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Photooxidation of Cedrelone, a Tetranortriterpenoid from Toona ciliata ¶
Author(s) -
Gopalakrishnan Geetha,
Pradeep Singh N. D.,
Kasinath V.,
Malathi R.,
Rajan S. S.
Publication year - 2000
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1562/0031-8655(2000)0720464pocatf2.0.co2
Subject(s) - photooxygenation , dabco , rose bengal , singlet oxygen , photodissociation , chemistry , photochemistry , octane , oxygen , organic chemistry
Cedrelone, a tetranortriterpenoid on photolysis by UV light yields a true photooxidation product 3 [14 β,15β,22β,23β‐diepoxy‐6‐hydroxy‐1,5,20(22)‐meliatriene‐2,7,21‐trione] whose structure is well established by NMR studies and confirmed by X‐ray crystallography, along with product 4 [14 β,15β‐epoxy‐6,23‐dihydroxy‐1,5,20(22)‐meliatriene‐2,7,21‐trione]. Addition of rose bengal increases the rate of photooxidation whereas DABCO decreases rate of photolysis proving the involvement of singlet oxygen in the photooxygenation. Both the photoproducts exhibited antifeedant activity.