Periplanone B

Periplanone B

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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
CAS Number	61228-92-0 checkY
3D model (JSmol)	Interactive image
ChemSpider	9065530 checkY
ECHA InfoCard
E number
PubChem CID	10890266
UNII	8HV41M9E86 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
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/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
SMILES O=C2[C@]1(OC1)[C@@H]3O[C@@H]3CC(\C=C\[C@H](C(C)C)C2)=C
Properties
Chemical formula	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). ☒N verify (what is checkY☒N ?) Infobox references

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.