Chemical oxidation of citronellol in the ‘dark’ and ‘light’ conditions

Siedlecka, Joanna; Łozińska, Iwona; Zawadzka, Anna; Czarnocki, Zbigniew; Kaczorowska, Ewa; Kania, Magdalena; Danikiewicz, Witold; Świeżewska, Ewa

doi:10.1016/j.chemphyslip.2011.05.120

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“…Of the tested isoprenoids, solanesol has the highest melting point, i.e., 35 °C, while short-chain isoprenoid alcohols have boiling points above 220 °C, even though as constituents of essential oils they are considered to be relatively volatile [33]. Short-chain prenols such as nerol, geraniol or citronellol undergo oxidation initiated by singlet oxygen formed from hydrogen peroxide in the presence of catalytic amounts of manganese (III) porphyrin complexes [34] or molybdate ions [35] as well as by singlet oxygen generated by halogen lamp irradiation in the presence of a photosensitizer (porphyrin) [36] with the formation of hydroperoxides, diols, epoxides, epoxy-diols and epoxy-ketones. These products can also be formed during autoxidation and thermo-oxidation.…”

Section: Discussionmentioning

confidence: 99%

Double Bond Stereochemistry Influences the Susceptibility of Short‐Chain Isoprenoids and Polyprenols to Decomposition by Thermo‐Oxidation

Molińska

Klimczak

Komaszyło

et al. 2015

Lipids

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Isoprenoid alcohols are common constituents of living cells. They are usually assigned a role in the adaptation of the cell to environmental stimuli, and this process might give rise to their oxidation by reactive oxygen species. Moreover, cellular isoprenoids may also undergo various chemical modifications resulting from the physico-chemical treatment of the tissues, e.g., heating during food processing. Susceptibility of isoprenoid alcohols to heat treatment has not been studied in detail so far. In this study, isoprenoid alcohols differing in the number of isoprene units and geometry of the double bonds, β-citronellol, geraniol, nerol, farnesol, solanesol and Pren-9, were subjected to thermo-oxidation at 80 °C. Thermo-oxidation resulted in the decomposition of the tested short-chain isoprenoids as well as medium-chain polyprenols with simultaneous formation of oxidized derivatives, such as hydroperoxides, monoepoxides, diepoxides and aldehydes, and possible formation of oligomeric derivatives. Oxidation products were monitored by GC-FID, GC-MS, ESI-MS and spectrophotometric methods. Interestingly, nerol, a short-chain isoprenoid with a double bond in the cis (Z) configuration, was more oxidatively stable than its trans (E) isomer, geraniol. However, the opposite effect was observed for medium-chain polyprenols, since Pren-9 (di-trans-poly-cis-prenol) was more susceptible to thermo-oxidation than its all-trans isomer, solanesol. Taken together, these results experimentally confirm that both short- and long-chain polyisoprenoid alcohols are prone to thermo-oxidation.

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Section: Discussionmentioning

confidence: 99%