dioxin symposium 2010 san antonio, tx, us 光学異性体に関する研究発表

Dioxin symposium 2010San Antonio, TX, US

光学異性体に関する研究発表

第１０回　ｅ - シンポジウム　11.dec.2010

（大阪府環境農林水産総合研究所）

兵庫県環境研究センター松村千里

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component-MC7cis-chlordane

component-MC5trans-chlordane

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兵庫県でのこれまでの取り組んできた光学異性体が存在する POPs 化合物

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兵庫県でのこれまでの取り組んできた光学異性体が存在する POPs 化合物

PCBs ( 17 atropisomers )

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1332 THE SEA WATER CONCENTRATION AND ENANTIOMERIC FRACTION OF HCHs IN THE SEAS AROUND JAPAN

Suzuki M1, Tsurukawa M1, Abe S2, Matsumura C1, Nakano T1, Kunugi M3

1Hyogo Prefectural Institute of Environmental Sciences, Yukihira-cho 3-1-27, Suma-ku, Kobe, Hyogo　 654-0037, Japan,

2Hyogo Environmental Advancement Association, Yukihira-cho 3-1-31, Suma-ku, Kobe, Hyogo 654-0037, Japan,

3Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan

1332 THE SEA WATER CONCENTRATION AND ENANTIOMERIC FRACTION OF HCHs IN THE SEAS AROUND JAPAN

POPs 　（２題）1407 PERSISTENT ORGANIC POLLUTANTS IN THE ARCTIC AND CANADA’S NORTHERN CONTAMINANTS PROGRAM (NCP)1332 THE SEA WATER CONCENTRATION AND ENANTIOMERIC FRACTION 　 OF HCHs IN THE SEAS AROUND JAPAN

HBCDs 　（１２題）1244 IS HEXABROMOCYCLODODECANE (HBCD) A GLOBAL POP?THE NORWEGIAN PROPOSALS TO INCLUDE HBCD IN UN CONVENTIONS ON POPS1267 EMERGING HALOGENATED FLAME RETARDANTS IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN.1264 HEXABROMOCYCLODODECANE IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN: LEVELS AND ENANTIOMERIC PATTERNS.1091 AN OVERVIEW OF CONTAMINATION OF THE UK ENVIRONMENT WITH HBCD AND ITS DEGRADATION PRODUCTS1112 TIME COURSES OF HBCD LEVELS AND ENANTIOMERIC SIGNATURES IN HERRING GULL EGGS FROM THE GERMAN COAST1033 LEVELS OF HBCDs AND DEGRADATION PRODUCTS IN UK HUMAN MILK AND 　 RELATIONSHIP TO EXTERNAL EXPOSURE1195 HPLC BEHAVIOUR OF THE ISOMERS OF HEXABROMOCYCLODODECANE1193 FURTHER MINOR ISOMERS OF HEXABROMOCYCLODODECANE1113 HBCD ISOMERS: DEGRADATION RATES AND HYDROXYLATED PRODUCTS FROM MICROSOME INCUBATION EXPERIMENTS1416 INVESTIGATION OF HBCD METABOLISM IN MARINE MAMMALS FROM CANADA USING A HEPATIC MICROSOMAL IN VITRO BIOASSAY APPROACH AND COMPARISON WITH FIELD SAMPLES1409 IN VITRO METABOLISM OF HBCD ISOMERS BY RAT LIVER MICOSOMES1436 METABOLISM OF α- AND γ-HEXABROMOCYCLODODECANE AND ENANTIOSELECTIVE FRACTIONS OF α-, β-, γ-ISOMERS IN MICE

PFOS 　（２題）1460 ENANTIOSELECTIVE ANALYSIS OF A PFOS ISOMER: EVIDENCE FOR THE SOURCE CONTRIBUTION OF PRECURSORS TO AQUATIC ORGANISMS IN THE GREAT LAKES1417 Isomer and enantiomer enrichment of perfluorooctane sulfonate (PFOS) in rats exposed to a PFOS-precursor

Others 　（５題）1209 ATRAZINE AND METOLACHLOR IN ONTARIO SMALL LAKES and PRECIPITATION1068 STUDY OF DISTRIBUTION PATTERNS AND CONCENTRATIONS OF SHORT CHAIN CHLORINATED PARAFFINS IN FARM SOILS IRRIGATED WITH WASTEWATER1192 THE DRUG NAPROXEN AND ITS TRANSFORMATION PRODUCTS AS AN EXAMPLE FOR EMERGING ENVIRONMENTAL POLLUTANTS

