Thuja 3-Thujone

Thujyl alcohol, Cj Hj OH, occurs in the oils of wormwood and thuja leaves, etc., and also results from the reduction of its ketone, thujone, by means of sodium. It is identical with the body originally described by Semmler under the name tanacetyl alcohol. 

This ketone, of the formula Cj H O, isomeric with those above described, is found in the oils of thuja, tansy, wormwood, and sage. It is identical with the bodies formerly described under the names tan-acetone and salvone. It is best prepared in a state of purity from oil of wormwood. According to Semmler, 200 c.c. of the oil, 0 c.c. of a saturated solution of sodium bisulphite, 75 c.c. of water, and 300 c.c. of alcohol are well shaken at intervals during a fortnight. The crystals formed, consisting of the compound of thujone with the sodium bisulphite, are separated, washed with alcohol-ether, and pressed. On treatment with caustic soda solution, the thujone, amounting to over 40 per cent, of the oil used, separates, and can be distilled with steam. 

The hitherto unanswered question whether the chemically identical thujonas isolated from various essential oils are also physically identical, or whether they are physically isomeric, has now been decided by Wallach in the last-named sense. He has succeeded in establishing the presence of two and possibly of three thujones, although with regard to the third the more probable view is, that it represents a mixture of the other two. His examination has, moreover, proved that thuja oil contains essentially... 

Mention has already been made of the fact that thujone and fenchone do not react with sodium sulphite consequently the method is useless for tansy, thuja, wormseed, and fennel oils. 

Cedar leaf oil (Thuja oil) is produced by steam distillation of fresh leaves and branch ends of the tree Thuja occidentalis L. (Cupressaceae). It is a colorless to yellow liquid with a powerful, herbaceous odor, characteristic of thujone, see p. 217, [314-319a]. 

Biota chinensis Hort. B. orientalis L. (Syn. Platycladus orientalis, Thuja orientalis) Ce Bai Ye (twig) Quercitrin, pinipicrin, thujone, essential oils.33 Hemostatic, shorten blood clotting time, antitussive. 

China Thuja chinensis Hort. T. koraiensis Nakai T orientalis L. Thujene, thujone, fenchone, myricetin, caryophyllene, aromadendrin, quercetin, pinene, hinokiflavone, amentoflavone.48 Antipyretic, asUingent, diuretic, for dysmenorrhea, epistaxis, gonorrhea, metrorrhagia. 

N.A. Thuja occidentalis L. Thujone, flavonoids, wax, mucilage, tannins.99 Antiviral, Ueat warts and polyps. It induces mensUuation. 

It contains Thujone, which could be toxic. Native Americans used thuja for malaria, gout, scurvy, rheumatism, menstrual disorders, and coughs. Thuja s volatile oil acts as a stimulant, a diuretic, and an irritant. Thuja is used for respiratory tract infections and in conjunction with antibiotics in the treatment of bacterial skin infections and Herpes simplex. 

SAFETY PROFILE Poison by intravenous, intraperitoneal, and subcutaneous routes. Moderately toxic by ingestion. Serious physiological consequences from abuse of absinthe (mainly in France) led to its aboKtion in 1915. Wormwood is still used in concentrations of less than 10 ppm in flavored wines. Thujone at 30 mg/kg causes convulsions associated with lesions of the cerebral cortex. Little is known of thujone metabolism. Both forms occur in wormwood oil, oak moss. The a form is major constituent of cedar leaf oil or oil of thuja, sage. The p form occurs in tansy, yarrow. When heated to decomposition it emits acrid smoke and irritating fumes. 

Thujone, Fenchone.—Two other ketone derivatives are known, viz., thujone and fenchone. They occur together in thuja oil. Thujone is present also in tansy wormwood and sage oils while fenchone is found in fennel oil. Without taking up the proofs for the constitution of these two ketones we may give their formulas as below ... 

