| Verbenone | |
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(1R)-cis-4,6,6-Trimethylbicyclo- |
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Other names
Verbenone |
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| Identifiers | |
| CAS number | 80-57-9 |
| UNII | 99S17893UW |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H14O |
| Molar mass | 150.21 g/mol |
| Density | 0.978 g/cm3 |
| Melting point |
6.5 °C |
| Boiling point |
227–228 °C |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Verbenone is a natural organic compound classified as a terpene which 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 has an important role in the control of the Southern pine bark beetle.
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While verbenone is a terpene, more specifically the compound is also 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.[1]
Verbenone can be readily prepared synthetically by the oxidation of the more common terpene α-pinene:[2]
Verbenone can then be converted into chrysanthenone through a photochemical rearrangement reaction:[3]
The Southern pine bark beetle (Dendroctonus frontalis) 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 are produced to keep additional beetles away. 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 hang verbenone pouches on nearby susceptible healthy trees to repel and confuse the beetles.[4]
Because of its pleasant aroma, verbenone (or essential oils high in verbenone content) are used in perfumery, aromatherapy, herbal teas, spices and herbal remedies. The L-isomer is used as a cough suppressant under the name levoverbenone. Verbenone may also have antimicrobial properties.[5]