Limonene anise

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%). 

Composition According to ISO [19], the oil contains 86-95% E-anethole, up to 1.0% Z-anethole and up to 6.0% methyl chavicol. Eoeniculin can occur up to 3.0%, anisic aldehyde is limited to 0.5%. Further constituents are monoterpenes like a-pinene, a-phellandrene, limonene, linalool and a-terpineol. Besides P-caryophyllene, two further sesquiterpenes are typical trace components for Chinese star anise oil, namely E-and Z-a-bergamotene. 

Composition E-anethole (bitter fennel 55-75%, sweet fennel 80-95%), fenchone (bitter fennel 12-25%, sweet fennel below 1%), methyl chavicol (2-6%), limonene, a-pinene, a-phellandrene, cis-anethole and anisic aldehyde. For further constituents see [99,100]. Ravid et al. ]101] employed chirality GC to prove that enantiomerically pure (-i-)-fenchone is present in fennel oil. 

Star anise essential oil isolated by HD and SEME is dominated by trans-anethole (oxygenated compound) - 78% and 81.4%, respectively. Limonene, the second most important compound, is only present at 11.6% and 6.6%, respectively, in the oils obtained by HD and SEME. Cumin essential oil isolated by SEME or HD contains the same five dominant compounds but in different quantitative amounts -cumin aldehyde (37.4% and 22.8%, respectively), a-terpin-7-enal (29.1% and 14.4%), y-terpinene (12.9% and 22.3%), p-cymene (12.1% and 18.4%), and f>-pinene (5.9% and 16.2%). Ajowan essential oil isolated by SFME is characterized by a substantial amount of the oxygenated monoterpene thymol (60.3%) whereas the oil extracted by HD is dominated by three compounds in relatively similar amounts - thymol (35.4%), p-cymene (29.2%) and y-terpinene (28.6%). y-Terpinene and p-cymene are also present in the essential oil extracted by SFME, but in smaller amounts - 16.4% and 21.2%, respectively. 

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. 

Although this oil should be produced solely from fruits, more often the whole aerial parts are used. Adulteration is done by synthetic anethole or from other sources like star anise oil. Blending is done too with star anise oil and limonene + 60°. Analysis is done by GC-MS or by multidimensional enantiomeric separation. According to Ravid (1992), the chiral ratio of (+)-fenchone is 100%-0%. 

Many essential oils, such as those of citrus fruits, contain terpene hydrocarbons which contribute little to aroma but are readily au-tooxidized and pol)merized ( resin formation ). These undesirable oil constituents (for instance, limonene from orange oil) can be removed by fractional distillation. Fractional distillation is also used to enrich or isolate a single aroma compound. Usually, this compound is the dominant constituent of the essential oU. Examples of single aroma confounds isolated as the main constituent of an essential oil are 1,8-cineole from eucalyptus, 1(—)-menthol from peppermint, anethole from anise seed, eugenol from clove, or citral (mixture of geranial and neral, the pleasant odorous... 

The following bodies have been detected in star aniseed oil Dextro-o-pinene, phellandrene (in several" modifications), cymene, cineol, di-pentene, Z-limonene, a-terpineol, methyl-chavicol, hydrokinone ethyl ether, safrol, a sesquiterpene, anise ketone CgH (OCH3)(CH3. CO. CHj), and anethol. 

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). ° ... 

Rue oil contains varying amounts of 2-nonanone, 2-decanone, and 2-undecanone (methyl-n-nonyl ketone) as major components, with 2-undecanone about 90% in Algerian me oil.Other components include 2-heptanone, 2-octanone, 2-nonanol, 2-unde-canol, undecyl-2-acetate, anisic acid, phenol, guaiacol, small amounts of coumarins (bergapten, herniarin, and xanthotoxin), monoterpenes (cineole, a- and P-pinenes, limonene), and others (karrer jiangsu martindale). 

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