HRGC separation of hydroperoxides formed during the photosensitized oxidation of (R)—(+)‐Limonene

Abstract

Summary(R) -(+)-Limonene was photooxidized in the presence of Rose Bengal as catalyst. After TLC isolation, the hydroperoxides formed were separated directly by HRGC and analyzed by MS (El; Cl). Each hydroperoxide isomer was then isolated by HPLC for structure determination which after reduction of the HOO group with sodium borohydride was performed by 'H-NMR and Six hydroperoxide isomers formed by oxidation of the endocyclic double bond were identified. The compounds eluted from the HRGC column in the following order (proportions are given in brackets) I (40

Multidimensional analysis of cannabis volatile constituents: Identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L.

“…allylic hydroperoxides (Fig. 9) [43,44]. Since hydroperoxides are generally not stable-in-time, they will generate the corresponding alcohols by reductive loss of an oxygen atom.…”

“…These compounds, somewhat rare in nature, were identified on the basis of their mass spectra, in all respects comparable with those of the literature (Fig. S1; see supporting information) [11,43].…”

A Different Aging Model for Orange Oil: Deterioration Products

“…On the other hand, efforts have also been put forth to elucidate the mechanisms of the various photoreactions, which also often produce off-flavors (10)(11)(12)(13). The formation of hydroperoxides from (R)-limonene was described in detail by Grosch et al (10).…”

“…The different fractions were eluted with n-pentane and n-pentane/diethyl ether (2,6,8,10,14,20,50 and 100%) as the mobile phase with increasing polarity. After the final removal of solvent, the collected fractions were submitted to GUMS and monitored together with n-alkanes on GC .…”

Are contact allergens stable in patch test preparations? Investigation of the degradation of d‐limonene hydroperoxides in petrolatum

“…Identification of individual compounds was performed by using GC-MS (gas chromatographymass spectrometry) and reference compounds, as described previously (7,8). 4 main hydroperoxides were formed upon autoxidation of d-limonene, i.e.…”