Acetate bornyl

Bornyl Acetate.—The acetic acid ester is the most important of the series. It is a constituent of pine-needle and rosemary oils, and has a most fragrant and refreshing odour. It is prepared artificially by the action of acetic anhydride on borneol, in the presence of sodium acetate, or by the condensation of borneol with glacial acetic acid in the presence of a small amount of a mineral acid. It is absolutely necessary in the reproduction of any pine odour. It is a crystalline body, crystallising from peDroleum ether in rhombic hemihedric crystals melting at 29°. The optical activity depends on that of the borneol from which it has been prepared. It has the following characters —... 

It is soluble in 3 volumes of 70 per cent, alcohol. The commercial product is usually a mixture of dextro-rotatory and laevo-rotatory bornyl acetate. It should contain not less than 98 per cent, of ester, and... 

Dextro-dihydroverbenol melts at 58° C. and boils at 218° C. it yields an acetic ester, the odour of which recalls that of bornyl acetate. Dextro-dihydroverbenone is produced by the oxidation of the above alcohol by means of chromic acid, or by the reduction of verbenone by means of hydrogen in presence of colloidal palladium. It boils at 222° C. (Djj 0-9685 [a]o + 52-1 9° 1-47535 molecular refraction 44 45) and gives... 

Geranjl, linalyl, and bornyl acetates Menthyl acetate (for peppermint oil) Geranyl tiglate (for roee-geranium oil) Santalyl acetate (for sandalwood oil) Sabinyl acetate (for savin oil). ... 

Boswellia serrata olibanum has a chemical composition close to that of both the B. carteri and of B. sacra, but contains compounds that are absent in those from other Boswellia and could be used as markers methylchavicol (38), p-anisaldehyde (47), methyleugenol (70), isocaryophyllene (82), sesquiterpene 91, elemicin (92) and an unidentified diterpene (124) eluting between cembrene C (123) and verticilla-4(20),7,ll-triene (125). It is devoid of (5-caryophyllene (73), a-humulene (78), caryophyllene oxide (95) and bornyl acetate (50). 

Valerian extracts show sedative and anxiolytic effects. Whereas passionflower and chamomile have relatively specific anxiolytic effects, valerian shows more general sedative effects, but all effects occur in a dose-dependent manner (Della Logia et al. 1981 Leuschner et al. 1993). The sedative effects of valerian extract are moderate when compared to diazepam and the neuroleptic chlorpromazine (Leuschner et al. 1993). However, valepotriates reverse the anxiogenic effects of diazepam withdrawal in rats in the elevated plus maze. This effect is dose dependent, effective at 12 mg/kg but not 6 mg/kg. Interestingly, the fragrant valerian compound bornyl acetate has sedative effects in mice, but only when inhaled (Buchbauer et al. 1992). 

Buchbauer G, Jager W, Jirovetz L, Meyer F, Dietrich H. (1992). [Effects of valerian root oil, borneol, isoborneol, bornyl acetate and isobornyl acetate on the motility of laboratory animals (mice) after inhalation]. Pharmazie. 1992 Aug. 47(8) 620-2. 

Meadow vole White spruce Pioeaglauoa, /3-Myrcene and bornyl acetate... 

Kreis R Juchelka D, Motz C, Mosandl A, Chiral compounds in essential oils, DC Stereodifferentiation of borneol, iso-borneol and bornyl acetate, Dtsch Apoth Ztg, 131 198 1987, 1991. 

Money et al. have accomplished the chemical functionalization of (-)-bornyl acetate, to yield (206) as the major product with smaller amounts of the 3-keto- and 6-keto-isomers of (206) and exo-(207 R = Ac), as well as microbiological hydrox-ylation using Helminthosporium sativum, to yield endo- and exo-(207 R=H) 6-exo-hydroxybofneol (208 R=H)/5 1 2/ ... 

Esters mainly derived from cyclic terpene alcohols, especially the acetates, are common fragrance and flavor components. Menthanyl, menthenyl, bicyclic bornyl acetates and a few acetates of sesquiterpene alcohols are extensively used in perfume and aroma compositions. 

Bornyl acetate [5655-61-8] is a characteristic component of most conifer oils. It has a camphoraceous, pine-needle-like odor. Both (+)-bornyl acetate [20347-65-3] and (-)-bornyl acetate form colorless crystals the racemate [36386-52-4 ] is a colorless liquid. Bomyl acetate is prepared by esterification of borneol with acetic anhydride or via the process described under borneol (see p. 59). 

Pinaceae needle oils from Pinaceae species contain (—)-bornyl acetate as their main odoriferous component. Other main constituents are monoterpene hydrocarbons such as a- and /3-pinene, limonene, 3-carene, and a- and /3-phellandrene [713-718b]. The oils are used in perfumes for soap, bath products, and air fresheners and in pharmaceutical preparations. 

The main component of the oil is (—)-bornyl acetate, but it also contains other bornyl esters (e.g., bornyl isovalerate), terpene and sesquiterpene hydrocarbons, as well as free isovaleric acid, which contributes strongly to the odor of the oil [807-807b]. 

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