I have sent a sample of mint essential oil for GC/MS analysis. in the analysis there is a component with this formula:
2-Cyclohexen-1-one, 2-methyl-5-(1-methylethyl)-, (S)-
Do you please have an I dea what is the name of this component? I mean menthol, carvone etc?
In general, Mentha spicata known to synthesize C6-oxygenated monoterpenoids i.e., carvone. Since, the compound name mentioned above possessed ketonic moiety/ functional group , the possibility is more for carvone. Based on nomenclature, 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)- is also correct.
Further, i suggest the following name
1-Methyl-4-(1-methylethenyl)-1-cyclohexen-6-one
or simply carvone.
Since, no chiral differentiation study was carried out. Therefore, omit the term (S)-. Further, menthol is a characteristic feature of other commercially important mint crops like M. arvensis and M. piperita essential oils.
You may visit the link shown below for detail information:
http://www.sciencedirect.com/science/article/pii/S157002321530101X
doi:10.1016/j.jchromb.2015.07.034
Best of Luck
Sorry to correct the colleague, but there was a misunderstanding in the chemical names by one of you. If the compound name came out as "2-Cyclohexen-1-one, 2-methyl-5-(1-methylethyl)-, (S)-" as type it corresponds to a compound with molecular formula C10H16O, M= 152, for the compound named "Cavotanacetone". On the other hand, the name the other colleague understood was "2-Cyclohexen-1-one, 2-methyl-5-(1-methylethenyl)- ", that indeed is the other name for carvone, but mind that there is a difference in the names that I marked in bold. This second name will correspond to a compound with molecular formula C10H14O, with M=150 (carvone). You can check in you MS analysis the correct molecular weight and the corresponding retention indexes for both compounds RI=1239 for carvone and RI=1244 for carvotanacetone.
Thanks Dr. Moreno for adding another dimension to this discussion. I fully agree with you for possibility of cavotanacetone if the compound does not have an additional double bond as in the case of carvone (in isopropyl position). Since, listed RIs are very close. Hence, two amu difference in mw shall be enough to find the answer. I doubt if the name is merely an outcome of library search. As far as my knowledge is concerned, M. spicata does not synthesize cavotanacetone. I feel the molecular wt of the peak (mass spectrum) can give a better clarity. Interestingly, one cannot overlook the term carvo- (common name) due to the structural similarly in both. Moreover, the correct is carvotanacetone.
Thanks
Thanks Dr. Monero and Dr. Chanotiya for such valuable information.
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