The metabolism of the potent carcinogen estragole was investigated in humans after consumption of fennel tea by analyses of its metabolites in blood plasma and urine. Stable isotope dilution assays based on LC-MS/MS detection revealed that 1'-hydroxylation of estragole happened very fast as the concentration of conjugated 1'-hydroxyestragole in urine peaked after 1.5 h, whereas it was no longer detectable after 10 h. Besides the formation of less than 0.41% conjugated 1'-hydroxyestragole of the estragole dose administered, the further metabolite p-allylphenol was generated from estragole in a higher percentage (17%). Both metabolites were also detected in blood plasma in less than 0.75-2.5 h after consumption of fennel tea. In contrast to this, no estragole was present in these samples above its detection limit. From the results, it can be concluded that an excess of the major fennel odorant trans-anethole principally does not interfere with estragole metabolism, whereas influences on the quantitative composition of metabolites cannot be excluded. The presence of a sulfuric acid conjugate of estragole could not be confirmed, possibly due to its high reactivity and lability.

The flavor of fennel fruits and fennel tea was examined by aroma extract dilution analysis of the respective dichloromethane extracts. In both fennel fruits and tea, trans-anethole, anisaldehyde, and trans-4,5-epoxy-2(E)-decenal showed high flavor dilution (FD) factors followed by fenchone, 1,8-cineole, (R)-alpha-pinene, estragole, and beta-myrcene. On the basis of these results, the odorants showing higher FD factors were quantified in tea as well as in fruits, and odor activity values (OAV) in tea were calculated by dividing the concentration of the compound by its recognition threshold in water. The highest OAV was found for trans-anethole, followed by estragole, fenchone, 1,8-cineole, (R)-alpha-pinene, beta-myrcene, and anisaldehyde. From a comparison of the concentrations of odorants in fruits and tea, trans-anethole and estragole showed similar extraction rates of approximately 10-15%, whereas the extraction rates for (R)-alpha-pinene, beta-myrcene, and limonene were below 2%. In contrast to this, fenchone, camphor, linalool, and carvone showed higher extraction rates (26-50%), whereas the high apparent extraction rates of anisalcohol (393%) and vanilline (480%) were attributed to the formation from precursors. Sensory studies of aqueous models containing odorants in the amounts quantified in fennel teas revealed high similarity of the models with the tea and proved that all impact odorants had been identified in their correct concentrations. Further sensory experiments showed that estragole had no odor impact on the overall flavor of fennel tea, and, therefore, a reduction of estragole in fennel products would have no negative impact on their sensoric quality. In contrast to this, trans-anethole and fenchone were found to be character impact compounds of fennel.

Since estragole has been described as potent carcinogen and did not show any flavour impact on the odour of fennel, the flavour of anise and tarragon was examined by combinations of instrumental and sensory analyses. In anise fruits, trans-anethole, 2-isopropyl-3-methoxypyrazine, and anisaldehyde showed high flavour dilution (FD) factors, followed by those of eugenol, cis-anethole, estragole and linalool. Quantitation of the odorants showing higher FD factors in anise tea, and calculation of odour activity values (OAVs) by dividing the concentrations of the respective compound by its recognition threshold in water revealed the highest OAV for trans-anethole, followed by those of anisaldehyde and estragole. Still, an aroma impact of estragole next to trans-anethole could be neglected, due to former sensory studies of aqueous models of fennel tea. For tarragon, AEDA revealed the highest FD factors for eugenol, 7-methoxycoumarin, β β β β β -ionone, 2-isopropyl-3-methoxypyrazine, estragole and linalool. Of these, estragole and 7-methoxycoumarine were most abundant in tarragon leaves, showing contents of 2900 and 220 mg/kg, respectively. To calculate OAVs, the contents of potent odorants were divided by their odour threshold in starch or cellulose, as these were the main constituents of the leaves. In this way, β β β β β -ionone and eugenol showed the highest OAVs of 5862 and 2653, repectively, followed by estragole (OAV = = = = = 460), cis-1,5-octadiene-3-one (OAV = = = = = 140), vanilline (OAV = = = = = 139) and 2-isopropyl-3-methoxypyrazine (OAV = = = = = 130). Therefore, it was concluded that β β β β β -ionone and eugenol made the greatest contribution to the overall flavour of tarragon, whereas estragole and the other odorants were of minor importance.

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