Periplanone B is a
pheromone
A pheromone () is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to affect the behavio ...
produced by the female American cockroach, ''
Periplaneta americana
The American cockroach (''Periplaneta americana'') is the largest species of common cockroach, and often considered a pest. In certain regions of the U.S. it is colloquially known as the waterbug, though it is not a true waterbug since it is not ...
''. 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
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The study of stereochemistry focuses on the relationships between stereoisomers, which are defined ...
configuration and first
total synthesis
Total synthesis, a specialized area within organic chemistry, focuses on constructing complex organic compounds, especially those found in nature, using laboratory methods. It often involves synthesizing natural products from basic, commercially ...
were reported by
W. Clark Still
William Clark Still (born 1946) is an American organic chemistry, organic chemist. As a distinguished professor at Columbia University, Clark Still made significant contributions to the field of organic chemistry, particularly in the areas of na ...
's group at
Columbia University
Columbia University in the City of New York, commonly referred to as Columbia University, is a Private university, private Ivy League research university in New York City. Established in 1754 as King's College on the grounds of Trinity Churc ...
in 1979.
References
Insect pheromones
Epoxides
Sesquiterpenes
Spiro compounds
Ketones
Conjugated dienes
Vinylidene compounds
{{Ketone-stub