ethylsulfide applying two cytochrome P-450 isoenzymes purified from
phenobarbital-induced rat liver, both of which generated 4-tolyl ethyl sulfoxide
(Fig. 1.4), exhibiting predominantly the (S)-(À)-configuration. An example for a
stereogenic phosphorus centre is represented by ruelene, that is, (R,S)-4-tertbutyl-2chlorophenylmethyl-N-methyl phosphoramidate.
Table 1.1 Chiral environmental pollutants, which are discussed in the present monograph, with
one or more stereogenic centres linked with four different substituents; examples for central
asymmetry
Chiral environmental pollutant
Chapters of the present
monograph
Dichlorprop (DCPP; i.e. (R,S)-2-(2,4-dichlorphenoxy)propionic acid) 8.1; 8.2; 10.5
Methyl dichlorprop (i.e. methyl-(R,S)-2-(2,4-dichlorphenoxy)
propionate)
8.1; 8.2
MCPP (i.e. 2-(4-chloro-2-methyl-phenoxy)propionic acid)
8.1
Ruelene, i.e. (R,S)-4-tertbutyl-2-chlorophenylmethyl-N-methyl
phosphoramidate (stereogenic phosphorus-Centre)
8.2
o,p
0 -DDT
5.1; 5.4; 8.1; 8.2; 8.3;
9.3; 10.2
o,p
0 -DDD
5.4; 8.1; 8.2; 9.3; 9.4;
10.1;
Chlordanes (cis-, trans-, other congeners)
5.4; 8.1; 8.2; 9.3; 10.2
Oxychlordane
5.4; 8.1; 8.2; 9.3; 10.2
Chlordene and metabolites
8.2
Photochlordene
8.2
Heptachlor
5.1; 8.1; 8.2; 9.3, 10.2
Heptachlor exoepoxide
5.1; 8.1; 8.2; 9.3, 10.2
Bromocyclen
8.1; 8.2
Toxaphene
®
8.2; 10.2
HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta
[g]-2-benzopyrane; Galaxolide
®
; two stereogenic centres)
1.6; 8.2
Galaxolidone (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8hexamethylcyclopenta[g]-2-benzopyrane-1-one metabolite of
Galaxolide
®
; two stereogenic centres)
8.2
AHTN (1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2naphthalenyl)-ethanone; Tonalide
®
)
8.2
ATII (1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methyl-ethyl)-1Hinden-5-yl]-ethanone; Traseolide
®
; two stereogenic centres)
8.2
AHDI (1-(2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl)ethanone; Phantolide
®
)
8.2
Thalidomide (Contergan
®
)
9.1
Naloxone (three stereogenic carbon centres, one nitrogen Centre)
1.6
Tetrodotoxin
10.2
Saxitoxin
10.2
Anatoxin-a and homoanatoxin-a
10.2
8
1 Introduction
phenobarbital-induced rat liver, both of which generated 4-tolyl ethyl sulfoxide
(Fig. 1.4), exhibiting predominantly the (S)-(À)-configuration. An example for a
stereogenic phosphorus centre is represented by ruelene, that is, (R,S)-4-tertbutyl-2chlorophenylmethyl-N-methyl phosphoramidate.
Table 1.1 Chiral environmental pollutants, which are discussed in the present monograph, with
one or more stereogenic centres linked with four different substituents; examples for central
asymmetry
Chiral environmental pollutant
Chapters of the present
monograph
Dichlorprop (DCPP; i.e. (R,S)-2-(2,4-dichlorphenoxy)propionic acid) 8.1; 8.2; 10.5
Methyl dichlorprop (i.e. methyl-(R,S)-2-(2,4-dichlorphenoxy)
propionate)
8.1; 8.2
MCPP (i.e. 2-(4-chloro-2-methyl-phenoxy)propionic acid)
8.1
Ruelene, i.e. (R,S)-4-tertbutyl-2-chlorophenylmethyl-N-methyl
phosphoramidate (stereogenic phosphorus-Centre)
8.2
o,p
0 -DDT
5.1; 5.4; 8.1; 8.2; 8.3;
9.3; 10.2
o,p
0 -DDD
5.4; 8.1; 8.2; 9.3; 9.4;
10.1;
Chlordanes (cis-, trans-, other congeners)
5.4; 8.1; 8.2; 9.3; 10.2
Oxychlordane
5.4; 8.1; 8.2; 9.3; 10.2
Chlordene and metabolites
8.2
Photochlordene
8.2
Heptachlor
5.1; 8.1; 8.2; 9.3, 10.2
Heptachlor exoepoxide
5.1; 8.1; 8.2; 9.3, 10.2
Bromocyclen
8.1; 8.2
Toxaphene
®
8.2; 10.2
HHCB (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethyl-cyclopenta
[g]-2-benzopyrane; Galaxolide
®
; two stereogenic centres)
1.6; 8.2
Galaxolidone (1,3,4,6,7,8-hexahydro-4,6,6,7,8,8hexamethylcyclopenta[g]-2-benzopyrane-1-one metabolite of
Galaxolide
®
; two stereogenic centres)
8.2
AHTN (1-(5,6,7,8-tetrahydro-3,5,5,6,8,8-hexamethyl-2naphthalenyl)-ethanone; Tonalide
®
)
8.2
ATII (1-[2,3-dihydro-1,1,2,6-tetramethyl-3-(1-methyl-ethyl)-1Hinden-5-yl]-ethanone; Traseolide
®
; two stereogenic centres)
8.2
AHDI (1-(2,3-dihydro-1,1,2,3,3,6-hexamethyl-1H-inden-5-yl)ethanone; Phantolide
®
)
8.2
Thalidomide (Contergan
®
)
9.1
Naloxone (three stereogenic carbon centres, one nitrogen Centre)
1.6
Tetrodotoxin
10.2
Saxitoxin
10.2
Anatoxin-a and homoanatoxin-a
10.2
8
1 Introduction