4- Hydroxy-2-methylbenzoic acid

Collie s hypothesis that aromatic compounds are made biologically from ethanoic acid was greatly expanded by A. J. Birch to include an extraordinary number of diverse compounds. The generic name acetogenin has been suggested as a convenient classification for ethanoate (acetate)-derived natural products, but the name polyketides also is used. Naturally occurring aromatic compounds and quinones are largely made in this way. An example is 2-hydroxy-6-methylbenzoic acid formed as a metabolite of the mold Penicillium urticae ... 

Degradation procedures analogeus to those used for mycobactin P (see above) showed the aromatic residue to be salicylic acid (2-hydroxy-6-methylbenzoic acid in mycobactin P) and the hydroxy acid to be (+)-( -hydroxybutyric acid ((-)-3-hydroxy-2-methylpentanoic acid in mycobactin P). Fatty acid side chains substantially different from those in mycobactin P a minor component contains a s-octadec-2-enoic acid (identical to the principal product in mycobactin P). The major substituents in the fatty acid side chain are Cis to C21 fragments of unknown constitution. 

Studies in relation to biosynthesis, 2-hydroxy-6-methylbenzoic acid in Penicillium griseofulvum, A.J. Birch, R.A. Massy-Westropp and C.J. Moye, Aust. 

From the beginning It was feasible that the formation of the salicylic moiety in the Ci5 series was likely to be similar to that of 2-hydroxy-6-methylbenzoic acid (6-methylsalicylic acid) in Penicillium grisofuMum (ref.86) although, remarkably, the interesting case of Anacardium occidentale found no mention in one account (ref. 

Other routes to the parent orsellinic acid have been listed (ref. 119). Cycloaromatisation reactions have been employed for the synthesis of 2-hydroxy-6-methylbenzoic acid and for the 4-methyl isomer as shown in the scheme The syntheses which are claimed to be regiospecific involve two different pathways in the reaction of 4-methoxybut-3-en-2-one with the bis-trimethylsilyl ether of 1-methoxybuta-1,3-diene, dependent on the conditions used (ref. 120). 

In more recent years, the need to create molecular diversity for peptide libraries has resulted in somewhat of a renaissance for the 4-hydroxy-methylbenzoic acid linkage agent. The ability to cleave the peptide-to-resin ester with many nucleophiles including hydroxide, alkoxides, and primary amines has added to the library workers arsenal. 

In order to remove 1-3 g. of contaminating 2-hydroxy-3-methylbenzoic acid, the crude acid is ground in a mortar and refluxed briefly with 100 ml. of chloroform, and the suspension is filtered hot (Note 9). The separated solid is dried in air and added to 1 1. of boiling water. Fhe mixture is boiled gently for 15 min-... 

Hydroxyisophthalic acid has been prepared by oxidizing 2-hydroxy-3-methylbenzoic acid with lead dioxide, by cleaving the ether group of 2-methoxyisophthalic acid with hydriodic acid, and by hydrolyzing 2-iodoisophthalic acid with alcoholic sodium hydroxide. ... 

Oxidation, of Grignard reagents with peresters, 41, 91 43, 55 of 2-hydroxy-3-methylbenzoic acid to 2-hydroxyisophthalic acid by-lead dioxide, 40, 48 of indene, 41, S3... 

Roberts DJ, PM Fedorak, SE Hrudey (1990) COj incorporation and 4-hydroxy-2-methylbenzoic acid formation during anaerobic metabolism of m-cresol by a methanogenic consortium. Appl Environ Microbiol 56 472-478. 

C8H8N2 2-methyl-1 H-benzimidazole 615-15-6 68.25 1.0605 2 13460 C8H803 2-hydroxy-3-methylbenzoic acid 83-40-9 47.17 1.2172 2... 

C8H8N2 1-methyl-1H-indazole 13436-48-1 99.00 1.0315 1 13461 C8H803 2-hydroxy-4-methylbenzoic acid 50-85-1 47.17 1.2172 2... 

C8H8N2 2-methyl-2H-indazoie 4838-00-0 99.00 1.0450 1 13462 C8H803 2-hydroxy-5-methylbenzoic acid 89-56-5 47.17 1.2172 2... 

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