A major compound of technical toxaphene (CTT) was
isolated from seal blubber. The structure of the
octachlorobornane was elucidated by use of 1H-NMR and
mass
spectrometry. The isolate had the structure
2-endo,3-exo,
5-endo,6-exo,8,8,9,10-octachlorobornane
(B8-1412). By
comparison of the 1H-NMR data of B8-1412 and
2-endo,
3-exo,5-endo,6-exo,8b,8c,9c,10a,10c-nonachloro-
bornane (B9-1679) as well as semiempirical AM1
calculations,
the optimal conformation of the substituents at C8, C9,
and C10 was predicted to be
2-endo,3-exo,5-endo,6-exo,
8b,8c,9c,10c-octachlorobornane. B8-1412 was also
identified
in the technical mixture Melipax. The enantiomers of
B8-1412 were partly resolved by enantioselective gas
chromatography with a chiral stationary phase.
Furthermore,
it was shown that B8-1412 is a major CTT in adipose tissue
of penguin and seal. We also proved that another
major
CTT in biota is identical with the commercially available
2-exo,5,5,8c,9b,9c,10a,10b-octachlorobornane
(B8-2229), as
it was suggested earlier on the basis of its retention
time
on capillary columns with different polarity.
