Anethol

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. 

A flavor is tried at several different levels and in different mediums until the most characteristic one is selected. This is important because the character of a material is known to change quaUty with concentration and environment. For example, anethole, ben2aldehyde, and citral taste different with and without acid. Gamma-decalactone has different characters at different levels of use. -/ fZ-Butyl phenylacetate with acid is strawberry or fmity without acid it is creamy milk chocolate. 2,5-Dimethyl-4-hydroxy-3-(2Fi)-furanone with acid is strawberry without acid it is caramel or meat. 

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. 

Pine Oil. This oil is obtained by extraction and fractionation or by steam distillation of the wood of Pinuspalustris Mill, and other species. Most of the oil is produced ia the southeastern United States. The composition of the oil depends on the fractions chosen, but the chief constituents are terpene alcohols, mainly terpiaeol. Piae oil finds use as a germicide ia disiafectants and soaps as an ingredient ia iasecticides, deodorants, poHshes, sweepiag compounds, and catde sprays and as raw material for the manufacture of perfumery-grade terpiaeol [8000-41 -7], anethole [104-46-1], fenchone (137), and camphor (35). 

Sulfation by sulfamic acid has been used ia the preparation of detergents from dodecyl, oleyl, and other higher alcohols. It is also used ia sulfating phenols and phenol—ethylene oxide condensation products. Secondary alcohols react ia the presence of an amide catalyst, eg, acetamide or urea (24). Pyridine has also been used. Tertiary alcohols do not react. Reactions with phenols yield phenyl ammonium sulfates. These reactions iaclude those of naphthols, cresol, anisole, anethole, pyrocatechol, and hydroquinone. Ammonium aryl sulfates are formed as iatermediates and sulfonates are formed by subsequent rearrangement (25,26). 

The majority of the turpentine comes from the southeastern United States, which consists of 60—70% a-pinene, 20—25% P-pinene, and 6—12% other components. Because there is variation in components from different species of the pine tree as well as variation from the many paper pulp mills, there is obviously variation in the analysis of sulfate turpentines. Some of the other components consist of -menthadienes, alcohols, ethers such as anethole [104-46-1] and methylchavicol [104-67-0] and the sesquiterpene hydrocarbon, P-caryophyUene [87-44-5]. 

Many commercial grades of pine oil are available and are specified by physical properties and total alcohol content. Some commercial pine oils and the typical physical properties are Hsted in Table 4. Other grades of pine oil may constitute a blend of synthetic and natural pine oil and give the product a different odor characteristic. The odor difference is caused by the presence of phenoHc ethers anethole and methyl chavicol. 

A good oil nll contain as much as 60 per cent, of anethol, II necessary the crystalline stcaroptene may be separated and enamined, but as a rule added solid bodies ill alter the other characters of the oil. The oil is solnhlfl in an equal volume oI iJO per cent, alcohol. The above tests vlll guard against Ihe ahslraotion of anethol, or the addition of the residue o( oil from which this body has been abstracted. 

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. 

True aoisnnd oil has nOl Leeii solullv iiivesligateA, and I he only bodies so far delected in this oil are anethol, uieilivl-chaOcol, anise ketone, and iranes oI acelic aldehydi.. ... 

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—... 

This reaction serves as a means of identification of estragol. If it be heated for twenty-four hours on the water-bath, with three times its volume of a saturated alcoholic solution of potash, it. is converted into anethol, which, after drying and recrystallisation from petroleum ether, melts at 22°, and boils at 232° to 233°. 

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 —... 

Anethol is the raw material from which most of the artificial hawthorn perfume is manufactured. This perfume consists of anisic aldehyde, known commercially under the name aubepine . 

Anethol dibromide,. OCH3. CjHgBr, melting at 67°, is also a useful crystalline derivative by which anethol can be identified. It is obtained by the action of bromine in chloroform solution on anethol. The product is crystallised from petroleum ether, and then melts at 67°. 

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