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Multistriatin

Multistriatin
Names
IUPAC name
5-ethyl-2,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane
Other names
(1S,2R,4S,5R)-5-ethyl-2,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C10H18O2/c1-4-10-8(3)5-7(2)9(12-10)6-11-10/h7-9H,4-6H2,1-3H3/t7-,8+,9-,10-/m1/s1
    Key: YMBRJMLOGNZRFY-UTINFBMNSA-N
  • CCC12C(CC(C(O1)CO2)C)C
Properties
C10H18O2
Molar mass 170.252 g·mol−1
Density 0.959 g/mL
Boiling point 207.1 °C (404.8 °F; 480.2 K)
Hazards
Flash point 74.9 °C (166.8 °F; 348.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Multistriatin is a pheromone of the elm bark beetle. It is a volatile compound released by a virgin female beetle when she has found a good source of food, such as an elm tree.[1]

Potential applications

Males beetles, which carry the fungus which causes Dutch elm disease, are attracted to the pheromone. Hence multistriatin could be used to trap beetles and so prevent the spread of the disease.[1][page needed][2]

Stereochemistry

The compound exists in several diastereomic forms, depending on the positions of the methyl groups.[3] Only the natural stereoisomer, α-multistriatin, attracts the elm bark beetles.

References

  1. ^ a b Warren, Stuart (1982). Organic synthesis : the disconnection approach.
  2. ^ Blight, Margaret M.; Fielding, N. J.; King, C. J.; Ottridge, A. P.; Wadhams, L. J.; Wenham, M. J. (1983). "Field response of the dutch elm disease vectors, Scolytus multistriatus (Marsham) andS. scolytus (F.) (Coleoptera: Scolytidae) to 4-methyl-3-heptanol baits containing ?-, ?-,?-, or ?-multistriatin". Journal of Chemical Ecology. 9 (1): 67–84. doi:10.1007/BF00987771. ISSN 0098-0331. PMID 24408620. Retrieved 21 October 2025.
  3. ^ Beck, Keith (1 September 1978). "Pheromone chemistry of the smaller European elm bark beetle". Journal of Chemical Education. 55 (9): 567. Bibcode:1978JChEd..55..567B. doi:10.1021/ed055p567.

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