Photochemical hydroperoxidation of terpenes I. Synthesis and characterization of α-pinene, β-pinene and limonene hydroperoxides

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.…”

Solid Materials as Sources for Synthetically Useful Singlet Oxygen

“…[15] However, RB on polystyrene is clearly a more stable sensitizer than RB in cellulose acetate. [16] While leaching of RB from the latter matrix by the solvent is negligible, photobleaching is very fast, as was demonstrated in the 1 O 2 -mediated oxidation of butyl sulfide to the sulfoxide.…”

Analysis of Car-3-en-5-hydroperoxide

“…Looking at the abundant olefinic structures of oligoisoprenoids in essential oils, photo- [1,2] and autoxidation reactions [3,4] to peroxides must be expected. However, steam distillation followed by high resolution gas chromatography is still common in essential oil analysis, and both steam and the hot injector surface inevitably degrade any primary terpene (hydro) peroxides present in the sample.…”

“…Occasionally, endo-and hydroperoxides were isolated from solvent extracts of medical plants [6]. Indirect evidence for a secondary formation of peroxo-structures is provided by the frequently observed antimicrobial properties of essential oils, which are increasing during aging [1].…”

“…Isolation and separation of peroxides was usually carried out using liquid chromatography on silica phases [9], followed by mass spectrometry [10]. Different ionization methods were applied to analyze hydroperoxides of (-)-limonene, linalool, (-)-β-pinene, (+) and (-)-α-pinene [1,2,7,8]. The hydroperoxidation of (+)-car-3-ene was suggested, but no attempts were made to isolate and structurally characterize the product(s) [4].…”