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)
|
|
ECHA InfoCard | 100.128.974 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
C10H16O | |
Molar mass | 152.237 g·mol−1 |
Appearance | Colorless |
Hazards | |
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).
|
(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]
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.
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)
|
|
ECHA InfoCard | 100.128.974 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
Properties | |
C10H16O | |
Molar mass | 152.237 g·mol−1 |
Appearance | Colorless |
Hazards | |
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).
|
(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]
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.