Borneol Bomeol

Amomum cardamomum L. A. globosum Lour. A. tsao-ko Roxb. A. villosum L. A. xanthloides Wall. Bai Dou Ku Cao Guo Shan Ren (Siam cardamon, Chinese cardamon) (seed) d-Borneol, bomeol acetate, d-camphor, linalool, nerolidol, terpene.50 Treat pyrosis, vomiting, dyspepsia, pulmonary diseases. Antitoxic, antiemetic, carminative, stomachic. 

Borneo camphor Bomeol. See DL-Bomeol (-)-Borneol Bomeol, (1S,2R,4S)-(-)- (-)-(1S,4S)-Borneol [(1S)-endo-(-)-Borneol. SeeL-Borneol... 

Esters of bomeol are obtained by the action of dry oxalic acid on turpentine under suitable conditions. From these, borneol is obtained by saponification and is oxidised to camphor. Some other acids produce a similar result, as, for example, salicylic and chlorobenzoic acids. 

Bomeol occurs abundantly in nature as a single enantiomer or, less frequently, as the racemate. (—)-Borneol [464-45-9] occurs particularly in oils from Pinaceae species and in citronella oil. (+)-Bomeol [464-43-7] is found, for example, in camphor oil (Hon-Sho oil), in rosemary, lavender, and olibanum oils. 

Bomeol is a colorless, crystalline solid. (+)-Borneol has a camphoraceous odor, with a slightly sharp, earthy-peppery note, which is less evident in (—)-bomeol. Commercial bomeol is often levorotatory ([ajp — 18 to — 28° in ethanol), and contains (—)-bomeol and up to 40% isoborneol. 

Assay for Total Borneol Not less than 8.0% of bomeol (CioHlgO). 

Bomeol (12), on the other hand, undergoes exchange at a much smaller rate (of the order of about 106 times slower) (see Table 1) under identical experimental conditions but undergoes racemization and decomposition at the same time. The rate of heterolysis of borneol is about the same as that estimated for s-butyl alcohol under the same conditions. A detailed explanation of the differences in rate of exchange in bicyclic alcohols requires considerable further work. 

Thymus sp. (thyme) is a common spice that has been extensively studied [116-123]. Thyme is one of the earliest medicinal plants in western herbal medicine. The essential oil isolated from this spice is active in the inhibition of Gram positive and Gram negative bacteria as well as yeast and fdamentous fungi. A major constituent of thyme oil is thymol (91), which has been implicated as the molecule responsible for the activity of this essential oil. Other materials isolated from thyme oil that possess biological activity include carvacrol (92), bomeol (93), p-cymene (37), a-pinene (13) and camphene (94). Thymol (91) was shown to be the most active, followed by carvacrol (92), borneol (93), / -cymene (37), a-pinene (13), and camphene (94) [121]. 

When bomeol or camphor is heated with solid potassium hydroxide to 250-280 °C, ring cleavage of the bicyclic system occurs and the product, campholic acid 68, can be isolated in high yield65-67. Thus, (-)-borneol gives ( + )-campholic acid [( + )-68], which has been used as the hydroxamic acid derivative as a chiral ligand for a vanadium catalyst in the enantioselective epoxidation of allylic alcohols (Section D.4.5.2.4.). 

Europium, and to a lesser extent terbium, complexes of /3-diketones have been studied in solution and in the solid state by means of their fluorescence (luminescence) spectra. As explained further in Section 39.2.10, it is possible to relate the splitting of the Do—> F transitions of Eu " to the symmetry of the emitting complex, and studies of circularly polarized luminescence (CPL) spectra can give related information. Thus a study of EuCls and complexes of Eu with hexafluoroacetylacetone and four other /8-diketones in methanol or DMF showed that while EUCI3 itself had axial symmetry in solution, the complexes had orthorhombic symmetry. The emission spectra of solutions of adducts of Eu(dpm)3 with PhsPO or borneol have been studied at low temperatures where conformal lability is reduced the Ph3PO adduct has uniaxial symmetry but the bulky, less symmetrical bomeol molecule confers lower symmetry on its adducts. ... 

CAS 464-45-9 EINECS/ELINCS 207-353-1 Synonyms Bicycio [2.2.1] heptan-2-ol, 1,7,7-trimethyl-, (1S-endo)- (1S,2R)-2-Bomanol L-2-Bomanol (-)-Bomeol Borneol, (1S,2R,4S)-(-)-(-)-(1S,4S)-Bomeol [(1S)-endo-(-)-Bomeol 1-Bomyl alcohol L-2-Camphanol Linderol Ngai camphor (1S-endo)-1,7,7-Trimethylbicyclo [2.2.1] heptan-2-ol Empirical CioHisO... 

Bomeol, isobomeol, and camphor are the most important members of the bomane (camphane) family of bicyclic monoterpenes. The labeling pattern of borneol and camphor derived from exogenous [2- C]mevalonate and [2- K jgeraniol in intact tissue is consistent with Ruzicka s hypothesis (Fig. 5) (Banthorpe and Baxendale, 1970 Battersby et al., 1972). Soluble enzyme preparations from sage leaves convert [1- H]NPP to (-t-)-[3- H]bomeol in the presence of Mg and, in the presence of NAD, dehydrogenate the bomeol to (-t-)-[3- H]camphor (Croteau and Karp, 1976b). [1- H]GPP was a less efficient precursor of borneol and camphor in this crude preparation. The epi-... 

B. Capture of the carbocation by water, accompanied by rearrangement of the bicyclo-[3.1.1] carbon skeleton to a bicyclo[2.2.1] unit, yields bomeol. Borneol is found in the essential oil of certain trees that grow in Indonesia. 

The oil contains a-pinene, principally the dextro-rotatory variety, d-sylvestrene, cadinene, the acetic ester of either borneol or terpineol and probably dipentene. A small amount of free alcohol (bomeol or terpineol) is also present. 

That the oil contains the following constituents, Z-a-pinene, d-a pinene, Z-limonene, Z-borneol, bornyl acetate and other esters of bomeol, Z-camphor, cineol, salicylic acid, aldehydes, formic, acetic, butyric ( ) and isovaleric acids, a non-volatile acid or lactone, and a blue constituent of high boiling-point. 

The major component of pine oil is a-terpineol (26). Other components in the product include (3-terpineol (154), y-terpineol (155), a-fenchol (156), bomeol (157), terpinen-l-ol (158), and terpinen-4-ol (159), /i-menthadienes (mainly limonene and terpinolene), 1,4-cineole (102), and 1,8-cineole (103). The mechanisms of some of these reactions are shown in Fig. 8.31. The ethers, 1,4- and 1,8-cineole, are also formed by cyclization of the / -menthane-l,4- and 1,8-diols. The bicyclic alcohols, a-fenchol [512-13-0] and borneol (c Wagner-Meerwein rearrangement of the pinanyl carbocation and subsequent hydration. 

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