光学異性体に関連する発表（ Chiral 、 Enantiomer ）

1244 IS HEXABROMOCYCLODODECANE (HBCD) A GLOBAL POP?THE NORWEGIAN PROPOSALS TO INCLUDE HBCD IN UN CONVENTIONS ON POPS

ConclusionHBCD has passed the POP screening criteria of the Stockholm Convention4 and has been recognized as a POP under UNECE LRTAP5. As a next step of the process under the Stockholm Convention, a Risk Profile has been elaborated providing more detailed information on the use, the environmental fate and toxic properties of HBCD. This will be discussed at the next POPRC Meeting in October 2010. Under UNECE LRTAP, the review process to identify risk management measures for HBCD and potential exemptions, taking into account the lack of alternatives and socio-economic implications, has recently been completed. HBCD is now pending a final decision by the Executive Body on risk management measures and a possible listing of HBCD as a POP. Considering all the information available, it may be concluded that the production and use of HBCD presents a risk to the environment and health such that global action is warranted.

ＨＢＣＤについて

1195 HPLC BEHAVIOUR OF THE ISOMERS OF HEXABROMOCYCLODODECANE

Figure 1: Structural configurations of 10 HBCD isomers (adapted from Heeb et al.)(Dotted lines indicate meso forms; only one enantiomer is shown for the remaining isomers).


Figure 2: X-ray structures of 10 HBCD diastereomers grouped into shape families: A1) Square, A2) Quadrilateral,B1) Irregular (slight distortion), and B2) Irregular (major distortion).

Figure 3: Elution profile of selected HBCD isomers (“shape family” indicated in brackets).


1267 　　 EMERGING HALOGENATED FLAME RETARDANTS IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN.

1416 　　 INVESTIGATION OF HBCD METABOLISM IN MARINE MAMMALS FROM CANADA USING A HEPATIC MICROSOMAL IN VITRO BIOASSAY APPROACH AND COMPARISON WITH FIELD SAMPLES

－ＨＢｒ－２（ＨＢ

ｒ）－３（ＨＢｒ）

1264 　　HEXABROMOCYCLODODECANE IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN: LEVELS AND ENANTIOMERIC PATTERNS.

1264 　　 HEXABROMOCYCLODODECANE IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN: LEVELS AND ENANTIOMERIC PATTERNS.

1091 　　 AN OVERVIEW OF CONTAMINATION OF THE UK ENVIRONMENT WITH HBCD AND ITS DEGRADATION PRODUCTS

1113 　　 HBCD ISOMERS: DEGRADATION RATES AND HYDROXYLATED PRODUCTS FROM MICROSOME INCUBATION EXPERIMENTS

Figure 1: Progress of EF-values from a-, β-, and γ- HBCD racemates during an incubation period of 50 min. Each data point represents the average of two incubations (double injection) with the corresponding standard deviation.


Figure 2: HPLC-MS/MS-chromatograms of (-)α-HBCD (A) and of the resulting monohydroxy-HBCDs (B), formed by microsomal incubation.


＋ OH 体

1112 　　 TIME COURSES OF HBCD LEVELS AND ENANTIOMERIC SIGNATURES IN HERRING GULL EGGS FROM THE GERMAN COAST

1436 　　 METABOLISM OF α- AND γ-HEXABROMOCYCLODODECANE AND ENANTIOSELECTIVE FRACTIONS OF α-, β-, γ-ISOMERS IN MICE

γ-[14C]HBCD dose was very rapid in that 　　 59% of dose was excreted in the feces and 28% in 　 urine within 4 days of dosing9

1033 　　 LEVELS OF HBCDs AND DEGRADATION PRODUCTS IN UK HUMAN MILK AND　 RELATIONSHIP TO EXTERNAL EXPOSURE

Table 1: Statistical summary of concentrations (ng g-1 lw) of target compounds and enantiomer fractions (EF) of HBCDs in the analysed human milk samples.

ΣHBCDs ranged from 1 to 22 ng g-1 lw

Figure 1: LC-MS/MS chromatograms of (a) PBCDs and (b) TBCDs in human milk.


Table 2: Exposure (ng kg-1 bw day-1) of a 1 month old infant to the target BFRs via breast milk.

Table 3: Estimated adult body burdens of HBCDs compared to observed levels in human milk.


