Safrole

This substance is a typical member of a series of propenylbenzenes. These also include methyleugenol and estragole. The propenylbenzenes are natural and synthetic flavoring agents. Sassafras, containing high levels of safrole, used to be added to sarsaparilla root beer. Nowadays, safrole is still present in the diet as a (minor) component of various herbs and spices, e.g., cloves.

Safrole and related substances have been shown to be carcinogenic. Possible metabolic activation routes are 1'-hydroxylation, followed by sulfation, and epoxidation of the double bond in the propenyl group (Figure 9.5).

In the case of safrole, biotransformation data suggest that the 1'-hydroxy sulfate ester is the ultimate carcinogenic species capable of binding to DNA. Administration of 1'-hy-droxysafrole to sulfation-deficient mice resulted in a lower tumor incidence than administration of the metabolite to normal mice.

Safrole cyt. P - 450

1'- Hydroxysafrole sulfation

sulfation

Safrole cyt. P - 450

CH2 CH CH2

1'- Hydroxysafrole sulfate

Figure 9.5 Possible routes of metabolic activation of safrole.

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