Estragole anise

Estragol, or methyl-chavicol, Cj(,H,.,0, is a constituent of tarragon, anise-bark, bay, fennel, and other essential oils. It is a strongly odorous liquid having the following characters —... 

Anethole can be crystallized from oils in which it occurs as a major component (star anise and sweet fennel oils), and estragole containing oils (e.g., basilicum oil). 

Aniseed (Anise) Pimpinella anisurn (Umbelliferae/ Apiaceae) ripe fruit 2-3 anethole (80-90) estragole (1-6) flavour, carminative, aromatherapy... 

Fennel oil, star anise and anise are natural sources of anethole, although synthetic substitutes are readily available. In many countries, the use of synthetic anethole in food products is illegal. Anethole can also be synthesized from estragole extracted from Pinus oil (Weiss, 2002). 

In summary, Foeniculum is stated to have three species, F. vulgare (fennel), F. azoricum Mill. (Florence fennel) and F. dulce (sweet fennel). Fennel is widely cultivated, both in its native habitat and elsewhere, for its edible, strongly flavoured leaves and seeds. The flavour is similar to, but milder than, that of anise and star anise. Anethole and fenchone are the major constituents of the solvent extract of seed phenols, free fatty acids, carbohydrates, proteins, vitamins and minerals have been reported in varying proportions. In the mature fruit, up to 95% of the essential oil is located in the fruit, greater amounts being found in the fully ripe fruit. Approximately 45 constituents have been determined from fennel seed oil, the main constituents being frans-anethole, fenchone, estragol (methyl chavicol), limonene, camphene, a-pinene and other monoterpenes, fenchyl alcohol and... 

Results of detailed GC-MS analysis of these two fractions are reported in Table 17.2 (volatile oil column and waxes column). Anise waxes were formed mainly by n-pentacosane (35.7%), n-heneicosane (25.8%), n-tricosane (10.3%), n-docosane (9.0%) and n-tetracosane (6.2%). Volatile oil contained 94.2% of anethole (cis and trnns). In the oil, estragole (1.4%), limonene (1.7%), linalool (0.3%), two terpineol isomers (0.3%) and linalyl acetate (0.3%) were also present. Caryophyllene (0.5%) and trans-bergamotene (0.7%) were the main compounds among sesquiterpenes. 

The GC-MS pattern of fruit volatile oil of star anise (7. vemm Hook) shows the presence of 25 components, which account for 99.9% of the total amount (Padmashree et al., 2007). The major components are trans-anethole (93.9%), estragole (1.05%) and limonene (1.05%) (Table 17.3). Fifteen components are identified from its acetone extract, accounting for 80.27% of the total amount. frans-Anethole (51.81%) is found as a major component, along with linoleic acid (11.6%), l-(4-methoxyphenyl)-prop-2-one (6.71%), foeniculin (5.29%) and palmitic acid (1.47%). 

The 5 C-values of natural anethole, mainly the trans-isomer, originating from anise oil, star anise oil or feimel oil [279], are between -26 and -33%o. This broad area of the 5 C-values may be due to the origin from different plant variants and local conditions of biosynthesis. Nature-identical anethole, which is prepared by isomerisation of estragole [279, 282], has 5 C-values with a range from -27.7 to -32.8%o. This is not very surprising, as estragol is often originating from the same natural source as anethole. The C-content of another nature-identical anethole (-30.7 to -32.1%o) may be due to its chemical synthesis from anisol and propionic acid derivatives or prope-nol, respectively [279]. 

Anethol fennel, star anise, estragol, syn. distinguish between different origins botanical origin and environm. influences [225, 283, 353]... 

Clausena anisata (Willd.) Benth. Semidried leaves of C. anisata from Kenya yielded an oil (1.5 %) which was rich in anethole (33). The plant is native to tropical Africa and has an anise-like odor. The oil from other conntries has a yield of 3.5 to 8% and contains anethole as the main component (75-90%) as well as anisaldehyde, anisketone, estragole and a-elemene. Extracts of the leaves and the essential oils are used in the bakery and confectionery industries (34)... 

The 4-methoxy pattern. The pivotal essential oil is 4-allylanisole, or methyl chavicol, or estragole (called esdragol in the old literature). This allyl compound is found in turpentine, anise, fennel, bay, tarragon, and basil. Its smell is light, and reminiscent of fennel. The propenyl analogue is called anethole, or anise camphor, and it is found in both anise and camphor. It is a... 

Gerhardt regarded essence of estragon and essence of anise as physical isomers with the formula What we now call estragole (b.p. 215°) and... 

Oxygenation in the position of cinnamic acid followed by methylation of the phenol and reduc tion of the acid to alcohol with subsequent elimination of the alcohol gives estragole (also known as methyl chavicol (52) and anethole (53)). Estragole is found in a variety of oils, mostly herb oils such as basil, tarragon, chervil, fennel, clary sage, anise, and rosemary. Anethole occurs in both the (E)- and (Z)-forms, the more thermodynamically stable (B)-isomer (shown in Figure 6.10) is... 

Pinene 2-8% pinene 1-4% myrcene 1-12% of-pheUandrene 1-25% Hmonene 8 30% fenchone 7-16% estragole 2-7% cw-anethole <0.5% rra/ii-anethole 15-40% anise ketone <0.05% tasmanian-type a -pinene 2-11% a-pheUandrene 1-8.5% hmonene 1 % fenchone 10-25% estragole 1.5-6% cis-anethole <0.5% trans-anethole 45-78% anisaldehyde <1% anisketone <0.05% /S-myrcene 0.1-1% hmonene 30-45% trans-dihydrocarvone max. 2.5% carvone 50-65% trans-casrveoh max. 2.5% trans-cinnamic aldehyde 70-90% cinnamyl acetate 1-6% eugenol <0.5% coumarin 1.5-4% rra s-2-methoxy-cinnamaldehyde 3-15%... 

Anise oil contains (rani-anethole (75-90%), estragole (methylchavicol) (1%), anise ketone ( -methoxyphenylacetone), and P-caryophyllene. Other compounds in minor concentrations include anisaldehyde, anisic acid (oxidation products of anethole), linalool, limonene, a-pinene, acetaldehyde, /)-cresol, creosol, hydroquinine, P-famesene, y-hima-chalene, neophytadiene, and ar-curcumene (karrer). ° ... 

Chinese star anise oil contains trans-anethole (80-90%) as its major component. Other constituents include estragole, 1,4-cineole,... 

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