1193 FURTHER MINOR ISOMERS OF HEXABROMO-CYCLODODECANE

Figure 1: Structural configurations of 10 HBCD isomers (adapted from Heeb et al.).(Dotted lines indicate meso forms; only one enantiomer is shown for the remaining isomers)

Figure 2: Elution order of 10 HBCD isomers on a Restek Ultra II C18 column (1.8 μm, 2.1 x 50 mm) using a MeOH/ACN/water gradient.

1193 FURTHER MINOR ISOMERS OF HEXABROMOCYCLODODECANE

Figure 3: Illustrating the influence of mobile phase composition on the elution order of the eta- and theta-HBCD isomers.

1193 FURTHER MINOR ISOMERS OF HEXABROMOCYCLODODECANE

1209 　　 ATRAZINE AND METOLACHLOR IN ONTARIO SMALL LAKES and PRECIPITATIONKurt-Karakus, PB1, Muir, DCG1, Bidleman, TF2, Teixeira, C1, Small, J1

1 Science and Technology Branch, Environment Canada, 867 Lakeshore Road, Burlington, L7R 4A6, ON, Canada, Tel: +1 905 319-6921, Fax:+1 905 336-64302 Center for Atmospheric Research Experiments, Environment Canada, 6248 Eighth Line, Egbert, L0L 1N0, ON, Canada, Tel: +1 705 458-3322, Fax: +1 705 458-3301

1192 THE DRUG NAPROXEN AND ITS TRANSFORMATION PRODUCTS AS AN EXAMPLE FOR EMERGING ENVIRONMENTAL POLLUTANTS

Hühnerfuss H1, Selke S1, Scheurell M1, Shah MR2, Nadeem S1,21University of Hamburg, Institute of Organic Chemistry, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany2HEJ Research Institute of Chemistry, University of Karachi, Karachi, Pakistan

1091 　　 AN OVERVIEW OF CONTAMINATION OF THE UK ENVIRONMENT WITH HBCD AND ITS DEGRADATION PRODUCTS

Harrad S1, Desborough J1, and Abdallah M A-E1,21Division of Environmental Health & Risk Management, School of Geography, Earth & Environmental Sciences, University of Birmingham, Birmingham, B15 2TT, UK2Department of Analytical Chemistry, Faculty of Pharmacy, Assiut University, 71526 Assiut, Egypt.

1267 　　 EMERGING HALOGENATED FLAME RETARDANTS IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN.

Guerra P.1, Pacepavicius G.2, Jiménez B.3, Muñoz-Arnanz J3., Blázquez E.3, Fernie K.4, Champoux L.5, Marvin C.2, Macinnis G.2, Eljarrat E.1, Barceló D. 1,6 and Alaee M.21Department of Environmental Chemistry, IDAEA-CSIC, Jordi Girona, 18-26. 08034 Barcelona, Spain; 2Water Science and Technology, Environment Canada, 867 Lakeshore Road, Burlington Ontario, Canada, L7R 4A6;3Department of Instrumental Analysis and Environmental Chemistry, Institute of Organic Chemistry, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain; 4Wildlife Toxicology and Disease, Environment Canada, 867 Lakeshore Road, Burlington, Ontario, Canada, L7R 4A6; 5Wildlife Toxicology and Disease, Environment Canada, 1141 Route de l'Église, Sainte-Foy, Quebec, Canada, G1V 4H5; 6Catalan Institute for Water Research (ICRA), Parc Científic i Tecnològic de la Universitat de Girona, Pic de Peguera 15, 17003 Girona, Spain.

1193 FURTHER MINOR ISOMERS OF HEXABROMOCYCLODODECANEMcCrindle R1,2, Riddell N1, Chittim B1, McAlees A11Wellington Laboratories Inc., 345 Southgate Drive, Guelph, Ontario, Canada; 2University of Guelph, Chemistry 　 Department, 50 Stone Road East, Guelph, Ontario, Canada

1460 ENANTIOSELECTIVE ANALYSIS OF A PFOS ISOMER: EVIDENCE FOR THE SOURCE CONTRIBUTION OF PRECURSORS TO AQUATIC ORGANISMS IN THE GREAT LAKES

