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n-Butyllithium has been used to prepare a large number of carbamates of some lower tertiary alcohols, especially of tertiary terpene alcohols, like linalool (5), 1-terpineol (6), cedrol (9), and patchoulol (8) via the corresponding alkoxides. The reaction time in each case was less than an hour, and the isolated yields of most of the carbamates were higher than 85%. The carbamates of synthetic (±)- and genuine (-)-patchoulol (8) were investigated by GC with chiral phases in order to determine their optical purity and degree of racemization. The racemization of (-)-patchoulol after derivatization is less than 3 percent.

Cedrol was hydroxylated by m-chloroperbenzoic acid to give four tertiary alcohols and two secondary alcohols, one of which was converted into an epimer of “senoxydene” in four steps.

A total synthesis of racemic cedrol and cedrene is described in which a key step is the intramolecular Diels–Alder reaction of alkyl cyclopentadiene 3 to give the tricyclic olefin 4. Oxidation of t...

The essential oil of Teucrium polium, growing in Saudi Arabia, was thoroughly investigated for its constituents by GLC-mass spectrometry, TLC, and spectrophotometric methods. This investigation revealed the presence of 10 terpenoidal compounds including the hydrocarbons beta-pinene, limonene, alpha-phellandrene, and gamma- and delta-cadinenes and the alcohols linalool, terpine-4-ol, cedrol, cedrenol, and guaiol. The oil was rich in alcohols and devoid of esters. Preliminary pharmacological screening showed that the oil possesses powerful antispasmodic activity.

1. (1) Shavings from the Eastern Red Cedar (Junuperus virginiana) were examined for three diverse biological properties, i.e. enzyme induction, procarcinogenicity and insecticidal activity. 2. (2) The ability of a cedar environment to stimulate liver drug-metabolizing enzymes in mice was confirmed by lowered values for barbiturate sleeping time. 3. (3) In susceptible strains of mice (C3H-Avy, C3H-AvyfB and CBA/J) the use of cedar shavings as bedding increased significantly the incidence of spontaneous tumors of the liver and mammary gland, and also reduced the average time at which tumors appeared. 4. (4) Cedar and some of its derivatives (Oil of Cedarwood, cedrene, cedrol) disrupted the reproductive and developmental cycle of a number of insects, including the Peanut Trash Bug (Elasmolomus sordidus), the Indian Meal Moth (Plodia interpunctella) and the Forage Mite (Tyrophagus putrescentiae).

n-Butyllithium has been used to prepare a large number of carbamates of some lower tertiary alcohols, especially of tertiary terpene alcohols, like linalool (5), 1-terpineol (6), cedrol (9), and patchoulol (8) via the corresponding alkoxides. The reaction time in each case was less than an hour, and the isolated yields of most of the carbamates were higher than 85%. The carbamates of synthetic (±)- and genuine (-)-patchoulol (8) were investigated by GC with chiral phases in order to determine their optical purity and degree of racemization. The racemization of (-)-patchoulol after derivatization is less than 3 percent.

Publisher Summary The sesquiterpenoids comprise the group of C15 compounds obtained from the vegetable essential oils, that is, the oils of the essence or distillate of plants. This chapter profiles sesquiterpenoid hydrocarbons, such as farnesenes, bisabolenes, zingiberenes and curcumenes, elemenes, santalenes, bergamotene, cuparene, cadinenes, eremophilene, eudalene, the calarane group, the azulene group, himachalenes, humulenes, caryophyllene, and related compounds. It also describes the sesquiterpenoids with an oxygen function such as farnesol, santalols, elemol, cadinols, mustakone; furanoid derivatives, such as atractylon, maaliol, eremophilone; calarane derivatives such as aristolone, drimenol; spiro compounds, such as acorenone, guaiol, and related azulenes, cedrol, widdrol, patchouli alcohol; and macrocyclic types, such as germacrone, valerenic acid, and related compounds. Methods of synthesis, general properties, typical reactions, and the stereochemical aspects of these compounds are also analyzed. α-Santonin is a lactone, the ring of which may be reversibly opened to give the corresponding acid, santoninic acid. The unsaturated ring is readily aromaticized: with hydrochloric acid, α-santonin yields desmotroposantonin. Special importance is attached to the discussion of drimenin and related compounds, lactones related to eremophilane, compounds related to the azulenes, such as guaianolides, costus lactones; abnormal guaianolides such as parthenin; and macrocarbocyclic lactones such as pyrethrosin.

WOS: 000221265200025, The chemical compositions of essential oils from heartwood of the root and stem of Juniperus foctidissima Willd. collected in the vicinity of Eskisehir, Turkey were analyzed by GC/MS. The yield of stein and root heartwood oils were 3.2% and 2.7%, respectively. The main components were found to be cedrol (13-15%), widdrol (9-1.2%). 8,14-cedranoxide (7-8%), 14-hydroxy-(E)-caryophyllene (5-9%), cis-thujopseue (10-11%) and alpha-cedrene (6-8%).

The purity of cedrol, or the total alcohol content of oils of cedarwood, conventionally expressed as “percentage of cedrol,” is normally determined by the formylation method described by Glichitch, for which a reaction time of 72 to 96 hours at 20° to 22° C is used. The results of formylations at higher temperatures, by using gas-liquid chromatography for investigation of the products of reaction, are reported. It is shown that at temperatures not exceeding 45° C the formylation can be substantially completed in 18 to 24 hours without any loss of accuracy.