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
CAS Number	59014-03-8;
3D model (JSmol)	Interactive image;
PubChem CID	13199930;
UNII	CCJ8A99MHA;
	SMILES CCC12C(CC(C(O1)CO2)C)C;
Properties
Chemical formula	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). Infobox references

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]

Stereochemistry

The compound exists in several diastereomic forms, depending on the positions of the methyl groups.^[2] Only the natural stereoisomer, α-multistriatin, attracts the elm bark beetles.

References

^ ^a ^b Warren, Stuart (1982). Organic synthesis : the disconnection approach.
^ Beck, Keith (1 September 1978). "Pheromone chemistry of the smaller European elm bark beetle". Journal of Chemical Education. 55 (9): 567. doi:10.1021/ed055p567.

[disconnection_approach-1] Warren, Stuart (1982). Organic synthesis : the disconnection approach.

[2] Beck, Keith (1 September 1978). "Pheromone chemistry of the smaller European elm bark beetle". Journal of Chemical Education. 55 (9): 567. doi:10.1021/ed055p567.

[1]

[2]