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Periplanone B

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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.[3] The stereochemical configuration and first total synthesis were reported by W. Clark Still's group at Columbia University in 1979.[4]

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