Anethole fennel

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

ISO standard 3475 shows character and data for that oil. This oil often is produced not only from the fruits but also from the whole aerial part. Values of cis- and tran -anethole are then reduced in smaller amount. Adulteration with star anise oil can be easily detected. Anise fruit oil does not contain any foeniculin, but star anise oil contains up to 3% (ISO 11016). On the other hand pseudo-isoeugenol-2-methylbutyrate is a component of anise fruit oil (0.3%-2%, ISO 3475) and does not appear in star anise oil. The midratio of cA-anethole to frani -anethole in anise seed oil in relation to star anise oil is 0.3% 0.6%. Synthetic anethole, fennel terpene limonene (80°), and terpineol were used for blending. 

ANETHOLE Up to 90+% in anise seed oil, 70+% in fennel and star anise oils, and in varying amounts in betel leaf, dill seed, carrot seed and coriander oils. 

Other synthetics with cost advantages and large volume productions are L-carvone [6485-40-17, the primary component in natural spearmint essence D-carvone [2244-16-8], the primary component in natural diU and caraway anethol [4180-23-8], in place of anise and fennel spices and smaller amounts of thymol [89-83-8] replacing thyme and disulfide synthetics for onion and gadic. AH of these synthetics must be labeled as artificial which may limit their use among consumers. 

The sweet Uoman fennel, as it is termed, ns anethol and little or no fenohone. It has the folhn... 

Macedonian fennel yields a verv similar oil. Wild bitter fennel, growing in France, Spain, and Algeria, yields an oil of specidc gravity 0-90.5 to 0 92.5 and an optical rotation up to 50. ft is practically free from anethol. Indian fennel oil has a specific gravity "970 and au optical rotation + 21°. 

Wild bitter fennel oil differs considerably from the ahcve-described oils. Its specific gnivily varies from 0 L05 to 0 925, aud optical rotation + 40° to + 66 - -Anethol is present onlv in traces, but a [air amount of phellandrene is present. Tardy isolated from this oil a crystalline compound melting at 213", which is possibly di-para-1 Bull. Sat. Chin., xvil, 660. 

Anisic aldehyde, CgHgOj, is a methyl ether of para-oxy-benzaldehyde, which is found to a small extent in the oils of fennel and aniseed. It is manufactured on an extensive scale artificially, and is the basis of all the perfumes of the hawthorn or May blossom type. It is known commercially as aubepine . A certain amount of anisic aldehyde is obtained as a by-product in the manufacture of coumarin, but the greater- part of it is obtained by very careful oxidation of anethol, the characteristic constituent of aniseed oil, which has the constitution—... 

Anethol (isoestragol, methyl-y-oxy-propenyl-benzene) is the principal constituent of aniseed and star aniseed oil, and occur to a considerable extent in fennel oil. It is a crystalline solid, having the characteristic odour of aniseed oil, and possessing the following characters —... 

C10H12O, Mr 148.20, tranx isomer pioi.vkPa 234°C, pi.6kPa H5°C, df 0.9883, 1.5615, occurs both as its cis and trans isomers in nature however, /ran -anethole is always the main isomer. Anethole occurs in anise oil (80-90%), star anise oil (>90%), and fennel oil (80%). 

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). 

The oil was formerly produced in many countries, mainly in eastern Europe, but has now been replaced, to a large extent, by the less expensive star anise and fennel oils which also contain a high percentage of anethole. 

Fennel oil is mainly used in flavoring oral care products and in pharmaceutical preparations. A reasonably quantity of fennel oil is used for the production of pure anethole for flavouring alcoholic beverages (anise liqueurs) [513dj. FCT 1976 (17) p.529 [8006-84-6], [84625-39-8]. 

Bitter fennel Foeniculum vulgare MU , subsp. vulgare var. vulgare ( )-Anethole (55-75), fenchone (12-26), limonene (1-5)... 

Foeniculum officinale All. F vulgare Mill. Xiao Hui Xiang (Fennel) (fruit) Anethol, d-fenchone, anisaldehyde, methylchavicol.33 Restore normal functioning of the stomach. 

