88207-74-3Relevant academic research and scientific papers
Analytical and toxicity characterization of halo-hydroxyl-benzoquinones as stable halobenzoquinone disinfection byproducts in treated water
Wang, Wei,Qian, Yichao,Li, Jinhua,Moe, Birget,Huang, Rongfu,Zhang, Hongquan,Hrudey, Steve E.,Li, Xing-Fang
, p. 4982 - 4988 (2014/06/09)
Exposure to chlorination disinfection byproducts (DBPs) is potentially associated with an increased risk of bladder cancer. Four halobenzoquinones (HBQs) have been detected in treated drinking water and have shown potency in producing reactive oxygen species and inducing damage to cellular DNA and proteins. These HBQs are unstable in drinking water. The fate and behavior of these HBQs in drinking water distribution systems is unclear. Here we report the high-resolution mass spectrometry identification of the transformation products of HBQs as halo-hydroxyl-benzoquinones (OH-HBQs) in water under realistic conditions. To further examine the kinetics of transformation, we developed a solid-phase extraction with ultrahigh-performance liquid chromatography tandem mass spectrometry (SPE-UHPLC-MS/MS) method to determine both the HBQs and OH-HBQs. The method provides reproducible retention times (SD 50 of HBQs and OH-HBQs ranging from 15.9 to 72.9 μM. While HBQs are 2-fold more toxic than OH-HBQs, both HBQs and OH-HBQs are substantially more toxic than the regulated DBPs.
The Synthesis and Ring-contraction of Halogenated Hydroxyquinones; a New Synthesis of Cryptosporiopsin
Henderson, Graeme B.,Hill, Robert A.
, p. 2595 - 2599 (2007/10/02)
Syntheses of 2,6-dichloro- and 2,6-dibromo-3-hydroxy-5-alkyl-1,4-benzoquinones have been developed involving oxidation of trihalogenoresorcinol derivatives with Fremy's salt.The reactions of these quinones have been studied and their ring-contraction to cyclopentenoid structures on treatment with N-halogenosuccinimides is reported.This sequence of reactions has been used in an efficient synthesis of the fungal metabolite cryptosporiopsin.
