Olean (pheromone)

Structural formula
( R ) -Olean and ( S ) -Olean
General
Surname	Olean
other names	( RS ) -1,7-dioxaspiro [5.5] undecane ( R ) -1,7-dioxaspiro [5.5] undecane ( S ) -1,7-dioxaspiro [5.5] undecane
Molecular formula	C 9 H 16 O 2
External identifiers / databases
CAS number 180-84-7 [( RS ) -Olean] 90839-15-9 [( R ) -Olean] 90839-16-0 [( S ) -Olean] EC number 205-870-7 ECHA InfoCard 100.005.338 PubChem 67437 Wikidata Q804105
properties
Molar mass	156.22 g mol −1
Physical state	liquid
density	1.020 g cm −3
boiling point	193 ° C
Refractive index	1.4640 (20 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

As a natural substance, Olean is an organic-chemical compound with a spiro structure and a full acetal .

Olive fruit fly ( Bactrocera oleae L.)

It is a sex pheromone of the olive fruit fly ( Bactrocera oleae L.) and occurs in two enantiomeric forms, the ( R ) -Olean and the ( S ) -Olean. The ( R ) -enantiomer acts on males, while the mirror-image ( S ) -enantiomer is ineffective on them. The female produces the racemate [1: 1 mixture of ( R ) -Olean and ( S ) -Olean], responds to both and thus also stimulates herself.

Olean can be produced in vitro by spiroacetalization of dihydropyran derivatives. An asymmetric synthesis is possible through the use of chiral Brønsted acids .

Individual evidence

1. ↑ ^{a b c d e} data sheet 1,7-Dioxaspiro [5.5] undecane, 98% from AlfaAesar, accessed on September 28, 2013 ( PDF )(JavaScript required) .
2. ↑ Bernd Schäfer: Natural substances in the chemical industry , spectrum Akademischer Verlag, 2007, pp. 522–524, ISBN 978-3-8274-1614-8 .
3. ^ Ilija Čorić, Benjamin List : Asymmetric spiroacetalization catalysed by confined Brønsted acids. In: Nature 483, 2012, pp. 315-319, doi : 10.1038 / nature10932 .