Periplanone B

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-oxaspiro[bicyclo[8.1.0]undecane-2,2′-oxiran]-6-en-3-one
Other names
(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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/s1 checkY
    Key: KVFSFBCTIZBPRK-KGDVWTLMSA-N checkY
  • 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/s1
    Key: KVFSFBCTIZBPRK-KGDVWTLMBF
  • O=C2[C@]1(OC1)[C@@H]3O[C@@H]3CC(\C=C\[C@H](C(C)C)C2)=C
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).
X markN verify (what is checkYX markN ?)

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.