Pomarose has a powerful fruity rose odor with nuances of apples, plums and raisins, which is almost entirely due to the (2E,5Z)-stereoisomer, while its (2E,5E)-isomer is barely detectable for most people.
[2] Catalyzed by traces of acids, both isomers equilibrate however quickly upon standing in glass containers.
5,6,7-Trimethylocta-2,5-dien-4-one was suspected by Philip Kraft et al.[3] by investigation of the NMR spectra of an unknown trace component with damascone odor in a crude complex reaction product.
Pomarose was synthesized for structural curiosity and found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits with a low odor threshold of 0.5 ng/L air.
The synthesis comprised borontrifluoride-catalyzed addition of methyl isopropyl ketone to 1-ethoxyprop-1-yne, which afforded ethyl 2,3,4-trimethylpent-2-enoate, and then was transformed into the target molecule by Grignard reaction with propen-1-ylmagnesium bromide via in situ enolization.