2,3-二溴丙基-2,4,6-三溴苯基醚（DPTE）的合成和表征以及在海豹脂和大脑中发现的结构相关化合物。,Environmental Science & Technology

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2,3-二溴丙基-2,4,6-三溴苯基醚（DPTE）的合成和表征以及在海豹脂和大脑中发现的结构相关化合物。
Environmental Science & Technology ( IF 10.8 ) Pub Date : 2007-04-03 , DOI: 10.1021/es062383s
Roland von der Recke ₁ , Walter Vetter

Affiliation

之前被描述为来自巴伦支海的带帽海豹（Cystophora cristata）的脂提取物中未知的未知化合物UBC-1被鉴定为2,3-二溴丙基-2,4,6-三溴苯基醚（DPTE）。DPTE是溴化阻燃剂（BFR）Bromkal 73-5 PE的主要成分，是通过将溴与烯丙基2,4,6-三溴苯基醚（ATE）亲电加成而合成的。通过合成的外消旋体的气相色谱对映体分离证明了DPTE的手性。根据GC / ECNI-MS离子色谱图（m / z79和81），DPTE是巴伦支海和格陵兰海的带帽海豹和竖琴海豹（Phoca groenlandica）的脂和脑样本中的主要有机溴化合物。脂肪和脑中DPTE的浓度分别高达470和340微克/千克湿重。紧接DPTE的是天然二溴三氯单萜（MHC-1），人为BDE 47和BDE 99以及ATE，3,5-dibromo-2-（2'，4'-dibromo）-苯氧基苯甲醚（6- MeO-BDE 47），2-溴烯丙基-2,4,6-三溴苯醚（BATE）和4,6-二溴-2-（2'，4'-二溴）-苯氧基苯甲醚（2'-MeO-BDE 68 ）的相关性在降低。通过E2消除从DPTE合成了在环境样品中首次检测到的BATE。在竖琴海豹的大脑样本中，DPTE，ATE和BATE是最丰富的有机溴化合物，而实际上不存在多溴联苯醚（PBDEs）和MHC-1。这表明DPTE，ATE和BATE能够穿透血脑屏障。ATE和BATE在受DPTE污染的样品中通常同时存在，支持以下假设：这些化合物是DPTE的生物转化产物。具有超还原性类胡萝卜素的DPTE的厌氧转化研究导致了ATE的形成。此外，检测到2,4,6-三溴苯酚（TBP）和其他两个未知的次要转化产物。

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Synthesis and characterization of 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE) and structurally related compounds evidenced in seal blubber and brain.

The unknown compound UBC-1 previously described as the major organobromine contamination in the blubber extract of a hooded seal (Cystophora cristata) from the Barents Sea was identified as 2,3-dibromopropyl-2,4,6-tribromophenyl ether (DPTE). DPTE, which is the main component of the brominated flame retardant (BFR) Bromkal 73-5 PE, was synthesized by electrophilic addition of bromine to allyl-2,4,6-tribromophenyl ether (ATE). The chirality of DPTE was proven by gas chromatographic enantioseparation of the synthesized racemate. On the basis of GC/ECNI-MS ion chromatograms (m/z79 and 81), DPTE was the dominating organobromine compound in blubber and brain samples of hooded seals and harp seals (Phoca groenlandica) from the Barents and Greenland Seas. The concentrations of DPTE in blubber and brain were up to 470 and 340 microg/kg wet weight. Next to DPTE, the natural dibromo-trichloromonoterpene (MHC-1), the anthropogenic BDE 47 and BDE 99, as well as ATE, 3,5-dibromo-2-(2',4'-dibromo)-phenoxyanisole (6-MeO-BDE 47), 2-bromoallyl-2,4,6-tribromophenyl ether (BATE), and 4,6-dibromo-2-(2',4'-dibromo)-phenoxyanisole (2'-MeO-BDE 68) were present with decreasing relevance. BATE, which was detected for the first time in environmental samples, was synthesized from DPTE by E2 elimination. In brain samples of the harp seals, DPTE, ATE, and BATE were the most abundant organobromine compounds, whereas polybrominated diphenyl ethers (PBDEs) and MHC-1 were virtually absent. This indicated that DPTE, ATE, and BATE were able to penetrate the blood-brain barrier. The general co-occurrence of ATE and BATE in samples contaminated with DPTE support the hypothesis that these compounds are biotransformation products of DPTE. Anaerobic transformation studies of DPTE with super-reduced corrinoids resulted in the formation of ATE. Furthermore, 2,4,6-tribromophenol (TBP) and two other unknown minor transformation products were detected.

更新日期：2019-11-01

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