Y-resorcylic acid

Phenols that have more than one hydroxyl group may be carboxylated with CO2 at atmospheric pressure under basic conditions. The research team of Y.-C. Gao synthesized 3,5-di-fert-butyl-y-resorcylic acid from 4,6-di-fert-butyl resorcinol using the Kolbe-Schmitt reaction under these conditions. The resorcylic acid derivative was needed in order to prepare ternary complexes of lanthanide(lll)-3,5-di-fert-butyl-Y-resorcylate with substituted pyridine-A/-oxide. 

Reid and his colleagues put forward the theory that the anti-inflammatory action of salicylate is due to its power to form metal chelate complexes. On this basis, it would be predicted that 2,6-dihydroxybenzoic acid (y-resorcylic acid) would be an even more potent anti-inflammatory agent. As already seen (page 77), early hopes of increased potency of this compound were not fulfilled. Nevertheless, the fact remains that many anti-inflammatory substances form coloured complexes with ferric ions in circumstances in which chemically related but inactive compounds do not . Salicylate, phenylbutazone and cinchophen behave in this way. Wiesel described metal chelate compounds of the anti-inflammatory glucocorticoids and showed that... 

As examples, / - and y-resorcylic acid afford resorcinol readily when boiled with water.30... 

Dihydroxyheiizoic acid (y-resorcylic acid) [303-07-1] M 154.1, m 167"(dec), pK s 1.05. Dissolve the acid in aqueous NaHC03 and the solution is washed with ether to remove non-acidic material. The acid is precipitated by adding H2SO4, and recrystallised from water. Dry it under vacuum and store it in the dark [Lowe Smith JCAew Soc, Faraday Trans 1 69 1934 1973], [Beilstein 10 IV 1456.]... 

Dihydroxy-m toluic Acid (Z-Methyl-y-resorcylic acid). 

Dihydroxy-p-toluic Acid (Pam-orseU linic acid, arcvnol-4-carboxylic acid, 4-metAyl-Y resorcylic acid). 

Resorcylic acid, see D-00531 y-Resorcylic acid, see D-00533 V-Resorcylidene-2-aminophenylarsonic acid,... 

Compound retention during RP-HPLC depends on the relative hydrophobicity of the sample compounds. As expected, the elution of phenolics for reversed-phase HPLC is in the order of decreasing polarity. Polarity is increased most by hydroxyls at the 4-position, followed by those at the 2- and 3-positions. Availability of the methoxy group and the acrylic substitution reduces polarity and increases retention times (4). Loss of polar hydroxy groups and/or addition of methoxy groups can decrease the polarity within each class of benzoic and cinnamic acid. Also, the presence of the ethylenic side chain in the cinnamic acids can reduce their polarity compared with similarly substituted benzoic acids (6). The elution order for benzoic acids is as follows (Table 1) gallic > a-resorcylic > protocatechuic > y-resorcylic > gentisic > p-hydroxyben-... 

Melhylpyridine (y-Picoline) 143 1 506 = 0 957J 167 231 i8-Resorcylic acid salt. 

The stability constants of uranyl amino- and mercapto-acid complexes have been determined. Among the acids investigated were cysteine, methionine, P-alanine, anthranilic acid, serine, threonine, and JV-ac tylglycine. Stability constants of a series of chloro-, bromo-, iodo-, and nitro-substituted salicylic acid and of o-pyrocatechinic, y-resorcylic, and gentisic acids complexes of UOj" have been measured 1 1 and 1 2 species were identified. It was observed that there was a distinct dependence of stability constant on the charge of the central metal atom in UO ", NpO, and Pu " tropolonato complexes. ... 

Dimeihoxyba(tzoic Acid [y-Resorcylic add dimethyl ether). 

Figure 4. Chromatogram of a mixture of carboxylic acids as the t-butyidimethylsilyl derivatives. GC conditions DB-1 fused-silica capillary column (30 m x 0.32 mm i.d, 0.25 pm), initially at 60 "C for 2 min, then programmed to 280 °C at 4°C/min 0.8 pi sample, injected with split ratio of 15 1 both injector and detector temperatures at 300 °C nitrogen as the carrier gas at 0.9ml/min. Peaks l = formic, 2 = acetic, 3 = propionic, 4 = isobutyric, 5 = butyric, 6 — isovaleric, 7 = valeric, 8 = caproic. 9 = enanthic, 10 = benzoic, 11= caprylic, 12 = lactic, 13 = phenylacetic, 14 = glycollic, 15 = oxalic, 16 = pelargonic. 17 = malonic, 18 = capric, 19 - succinic, 20 - methylsuccinic, 21 = undecanoic, 22 = fumaric, 23 = 5-phenylvaleric, 24 = p-aminobenzoic, 25 = lauric. 26 = mandelic, 27 = adipic, 28 = 3-methyladipic, 29 = tridecanoic, 30 = phenyllactic. 31 = hippuric, 32 = myristic, 33 = p-hydroxybenzoic, 34 = malic, 35 = suberic, 36 = pentadecanoic, 37 = vanillic, 38 = palmitic. 39 = syiingic, 40 = tartaric, 41 — margaric, 42 = a-resorcylic, 43 = p-hydroxymandelic, 44 = y-resorcylic, 45 = stearic. 46 = homogentisic, 47 = protocatechuic 48 = nonadecanoic, 49 = citric 50 = cirachidic acid. (Reproduced from Ref. 299 with permission).

Shao C-L, Wu H-X, Wang Ch-Y, Liu Q-A, Xu Y, Wei M-Y, Qian P-Y, Gn Y-C, Zheng C-J, She Z-G, Lin Y-C (2011) Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus. 1 Nat Prod 74 629... 

Brase, S., Encinas, A., Keck, )., and Rising, C.F. (2009) Chem. Rev., 109, 3903. Resorcylic Acid Lactones A Pluripotent Scaffold with Therapeutic Potential, S. Barluenga, P.-Y. Dakas,... 

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