Oil of anise

Anise oil is obtained from the fruit of Pimpinella anisum, L., which is cultivated chiefly in Russia, but also in Spain, Holland, Bulgaria, France, Turkey, Cyprus and many other places. 

The fruit is greyish-green, but is seldom quite uniform in colour, as the central flower-head has developed first. Immature fruits, chaff seeds of weeds, particles of clay and earth, and coriander which is difficult to eliminate from the fields, are frequently found in anise fruit of commerce, and represent 7 to 8 per cent of foreign substances, and even a higher proportion. 

Anise loses weight in storage, and from 0.1 to 0.2 per cent of its oil per annum. The average yield of oil is from 2 to 3.5 per cent. As in the case of other umbelliferous fruits, it is preferable to crush them before distillation. 

Recent figures for the exportation of anise fruit are difficult to obtain. In 1909 and 1910 the Russian harvest amounted to 200,000 poods, or over 6,000,000 lb. From Cyprus. 150 tons were exported in 1917. Bull. Imp. Inst. 1917,15, 300) 

Bouchardat and Tardy (Compt. rend. 1896,122, 198, 624) examined 22 kilos of commercial Russian oil of feeble dextro-rotatory power. It was cooled to -i-5° and the oil separated from the impure anethole, which showed a rotation of +0° 36, probably due to the presence of 

---

Oil-free alkyds Oil from seeds Oil-in-water emulsion Oil laundering Oil length Oil mining Oil of anise Oil of bergamot Oil of eucalyptus Oil oflemon Oil of Olay Oil of Palma Christi Oil of turpentine Oil Orange Oil-pump Oil reclaiming Oil recovery... 

Benzoic acid in the free state, or in the form of simple derivatives such as salts, esters, and amides, is widely distributed in nature. Gum benzoin (from styrax ben in) may contain as much as 20% benzoic acid in the free state or in combinations easily broken up by heating. Acaroid resin (from anthorrhoca haslilis) contains from 4.5 to 7%. Smaller amounts of the free acid are found in natural products including the scent glands of the beaver, the bark of the black cherry tree, cranberries, pmnes, ripe cloves, and oil of anise seed. Pern and Tolu balsams contain benzyl benzoate the latter contains free benzoic acid as well. The urine of herbivorous animals contains a small proportion of the glycine derivative of benzoic acid, hippuric acid [495-69-2] (CgH CONHCH2COOH). So-called natural benzoic acid is not known to be available as an item of commerce. 

Anethole, C H O, a major constituent of the oil of anise, has the lH NMR spectrum shown. On oxidation with Na2Cr207, anethole yields p-methoxy-benzoic acid. What is the structure of anethole Assign all peaks in the NMR spectrum, and account for the observed splitting patterns. 

Gershbein (1977) reported increases in the liver increment (the amount of tissue regenerated) in partially hepatectomized rats, by subcutaneous (sc) injection of oils of anise, fennel, tarragon, parsley seed, celery seed and... 

The seeds contain some volatile oil, resin and a large amount of fixed oil (Meisner, 1818). The fruit (without the seeds) contains volatile oil, resin, fat, tannin, pectin and mucilage. The volatile oil (oil of star-anise) amounts to about 4-5% and is almost identical with oil of anise (from P. anisum, LinnS). Star-anise oil from Chinese fruit has a specific gravity at 15°C (59°F) of 0.980-0.990 and its known constituents are anethol, phel-landrene, safrol and hydro-quinone-ethyl-ether (Fliickiger, 1879). Poisonous sikimin has been detected in the fruit (Eykmann, 1881), while Schlegel (1885) found a crystalline principle of a pronounced odour of musk. He also found saponin in the watery extract. 

Miething, H., Seger, V. and Hansel, R. (1990) Determination of photo anethole from a stored essential oil of anise fruits as 4,4 -di-methoxystilbene by high performance liquid chromatography ultraviolet coupling. 

Rutovskii, B.N. and Leonov, P. (1 924) Crimean oil of anise. Trav Sci Inst Chim Pharm Moscon 1 0, 64-68. 

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.)... 

SYNS ANISEED OIL ANTS OEL (GERMAN) OIL OF ANISE STAR ANISE OIL... 

Ethers.—Ethers are also constituents of essential oils either as simple ethers or as mixed ether-alcohol or ether-aldehyde compounds. Examples of such oils are oil of anise containing anis aldehyde and anethole (p. 661), and oil of clove which contains eugenole (p. 623). 

Anethol, which has a boiling point of about 235° C. has heretofore been recognized as a constituent of oil of anise and has been derived from anise seed, being used principally as a flavoring. However, anethol has not heretofore been recognized as a constituent of pine oil. 

Properties White crystals sweet taste odor of oil of anise. Affected by light. D 0.983-0.987, refr index 1.557-1.561, optical rotation 0.08, mp22-23C, distillation range 234-237C. Soluble in 8 volumes of 80% alcohol, 1 volume of 90% alcohol almost immiscible with water. 

Caz horated Tincture of Opium. (Paregoric Elixir). This is a camphorated tincture of opium. Macerate X drachm each powdered opium and benzoic acid, 1 fluid drachm oil of anise, 2 ounces clarified honey, and 2 scruples camphor, in 2 pints dilut alcohol for 7 days, and filter through paper. (27. S. Ph.)... 

Anderson s Scott s Pills. Bar-badoes oloos, 24 ounces colocynth, 1 ounce gamboge, 1 ounce Spanish soap, 4 ounces oil of anise, 4 ounce water, a sufficient quantity. To bo made into 3-grain pills. 

Patent Byeentery CordiaL Take of rhubarb, catechu, and camphor, 2 parts each laudanum, 4 parts and a nttlo oil of anise. Dose, 15 to W drops after each operation. 

Take li flnid drachms oil of worm-seed, 3 ounces castor oil, and 10 drops oil of anise mix them together, and add 1 Ouid ounce aromatic syrup of rhubarb. Shako well before using. Dose for a child of 2 years, 1 tea-spoonful night and morning. 

Diarrhea Tincture. Compound tincture of myrrh, 5 ounces tincture of rhubarb, and spirits of lavender, of each 5 ounces tincture of opium, 3 ounces oils of anise and cinnamon, with gam camphor and tartaric acid, of each ounce. Mix. Dose, 1 tea-spoonful in a littlo warm water sweetened with loaf sugar repeat after each passage. This is a magic remedy. 

Spackxoan a Anti-Dyspeptic Fills. Makemto a mass, 6 drachms 24 grains powdered aloes 3 drachms 20 grains each gamboge scammony, and conmound extract of colocynth 96 i ains soap 15 drops each oil of caraway and oil of anise with 1 drachm water. Divide the moss into 16 parts, and make each part into 24 pills 384 pills altogether. A dose consists of 3 pills. 

Fig. 3A, B The major constituent of the essential oils 1-6 is detectable VS reagent as a red-violet to brown-violet zone at R, 0.9-0.95. In the essentia] oil of anise (1), staranise (2), bitter fennel (3) or. sweet fennel (4) it is anethole (Tl) with smaO amounts of the isomer methylchavicol, while basil (5) has predominantly methylchavicol which has the same R, value as anethole. The prominent zone of sassafras oil (6) is safrole (T2). Anethole (Tl) and safrole (T2) can be separated in the solvent toluene (see Fig. 4C), where safrole then shows a higher R, value.

---