Toxicity anethole

N.A. Estragol, anethole, dictamnin." This herb is toxic. Stimulates the muscles of the uterus, antispasmodic. 

Anethole is found in essential oils of anise and fennel, ft exists as cis and fra ns forms, with the cis being more toxic. (Recall that cis and frans forms of a molecule are isomers that differ in the arrangement of groups attached to double bonds see Ch. 2.)... 

The essential oil of fennel seeds from the USA, Germany and India was separated by steam distillation or selective C02-extraction. Both procedures gave similar essential oil yields of about 6% for the German and US material (bitter fennel) and 2% for the Indian material (sweet fennel). Under stressing conditions the main component, trans-anethol (sweet taste), can be isomerised into c/ -anethol (not sweet), or can be oxidised to anisaldehyde, as shown in Fig. 2.30. Both compounds can simply be detected by HPLC-UV as trace components in fennel oils. Their content should be as low as possible, since fennel oil with more than 2% of anisaldehyde is considered to be spoiled by oxidation and cA-anethol has a 15-times higher toxicity compared to the natural trans-isomtv. 

Composition The ISO standard for aniseed [15] specifies the E-anethole content as 87-94%. Z-anethole (the more toxic isomer and transformation product of E-anethole when exposed to UV light [16]) is limited to 0.4%. The typical constituent of aniseed oil, pseudoisoeugenyl 2-methylbutyrate ]17] can occur up to 2%. Eor further confirmation of its natural origin by chirality GC, see ] 18]. Further constituents are methyl chavicol (up to 3%), gamma-himachalene (up to 5%), anisic aldehyde (up to 1.4%) and e.g. small amounts of monoterpenes. 

Anethole, anisaldehyde, and myristicin (in aniseed), along with z/-carvone (present in P. anisum plant), have shown mild insecticidal properties. In houseflies, the major (56% by weight) active insecticide in the oil from anise tops was shown to be frans-anethole. Anisaldehyde and anethole increased the toxicity to houseflies when applied at the same as various common insecticides. Anethole also inhibits growth of mycotoxin-producing Aspergillus species in culture. ... 

Steam distillation of Mexican avocado leaves yielded 3.1% of an essential oil consisting of 95% estragole (see sweet basil for toxicity) and 5% anethole. The fruit peel contains /-epicatechin. " ... 

Anethole is reported to have allergenic, weakly insecticidal, and toxic properties (see anise). It also stimulates secretions of the... 

Synthetic polymers such as poly(vinyl sulfate) and poly (anethole sulfonate) are highly charged heparin-like polyanions that also exhibit anticoagulant activity.23 However, these agents are not used in vivo as they are resistant to metabolism and thus remain in the body for extended periods resulting in toxic side effects. 23... 

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