Limonene inhibiting pine larva parasites feeding (Diprian pini and Dendrolymus pini) [103]. The (+)-3-thujone and (-)-3-isothujone, the main components of Thuja plicata leaves, inhibit the feeding of Pissodes on needle trees [102]. Enzymatic mechanism explaining the olfactory processes are the reasons for eliciting responses between the optical isomers and the receptors. 

Oil of White Cedar. Oil of arbor vitae oil of thuja. Volatile oil from leaves of Thuja occidental is L,., Cupress. aceae. Constit. d-Thujone, f-fenchone, d-pinene. 

Thuja. Arbor vitae yellow cedar false white eedar tree of life. Dried, leafy, young twigs of Thuja occi-dentalis L.. Cupressaceae. Habit. North America cultivated in Europe. Constit. Thujone. fenchone, thujetic acid, tannin, pinipicrin. 

This reaction has been applied for preparative purposes mainly in the hydroaromatic series. For instance, according to Wallach,75 the thujone obtained from thuja oil gives with ammonium formate an aminothujone whose hydrochloric acid salt affords thujene on dry distillation and Harries and Antoni76 obtained 2,3-dihydrotoluene analogously from 1 -methyl-1 -3-cyclohexane-diamine. 

Thuja occidentalis is, as its common name says, endemic to North America Thuja orientalis to China. Both plants, however, are widely spread now worldwide as ornamental plants. There is no difference in the composition of their terpenes. The main component, also responsible for the toxicity is thujon with more than 50 per cent of the essential oil from Thuja. Furthermore fenchone, campher, sabinene, and terpineol-4, tannins and bitter principles are found, too. 

Tegtmeier, M., and G. Hamischfeger. 1994. Methods for the reduction of thujone content in pharmaceutical preparations of artemisia, salvia and thuja. Eur. J. Pharm. Biopharm. 40 (5) 337-340. 

C,oH,jO, Mr 152.24, oil with a menthol-like odor. Bi-cyclic monoterpene ketones with the thujane structure occurring in two C-4-epimeric forms in nature i SAR,5R) -)-a-T, bp. 83.8-84.1 °C (17 hPa), [a]o -19.2° (neat), (15, 4S,5/ )(+)-)S-T., bp. 85.7 -86.2°C (17 hPa), [a]o +72.5° (neat). Not only the names a-and jS-thuJone but also thujone and isothujone are sometimes used incorrectly in the literature. T. are potent neurotoxins, cause epileptic seizures, and can lead to severe psychic damage. It is not yet known if both epimers exhibit the same biological effects. Occurrence Very widely distributed in the essential oils of Asteraceae, Cupressaceae, Lamiaceae, Pina-ceae species. Thuja oil (Thuja occidentalis, Cupressaceae) contains 40% (-)-a-T. and tansy oil (Tanace-tum vulgare, Asteraceae) 58% (+)-/S-T. 

Thujone (21), a major component of wormwood, Artemisia absinthum, was once a major flavoring of the liquor absinthe (Arnold, 1989 Harbome, 1991). At doses of 30 mg/kg of body weight, thujone produces convulsions associated with lesions of the cerebral cortex. Thujone is also a major constituent of cedar leaf oil Thuja occidentalis) and an important component of sage (Salvia officinalis) (Alfaro, 1981). 

Gnilka, R., A. Szumny, and Cz. Wawrzehczyk. 2010. Ef dent method of isolation of pure (-)-a- and (-r)-P-thujone from Thuja occidentalis essential oil. In Program and Book of Abstracts, 41st ISEO Wroclaw, Poland, Lochynski, S. and Cz. Wawrehczyk (eds.), p. 69. 

This oil is often blended with a- and p thujones from cheaper sources like Thuja orientalis. Furthermore camphor or white camphor oil and camphene are used. GC-MS method is used to detect these adulterations. 

ISO standard 9909 shows character and data for this oil. As the main components a thujone p thujone are known, adulteration is done with thuja oil or cedar leaf oil. p Garyophyllene, 1,8 cineole, and borneol from other sources are used. a-Humulene is a marker with up to 12% total content. Detection is done by GG-MS analysis. 

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