(S)-Ipsdienol
Chemical compound
From Wikipedia, the free encyclopedia
(S)-Ipsdienol is a terpene alcohol. It is one of the major aggregation pheromones of the bark beetle. It was first identified from Ips confusus, in which it is believed to be a principle sex attractant.[1] It is suggested that the compound plays a role in interspecies communication between Ips latidens and Ips ini, facilitating reductions in competition for breeding material and/or mating interference.[2]
| |
 | |
| Names | |
|---|---|
| Preferred IUPAC name
(4S)-2-Methyl-6-methylideneocta-2,7-dien-4-ol | |
| Other names
(S)-(+)-Ipsdienol, 2-Methyl-6-methylene-2,7-octadiene-4-ol, Ipsdienol | |
| Identifiers | |
3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.128.974 |
| EC Number |
|
PubChem CID |
|
| UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
| Properties | |
| C10H16O | |
| Molar mass | 152.237 g·mol−1 |
| Appearance | Colorless |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H400 | |
| P273, P391, P501 | |
| Flash point | 87 °C (189 °F; 360 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Synthesis
The compound has been synthesized from D-mannitol.[3] Alternative syntheses were realized through the asymmetric isoprenylation of correspondent aldehyde (prenal)[4] and alcohol (prenol).[5] Chiral resolution of racemic precursor has been found[6][7] to provide both enantiomers of ipsdienol in high enantiomeric purity and in preparative scale.