Safety evaluation of certain food additives - ipcs inchem

364 ALKOXY-SUBSTITUTED ALLYLBENZENES
Figure 2. Metabolism of safrole, myristicin and apiole
R'
R
Glu-S
Glc-O
R'
R
R'
R
HO
- O3SO
R'
R
O
O
O
O
OH
R"
O
R"
O
R"
O
sulfation
R"
O
reaction with
glutathione
R'
R
R'
R
R'
R
R'
R
HO
O
O
O
O
OH
R" R/R'/R"=H (safrole)
R=OCH3 R'/R"=H (myristicin)
O R=OCH3 R'=H R"=OCH3 (apiole)
hydrolysis
glucuronidation epoxidation
1'-hydroxylation
metabolites of O-demethylation, 1-hydroxylation and epoxidation and metabolites
subjected to both O-demethylation and epoxidation. Analysis of relative peak area
suggests that elemicin administered as such to rats produced significantly more
1-hydroxylation metabolite compared with safrole or myristicin at the same dose
level (Beyer et al., 2006).
O
R"
O
R"
O
OH
R"
O
Odemethylenation
R'
R
R'
R
R'
HO
HO
OH
OH
O
OH
R"
OH
R"
O-demethylenation
(myristicin, apiole)
ring hydroxylation
(safrole)
OH
R"
O