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
CAS Number	61228-92-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	9065530 ;
PubChem CID	10890266;
UNII	8HV41M9E86 ;
CompTox Dashboard (EPA)	DTXSID4058441 ;
	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 Key: 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/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). verify (what is ?) Infobox references

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]

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]

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. Bibcode:1990JCEco..16.2605O. doi:10.1007/BF00988072. PMID 24264316. S2CID 30323914.
↑ Chow, YF; Wang, SF (1981). "Attraction responses of the American cockroach to synthetic periplanone-B". Journal of Chemical Ecology. 7 (2): 265–272. Bibcode:1981JCEco...7..265C. doi:10.1007/BF00995749. PMID 24420472. S2CID 21794952.
↑ Wood, William F. (1982). "The Sex Pheromone of the Gypsy Moth and the American Cockroach". Journal of Chemical Education. 59 (1): 35–36. Bibcode:1982JChEd..59...35W. doi:10.1021/ed059p35.
↑ 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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[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. Bibcode:1990JCEco..16.2605O. 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. Bibcode:1981JCEco...7..265C. doi:10.1007/BF00995749. PMID 24420472. S2CID 21794952.

[3] Wood, William F. (1982). "The Sex Pheromone of the Gypsy Moth and the American Cockroach". Journal of Chemical Education. 59 (1): 35–36. Bibcode:1982JChEd..59...35W. doi:10.1021/ed059p35.

[Nicolaou-4] 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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History

References