Brian J. Asher1, Yuan Wang2, Amila De Silva3, Sean Backus3, Derek Muir3, Charles S. Wong1,4, Jonathan W. Martin1,21Department of Chemistry, University of Alberta, Edmonton, AB, Canada2Department of Laboratory Medicine and Pathology, University of Alberta, Edmonton, AB, Canada3Water Science and Technology Directorate, Environment Canada, Burlington, ON, Canada4Environmental Studies Program and Department of Chemistry, Richardson College for the Environment, University of Winnipeg, Winnipeg MB, Canada

1407 　　 PERSISTENT ORGANIC POLLUTANTS IN THE ARCTIC AND CANADA’S NORTHERN CONTAMINANTS PROGRAM (NCP)

Kurt-Karakus, PB1, Muir, DCG11 Science and Technology Branch, Environment Canada, 867 Lakeshore Road, Burlington, L7R 4A6, ON, Canada, Tel: +1 905 319-6921, Fax: +1 905 336-6430


Esslinger S, Becker R, Nehls IBAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Straße 11, 12489 Berlin, Germany

1416 　　 INVESTIGATION OF HBCD METABOLISM IN MARINE MAMMALS FROM CANADA USING A HEPATIC MICROSOMAL IN VITRO BIOASSAY APPROACH AND COMPARISON WITH FIELD SAMPLES

MacInnis GA1, Letcher RJ2, McKinney MA2, Tomy GT3, Lebeuf M3, Fång J4, Bergman Å4, Marvin CH11Environment Canada, Burlington, Ontario, Canada; 2Environment Canada, National Wildlife Research Centre, Carleton University, 1125 Colonel By Drive, Ottawa, Ontario, Canada; 3Fisheries and Oceans Canada, Winnipeg, Manitoba and Mont-Joli, Quebec, Canada; 4Department of Chemistry, University of Stockholm, Stockholm, Sweden

1332 THE SEA WATER CONCENTRATION AND ENANTIOMERIC FRACTION 　 OF HCHs IN THE SEAS AROUND JAPAN

Suzuki M1, Tsurukawa M1, Abe S2, Matsumura C1, Nakano T1, Kunugi M31Hyogo Prefectural Institute of Environmental Sciences, Yukihira-cho 3-1-27, Suma-ku, Kobe, Hyogo 　 654-0037, Japan, 2Hyogo Environmental Advancement Association, Yukihira-cho 3-1-31, Suma-ku, Kobe,Hyogo 654-0037, Japan, 3Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan

1264 　　 HEXABROMOCYCLODODECANE IN PEREGRINE FALCON (Falco peregrinus) EGGS FROM CANADA AND SPAIN: LEVELS AND ENANTIOMERIC PATTERNS.

Guerra P.1, Pacepavicius G.2, Jiménez B.3, Blázquez E.3, Fernie K.4, Champoux L.5, Marvin C.2, Macinnis G.2, Eljarrat E.1, Barceló D. 1,6 and Alaee M.21Department of Environmental Chemistry, IDAEA-CSIC, Jordi Girona, 18-26. 08034 Barcelona, Spain;2Water Science and Technology, Environment Canada, 867 Lakeshore Road, Burlington Ontario, Canada, L7R 4A6; 3Department of Instrumental Analysis and Environmental Chemistry, Institute of Organic Chemistry, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain; 4Wildlife Toxicology and Disease, Environment Canada, 867 Lakeshore Road, Burlington, Ontario, Canada, L7R 4A6; 5Wildlife Toxicology and Disease, Environment Canada, 1141 Route de l'Église, Sainte-Foy, Quebec, Canada, G1V 4H5; 6Catalan Institute for Water Research (ICRA), Parc Científic i Tecnològic de la Universitat de Girona, Pic de Peguera 15, 17003 Girona, Spain.

1112 　　 TIME COURSES OF HBCD LEVELS AND ENANTIOMERIC SIGNATURES IN HERRING GULL EGGS FROM THE GERMAN COAST

Esslinger Sa, Becker Ra, Jung Ca, Schröter-Kermani Cb, Nehls Iaa BAM Federal Institute for Materials Research and Testing, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germanyb UBA Federal Environment Agency, Corrensplatz 1, D-14195 Berlin, Germany

1409 IN VITRO METABOLISM OF HBCD ISOMERS BY RAT LIVER MICOSOMESRoosens Laurence1, Heather M. Stapleton2, Covaci Adrian1,31 - Toxicological Centre, Department of Pharmaceutical Sciences, Univ of Antwerp 2610 Wilrijk, Belgium2 - Duke University, Nicholas School of the Environment, Durham, NC3 - Laboratory for Ecophysiology, Biochemistry and Toxicology, Department of Biology, Univ of Antwerp 　 2020 Antwerp, Belgium


Harrad1 S, and Abdallah M A-E1,21Division of Environmental Health and Risk Management, School of Geography, Earth and Environmental 　 Sciences, University of Birmingham, Birmingham, B15 2TT, United Kingdom.2 Department of Analytical Chemistry, Faculty of Pharmacy, Assiut University, 71526 Assiut, Egypt.

