Verbenone
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IUPAC name
(1R)-cis-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
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| Other names
Verbenone
2-Pinen-4-one |
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3D model (JSmol)
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| ECHA InfoCard | 100.001.176 | ||
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PubChem CID
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| Properties | |||
| C10H14O | |||
| Molar mass | 150.22 g·mol−1 | ||
| Density | 0.978 g/cm3 | ||
| Melting point | 6.5 °C (43.7 °F; 279.6 K) | ||
| Boiling point | 227 to 228 °C (441 to 442 °F; 500 to 501 K) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |||
Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle.
Verbenone is a monoterpene, to be specific a bicyclic ketone terpene. It is the primary constituent of the oil of Spanish verbena, hence its name; it is also found in the oil of rosemary. It is nearly insoluble in water, but miscible with most organic solvents.
Verbenone can be readily prepared synthetically by the oxidation of the more common terpene α-pinene:
Verbenone can then be converted into chrysanthenone through a rearrangement reaction:
The southern pine beetle (Dendroctonus frontalis), a bark beetle, is a major threat to pine trees in the southeastern United States. Its reproductive cycle is controlled by varying ratios of certain natural chemicals, including verbenone. To reproduce, pine bark beetles aggregate in large numbers in their host pine trees. At the beginning of an attack, various chemicals produced by infested trees and by the beetles attract additional beetles of the same species. When the numbers of adults and larvae approach the maximum that the tree can support, antiaggregation signal chemicals, i.e., verbenone, are produced, reducing the likelihood that additional beetles will land and attack the tree. Forest managers frequently try to control infestations of the Southern pine bark beetle by cutting down and sometimes burning infested trees and nearby healthy trees. They then place verbenone formulations on nearby susceptible healthy trees to repel and confuse the beetles.
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Wikipedia