Investigation of singlet oxygen reactivity towards propofol

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Abstract
The reaction between the anaesthetic agent 2,6-diisopropylphenol (propofol, PPF) and singlet oxygen (1O2) has been investigated in aqueous solution by means of HPLC, GC, absorption spectroscopy and laser flash photolysis with infrared luminescence detection. The rate constants for the physical and chemical quenching of 1O2 by PPF (kPPF) are found to be 2.66 × 105 M−1 s−1 and ∼3.2 × 106 M−1 s−1 in CD3OD and D2O–CD3OD (75:25 v/v), respectively. The reaction of propofol with singlet oxygen produced by light irradiation of Rose Bengal leads essentially to two reaction products, 2,6-diisopropyl-p-benzoquinone and 3,5,3′,5′-tetraisopropyl-(4,4′)-diphenoquinone that are unambiguously identified from comparison with authentic samples.