1195 HPLC BEHAVIOUR OF THE ISOMERS OF HEXABROMOCYCLODODECANERiddell N1, McCrindle R1,2, Chittim B1, McAlees A11Wellington Laboratories Inc., 345 Southgate Drive, Guelph, Ontario, Canada; 2University of Guelph, Chemistry 　 Department, 50 Stone Road East, Guelph, Ontario, Canada

1244 IS HEXABROMOCYCLODODECANE (HBCD) A GLOBAL POP?THE NORWEGIAN PROPOSALS TO INCLUDE HBCD IN UN CONVENTIONS ON POPS

Becher G1, Tolfsen CC2, Säll L21 Division of Environmental Medicine, Norwegian Institute of Public Health, P.O.Box 4404 Nydalen, NO-0403 　 Oslo, Norway2 Section for Risk Assessment of Chemicals, Climate and Pollution Agency, PO Box 8100 Dep, NO-0032 Oslo, 　 Norway


Hakk H1, Huwe JK1, Szabo, DT2, Diliberto, JJ2, Birnbaum, LS31 USDA-ARS Biosciences Research Laboratory, 1605 Albrecht Boulevard, Fargo, ND 58102-2765 USA.2US-EPA. ORD, NHEERL, 109 TW Alexander Dr., Research Triangle Park, NC 27711 USA, 3NIEHS & NCI, P.O. Box 12233, Research Triangle Park, NC 27709

1417 Isomer and enantiomer enrichment of perfluorooctane sulfonate (PFOS) in rats exposed to a PFOS-precursor

Matthew S. Ross1, Yuan Wang3, Charles S. Wong1,2, Jonathan W. Martin1,31 University of Alberta, Department of Chemistry, Edmonton, Alberta T6G 2G2 Canada2 Environmental Studies Program and Department of Chemistry, Richardson College for the Environment, University of Winnipeg, Winnipeg, MB, R3B 2E9 Canada3 Division of Analytical and Environmental Toxicology, Department of Laboratory Medicine and Pathology, University of Alberta T6G 2G3

1068 STUDY OF DISTRIBUTION PATTERNS AND CONCENTRATIONS OF SHORT CHAIN CHLORINATED PARAFFINS IN FARM SOILS IRRIGATED WITH WASTEWATER

Lixi Zeng, Yawei Wang, Bo Yuan, Thanh Wang and Guibin Jiang State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, E-mail: [email protected]

ＰＦＯＳ及びその他の化合物について


Figure 1. Isomer compositions of an electrochemically fluorinated (ECF) FOSA standard and in the blood of rats exposed to ECF FOSA for 99 days.


Figure 2. Percent enrichment of branched PFOS and FOSA in the blood of rats after 99 days of exposure to ECF FOSA. Percentages indicate the approximate percent of enrichment of branched isomers.

Figure 3. Chromatograms demonstrating the separation of enantiomers of 1m-PFOS in standards (left, EF=0.512) and rat blood (right, EF=0.385).

1460 ENANTIOSELECTIVE ANALYSIS OF A PFOS ISOMER: EVIDENCE FOR THE SOURCE CONTRIBUTION OF PRECURSORS TO AQUATIC ORGANISMS IN THE GREAT LAKES

1192 THE DRUG NAPROXEN AND ITS TRANSFORMATION PRODUCTS AS AN EXAMPLE FOR EMERGING ENVIRONMENTAL POLLUTANTS

1068 STUDY OF DISTRIBUTION PATTERNS AND CONCENTRATIONS OF SHORT CHAIN CHLORINATED PARAFFINS IN FARM SOILS IRRIGATED WITH WASTEWATER

dioxin symposium 2010 san antonio, tx, us 光学異性体に関する研究発表

Documents

hexabromocyclododecane

cis mc

metabolism of hbcd isomers

trans cis trans mc

enantiomeric patterns

enantiomeric fraction

sea water concentration

enantiomeric fractionof