Determination of the phenols is of special importance in the analysis of hop (carvacrol), thyme, ajOwan (thymol), aniseed, badiana, fennel (anethole), clove bud and stem (eugenol) and sassafras oils (safrole). 

Anethole (80-90%), methylchavicole, terpenes. Oil of fennel, anise terpenes, spermaceti, fatty oils, oil of turpentine. Chief tests solidifying pt., solubility in alcohol... 

Fennel Foeniculum vulgare (Umbelliferae/ Apiaceae) ripe fruit 2-5 anethole (50-70) fenchone (10-20) estragole (3-20) flavour, carminative, aromatherapy... 

Fennel oil contains anethole and fenchone, which reduce bloating and in higher concentrations act as antispasmodics. 

It is made by the oxidation of anethole (the chief constituent of anise, star anise, and fennel oils). 

Fennel (Foeniculum vulgare Mill.) Anethole, estragol ch2... 

In a comparative study on hydrodistillation and supercritical C02 (SC-COJ extraction of ground fennel seeds, the former possessed a less intense fennel seed aroma than extracts obtained by SC-C02 from organoleptic tests (Damjanovid et al., 2005). Optimal conditions of SC-C02 extraction (high percentage of trans-anethole, with significant content of fenchone and reduced content of methylchavicol and... 

The root essential oil contains (on average) a-pinene (1.0%), p-cymene (0.3%), /f-lenchyl-acetate (1.0%), trans-anethole (1.6%), eugenol (0.2%), myristicin (3%) and dillapiole (87%). On the other hand, the root and bulbous stem base of Florence fennel contains less than 1% of dillapiole but 70% of trans-anethole, giving a very different taste. The herbage contains 1.00—2.55% essential oil, up to 75% of which is trans-anethole. Anethole and fenchone... 

Many techniques are followed to identify and quantify the components of fennel essential oil. Krizman et al. (2006) developed a headspace-gas chromatography method for analysing the major volatile constituents in fennel fruits and leaves — a-pinene, a-phellandrene, limonene, fenchone, estragole and trans-anethole. 

Fennel oleoresin is prepared by solvent extraction of whole seeds and normally contains a volatile oil of 50% or a guaranteed content in the range of 52-58%. Only small quantities are produced for specific uses as it is not a substitute for fennel oil. Chemical analysis by Barazani et al. (2002) of the volatile fraction of oleoresins from fruits of seven natural populations of F. vulgare var. vulgare (bitter fennel) from the wild and after cultivation indicated the presence of two groups of populations. Chemotypic differentiation (relative contents of estragole and trans-anethole) or phenotypic plasticity increases within-species chemical variability, but the specific ecological roles of these essential oils remain to be uncovered. 

Fennel contains anethole, an antispasmatic, along with other pharmacologically active substances. The various scientifically documented medicinal effects of fennel are listed below. 

Anetholes from fennel, anise and camphor are among the several dietary factors that have the potential to be used to prevent and treat cancer (Aggarwal and Shishodia, 2006). Essential oil of fennel is included in some pharmacopoeias. It is used traditionally in drugs to treat chills and stomach problems. 

Sekizawa and Shibamoto (1982) reported the mutagenicity of anethole present in fennel from their studies. Stich et al. (1981) examined the clastogenic activities (substances or processes which cause breaks in chromosomes) of quercetin from fennel seeds and the ubiquitous transition metal Mn2+ - individually and in various combinations. The clastogenic effects of the simultaneous application of arecoline from betel nut, plus quercetin, were greater than the action of quercetin alone. 

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... 

Gross, M., Friedman, J., Dudai, N., Larkov, O., Cohen, Y., Ravid, E.B.U., Putievsky, E. and Lewinsohn, E. (2002) Biosynthesis of estragole and t-anethole in bitter fennel (Foeniculum vulgare Mill. var. vulgare) chemotypes. Changes in SAM phenylpropene O-methyltransferase activities during development. Plant Science 1 63(5), 1 047-1 053. 

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