PMID- 16157171
OWN - NLM
STAT- MEDLINE
DCOM- 20051114
LR  - 20161124
IS  - 0045-6535 (Print)
IS  - 0045-6535 (Linking)
VI  - 61
IP  - 1
DP  - 2005 Sep
TI  - Structure elucidation of hexabromocyclododecanes--a class of compounds with a 
      complex stereochemistry.
PG  - 65-73
AB  - Hexabromocyclododecanes (HBCDs) are high production volume chemicals (16700 t 
      worldwide in 2001) used as flame-retardants for plastics and textiles. HBCDs 
      exhibit typical properties of persistent organic pollutants (POPs). They are 
      highly lipophilic and accumulate in biota. Increasing environmental 
      concentrations of HBCDs, mostly reported as sum values, have been observed. As 
      such, HBCDs have to be considered as potential emerging POPs, but their 
      occurrence and environmental fate have not yet been addressed at the level of 
      individual HBCD stereoisomers. Considering the six stereogenic centers of HBCDs, 
      16 stereoisomers, six diastereomeric pairs of enantiomers as well as four meso 
      forms, can be deduced. Herein, we report spectroscopic and chromatographic data 
      for eight out of 16 possible HBCD stereoisomers, which were isolated from a 
      technical product. Six stereoisomers were identified as three pairs of 
      enantiomers ((+/-) alpha-, beta-, and gamma-HBCDs), differing in optical rotation 
      and chromatographic retention on a chiral phase. The crystal structures of these 
      pairs of enantiomers were determined. Another two of these eight HBCD 
      stereoisomers, not yet described in the literature, showed no optical rotation 
      and are tentatively assigned as meso forms (delta- and epsilon-HBCD). The given 
      spectroscopic and chromatographic information allows the unambiguous 
      identification of eight HBCD stereoisomers and the occurrence, fate, and 
      toxicology of these individual stereoisomers can now be studied.
FAU - Heeb, Norbert V
AU  - Heeb NV
AD  - Swiss Federal Institute for Materials Science and Technology (Empa), Laboratory 
      of Organic Chemistry, Uberlandstrasse 129, 8600 Dubendorf, Switzerland. 
      norbert.heeb@empa.ch
FAU - Schweizer, W Bernd
AU  - Schweizer WB
FAU - Kohler, Martin
AU  - Kohler M
FAU - Gerecke, Andreas C
AU  - Gerecke AC
LA  - eng
PT  - Journal Article
PL  - England
TA  - Chemosphere
JT  - Chemosphere
JID - 0320657
RN  - 0 (Environmental Pollutants)
RN  - 0 (Flame Retardants)
RN  - 0 (Hydrocarbons, Brominated)
RN  - 5I9835JO3M (hexabromocyclododecane)
SB  - IM
MH  - Chromatography
MH  - Crystallization
MH  - Environmental Pollutants
MH  - *Flame Retardants
MH  - Hydrocarbons, Brominated/*chemistry
MH  - Spectrum Analysis
MH  - Stereoisomerism
EDAT- 2005/09/15 09:00
MHDA- 2005/11/15 09:00
CRDT- 2005/09/15 09:00
PHST- 2004/07/19 00:00 [received]
PHST- 2005/02/11 00:00 [revised]
PHST- 2005/03/07 00:00 [accepted]
PHST- 2005/09/15 09:00 [pubmed]
PHST- 2005/11/15 09:00 [medline]
PHST- 2005/09/15 09:00 [entrez]
AID - S0045-6535(05)00422-4 [pii]
AID - 10.1016/j.chemosphere.2005.03.015 [doi]
PST - ppublish
SO  - Chemosphere. 2005 Sep;61(1):65-73. doi: 10.1016/j.chemosphere.2005.03.015.