Chemical Properties
(E,E)-2,4-Octadiene-1-ol has a mild, pleasant, fatty odor.
Uses
(2E,4E)-2,4-Octadien-1-ol is a useful intermediate used in the synthesis of sex pheromone component of sphingid moths and other sex attractants.
Definition
ChEBI: (2E,4E)-2,4-octadien-1-ol is an aliphatic alcohol.
Aroma threshold values
Aroma characteristics at 1%: fatty, chicken fat, with a creamy waxy nuance.
Taste threshold values
Taste characteristics at 1 to 5 ppm: fatty, oily and waxy with a broth savory chicken and beef note. Creamy
with a cucumber and melon nuance.
Synthesis
General method: Diisobutylaluminum hydride (DIBAL-H, 1M hexane solution) was added slowly and dropwise to an anhydrous dichloromethane (DCM) solution of the ester (cas:64713-73-1) at -78°C under argon protection. The reaction mixture was stirred continuously at -78 °C for 1.5 h before the reaction was quenched with 10% aqueous sodium hydroxide (NaOH) solution. Subsequently, the reaction system was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the organic and aqueous layers were separated and the aqueous layer was extracted three times with dichloromethane (DCM). All organic phases were combined, washed sequentially with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography to afford the target product 2,4-octadien-1-ol.
References
[1] Tetrahedron Letters, 2018, vol. 59, # 2, p. 103 - 107
