Frontalin
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
(1S,5R)-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H14O2 | |
| Molar mass | 142.20 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Frontalin is a naturally occurring organic compound. It is a terpenoid and acetal that functions as a pheromone in bark beetles and elephants.
Frontalin acts as an insect pheromone in bark beetles of the genus Dendroctonus, including Dendroctonus frontalis (Southern Pine Beetle) and Dendroctonus brevicomis (Western Pine Beetle), as well as the Mountain Pine Beetle. The biologically active form is predominantly (-)-frontalin.[1] However, (+)-frontalin also occurs in some cases. In Dendroctonus frontalis, the female mainly produces (-)-frontalin, the male mainly (+)-frontalin. In Dendroctonus rufipennis the distribution is reversed.[2]
In addition to its role in insect pheromones, frontalin also serves as a pheromone in Asian elephants. It is secreted by adult male elephants during musth, with secretion levels increasing with age. It signals mating readiness, particularly attracting females who are also in the receptive phase of their sexual cycle.[3]