTIZBPRK-KGDVWTLMSA-N
  • InChI=1/C15H20O3/c1-9(2)11-5-4-10(3)6-12-14(18-12)15(8-17-15)13(16)7-11/h4-5,9,11-12,14H,3,6-8H2,1-2H3/b5-4+/t11-,12+,14+,15-/m0/s1Key: KVFSFBCTIZBPRK-KGDVWTLMBF
SMILES
  • O=C21(OC1)3O3CC(\C=C\(C(C)C)C2)=C
Properties
Chemical formula C15H20O3
Molar mass 248.322 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Periplanone B is a pheromone produced by the female American cockroach, Periplaneta americana. It is a sexual attractant to male cockroaches, especially at short ranges.

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.

References

  1. 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. PMID 24264316. S2CID 30323914.
  2. 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. PMID 24420472. S2CID 21794952.
  3. 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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