Resorcyclic acid

Convert benzoic acid to 3,5-dihydroxybenzoic acid (alpha-resorcyclic acid) (I). 50 g (I), 134 g dimethylsulfate, 60 g NaOH, 300 ml water add 35 g NaOH and reflux to obtain about 50 g 3,5-dimethoxybenzoic acid (II) which is converted to dimethoxybenzoyl chloride (HI) with PCI5. Extract the (HI) with ether and filter. Saturate the ether with NH3 at 0° C and filter. Wash with ether and water and reciystallize from hot water to get 3,5-dimethoxy-benzamide (IV). To a solution of 1 M of n-hexyl bromide (or 1,2-dimethylheptyl bromide, etc.) add 24.3 g Mg in 200 ml ether to... 

In liquid chromatography, reversed-phase materials such as Cig and Cg are the most commonly used sorbents (429, 430, 434, 438, 446, 447, 453, 454). Examples of baseline separations with reversed-phase columns of several groups of anabolics including stilbenes, resorcyclic acid lactones, and other, frequently used anabolics have been reported (463-466). In addition to reversed-phase separations normal-phase separations of anabolics using either Hypersil (467) and Brownlee (456) silica or diol-modified silica have been reported. Although not all analytes were completely separated, the latter column could be efficiently used to differentiate between estrogenic and androgenic compounds within a mixture of 15 anabolics and their metabolites (468). 

Among the major groups of flavonoids in the human diet are the flavonols, proanthocyanidins (which include the catechins), isoflavonoids, flavones, and flavanones. The closely related lignans (resorcyclic acid lactones) have similar properties as flavonoids, and are therefore included here for completeness. Quercetin, a flavonol, is the most predominant flavonoid in the human diet and estimates of human consumption are in the range of 4 to 68 mg/day. Among these studies, the Japanese population had the highest levels of flavonol intake, which was mainly attributed to their green tea consumption. 

This toxin is produced by several Fusarium spp., in particular by the scabby wheat fungus E graminearum (roseum) which also makes deoxynivalenol, DON [71]. It has an unusual macrocyclic sfructure [6(10-hydroxy-6-oxo-trans-l-undecenyl)-beta-resorcyclic acid-jr-lactone] (fig. 7). Zearalenone (also called F-2) is found in the gluten of contaminated wet-milled wheat, and also... 

From the cinnamic acids or phenyl propanoids described above, / -oxidation and truncation of side chains yields a variety of benzoic or simple phenolic acids [28], Rao et al., [22] identified gallic acid (18), gentisic acid (19), protocatechuic acid (20), />-hydroxybenzoic acid (21), oc-resorcyclic acid (22), vanillic acid (23) and salicylic acid (24) in C. arietinum and showed that overall, leaf content of all phenolic compounds was much greater than in roots and stem. They postulated that the production of these compounds may enhance the activity of indole acetic acid oxidase or may express antimicrobial properties when leached into the soil. However, Singh et al. [24] showed that the production of both 18 and 24 by C. arietinum was induced when treated by the culture filtrate of Sclerotium rolfsii along with the phenyl propanoids 14, 15 and 17 mentioned above. 

Table 169. hRf-values of isomeric dihydroxybenzoic acids a-, and y-resorcyclic acids, gentisic (2,5-) and protocatechuic (3,4-) acids... 

Ethyl orthobutyrate added at room temp, to a soln. of 4-(2-hydroxy-1-methyl-propyl)-3-methyl-y-resorcyclic acid in ethyl acetate, and the product isolated after 2 hrs. 1-propylcitrinin. Y 66%. F. e. s. H. H. Warren, M. Finkelstein, and D. A. Scola, Am. Soc. 84, 1926 (1962). 

Patocka, J., Soukup, O., Kuca, K., 2013. Resorcyclic acid lactones as protein kinase inhibitors and naturally occurring toxins. Mini Rev. Med. Chem. 13, 1873-1878. 

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