Carvacrol methyl ether

Carvacrol (191) was biotransformed to 3-hydroxy- (470), 9 hydros (471), 7-hydroxy- (475), and 8 hydrojQ carvacrol (474), 8,9 dehydrocarvacrol (473), carvacrol 9 oic acid (472), carvacrol-7-oic acid (476), and 8,9-dihydroxycarvacrol (477) by rats (Ausgulen et al., 1987) and microorganisms (Demirci, 2000) including 71 roseum and Cladosporium sp. (Figure 19.80). Furthermore, carvacrol methyl ether (191-Me) was converted by the same fungi to give 7-hydroj - (475-Ac) and 9-hydroxy-carvacrol methyl ether (471-Mc) and 7,9-dihydroxycarvacrol methyl ether (478) (Demirci, 2000) (Figure 19.80). 

FIGURE 19.80 Biotransformation of carvacrol (191) and carvacrol methyl ether (191-Me) by rats. (Modi ed from Ausgulen, L.T. et al., Pharmacol. Toxicol., 61, 98, 1987) and microorganisms (Modi ed from Demirci. R, Microbial transformation of bioactive monoterpenes. Ph.D. thesis, Anadolu University. Eskisehir, Turkey, 2000, pp. 1-137.)... 

Metabolic pathways of menthol (137), menthone (149), thymol (179), and carvacrol methyl ether (202) are summarized in Figure 19.201. Menthol (137) is generally hydroxylated to give 1-hydroxy-(138), 2-hydroxy- (140), 4-hydroxy- (141), 6-hydroxy- (139), 7-hydroxy- (143), 8-hydroxy- (142), and 9-hydroxymenthol (144) and 1,8-dihydroxy- (146) and 7,8-dihydroxymenthol (148) (Asakawa et al., 1991 Takahashi et al., 1994 Van der Werf et al., 1997). Racemic menthyl acetate and menthyl chloroacetate are hydrolyzed asymmetrically by an esterase of microorganisms (Brit Patent, 1970 Moroe et al., 1971 Watanabe and Inagaki, 1977a,b). Menthone (149) is reductively metabolized to 137 and oxidatively metabolized to 3,7-dimethyl-6-hydroxyoctanoic acid (152), 3,7-dimethyl-... 

FIGURE 14.201 Metabolic pathways of menthol (137), menthone (149), /)-cymene (178), thymol (179), carvacrol methyl ether (201), and carvotanacetone (47) by microorganisms and rabbit. 

Main components 1.5-4% essential oil, which contains linalool, bomeol, terpinene -ol, a-terpineol, the methyl ethers of thymol, carvacrol and eugenol, cuparophenol (a phenolic sesquiterpene), sesquiterpene hydrocarbons, cascarilladiene, cascarillone [45, 46] and cascarillic acid ]47], Moreover, cascarilline (bitter constituent), cascaril-line A, vanillic aldehyde, resin, tannins, fat and starch are present. 

Carvacrol, 5-isopropyl-2-methylphenol, 4 mg/mL of mobile phase, 2 mL/S Thymol, 2-isopropyl-5-methylphenol, 4 mg/mL of mobile phase, 2 mL/S Sample Oregano leaves, 10 g/S /-Butyl methyl ether, (HjCjjC-O-CHj, 100 mL/S... 

Refer to Figure E16-1, p. 552. Ten grams of oregano leaves is reflux extracted with /-butyl methyl ether for 20 minutes, and the solvent evaporated at room temperature overnight. The CCC column is filled with stationary phase, and then mobile phase is passed into it. Standards of both thymol and carvacrol are run, and 20 1-minute fractions are collected. The content of each fraction is determined at 276 nm, and their partition ratios are determined. The sample residue is taken up in 5 mL of mobile phase and 0.50 mL is added. The peak area is compared to that shown in Figure El 6-2, p. 552, which was obtained under the same conditions. 

Origanum vulgare Carvacrol, thymol, p-cymene, carvacryl methyl ether, linalool, a-pinene, bornyl acetate, camphor... 

Winter savory S. montana) contains a volatile oil (1.6%) composed mainly of carvacrol, p-cymene, and thymol (total phenols ca. 50%), with lesser amounts of a-and P-pinenes, limonene, cineole, bomeol, and a-terpineol. It also contains triterpenic acids (ursolic and oleanolic acids). Flavonoids include apigenin, apigenin-4-methyl ether, scutellarein-6,7dimethyl ether, and others. ... 

Reactions. Grignard reaction and hydrogenation of the appropriate methyl aryl ketone yielded isothymol.877 Carvacrol was formed in excellent (83%) yield on heating p-menth-l-ene oxide with Pd.878 Aromatic aldehydes can beprotected in situ by formation of a-aminoalkoxides and their O-trimethylsilyl ethers thus 4-formyl-benzoic acid could be protected and elaborated (Grignard reaction) into (264).879... 

Carvacrol (1) Cyolohexene (0.5) Aids (0.16) — 25 3 Carvacryl cyclohexyl ether (15%), cydohexylcarvacrol (20%) 4r4-Amyl-2-isopropyl-5-methyl- 58... 

Calycopterin diethyl ether. 5,4 -Diethoxy-3,6J,8-tetramethoxyflavone, 1342 Calycopterin dimethyl ether. 3,5,6,7,8,4 -Hexamethoxyflavone, 1340 Calycopterol pentamethyl ether. l-(2-Hydroxy-3,4,5,6-tetramethoxyphenyl)-2-methoxy-ethanone, 1340-1341 Carvacrol. 2-Methyl-5-isopropylphenol, 1264 Casticin. 5,3 -Dihydroxy-3,6,7,4 -tetramethoxyflavone, 131 a-Chloroacetovanillone. a-Chloro-4 -hydroxy-3 -methoxyacetophenone, 1384 Chlorflavonin. 3 -Chloro-5,2 -dihydroxy-3,7,8-trimethoxyflavone, 1335 Chlorflavonin dimethyl ether. 3 -Chloro-3,5,7,8,2 -pentamethoxyflavone, 1335 Cladrastin. 7-Hydroxy-6,3, 4 -trimethoxyisoflavone, 1505 Cladrin. 7-Hydroxy-3, 4 -dimethoxyisoflavone, 1487 Creosol. 2-Methoxy-4-methylphenol, 1242... 

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