Grandisol is a natural organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the molecular formula C₁₀H₁₈O. It is a monoterpene

Monoterpene

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings...

 containing a cyclobutane

Cyclobutane

Cyclobutane is an organic compound with the formula 4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes...

 ring, an alcohol

Alcohol

In chemistry, an alcohol is an organic compound in which the hydroxy functional group is bound to a carbon atom. In particular, this carbon center should be saturated, having single bonds to three other atoms....

 group, an alkene

Alkene

In organic chemistry, an alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon-to-carbon double bond...

 group and two chiral

Chirality (chemistry)

A chiral molecule is a type of molecule that lacks an internal plane of symmetry and thus has a non-superimposable mirror image. The feature that is most often the cause of chirality in molecules is the presence of an asymmetric carbon atom....

 centers (one of which is quaternary).

Grandisol is a pheromone

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 outside the body of the secreting individual to impact the behavior of the receiving individual...

 primarily important as the sex attractant of the cotton boll weevil (Anthonomus grandis), from which it gets its name. It is also a pheromone for other related insects. The cotton boll weevil is an agricultural pest that can cause significant economic damage if not controlled. Grandisol is the major constituent of the mixture known as grandlure, which is used to protect cotton crops from the boll weevil.

Synthesis

Grandisol was first isolated, identified, and synthesized by J. Tumlinson et al. at Mississippi State University in 1969. The most recent and highest yielding synthetic route to grandisol was reported in January 2010 by a group of chemists at Furman University

Furman University

Furman University is a selective, private, coeducational, liberal arts college in Greenville, South Carolina, United States. Furman is one of the oldest, and more selective private institutions in South Carolina...

. Though enantioselective syntheses have been reported, racemic grandisol has proven equally effective at attracting boll weevils as the natural enantiomer, rendering moot the need for enantioselective syntheses for agricultural purposes.