(S)-Ipsdienol

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(S)-Ipsdienol
S-Ipsdienol.svg
Ipsdienol molecule
Names
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
Properties
C10H16O
Molar mass 152.24 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).
Infobox references

(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, facilitiating reductions in competition for breeding material and/or mating interference.[2]

Synthesis[edit]

The compound has been synthesized from D-mannitol.[3]

References[edit]

  1. ^ Silverstein, Robert M; Rodin, J. Otto; Wood, David L. (October 1966). "Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine". Science. 154 (3748): 509–510. Bibcode:1966Sci...154..509S. doi:10.1126/science.154.3748.509 (inactive 2017-08-26). JSTOR 1720044. 
  2. ^ Miller, Daniel R.; Borden, John H.; King, G. G. S.; Slessor, Keith N. (1 August 1991). "Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae)". Journal of Chemical Ecology. 17 (8): 1517–1527. doi:10.1007/BF00984685. PMID 24257877. 
  3. ^ Hanessian, Stephen (1983). Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. p. 63. ISBN 978-0-08-029247-2.