3-Methylsalicylate

Mayriella overbecki W-PG Trail following Methyl 6-methylsalicylate 68 [180]... 

Within Hymenoptera, pheromones produced by workers in social colonies are the best studied across many genera, principally in ants [6], with those eliciting trail following most extensively studied. The distinct behavior and the relative ease of the bioassay have resulted in chemical identifications in many species [ 113,114]. Those that have been recently identified are listed in Table 5. In addition, several alarm and recruitment signals have recently been identified. Many of the compounds recently identified in ants have previously been reported as trail or alarm pheromones in other ant species. For example, methyl 4-methylpyrrole-2-carboxylate 64, 3-ethyl-2,5-dimethylpyrazine 65, (9Z)-hexadec-9-enal 66,4-methylheptan-3-ol 67, and methyl 6-methylsalicy-late 68 have been identified as trail pheromone components, and heptan-2-one 69,4-methylheptan-3-one 70, formic acid 71, undecane 61,4-methylheptan-3-ol 67, methyl 6-methylsalicylate 68, and citronellal 72 have been identified as alarm pheromone components [6]. The use of the same chemicals across genera, with some used for very different functions, is an interesting phenomenon. 

SPENCER, J.B., JORDAN, P.M., Purification and properties of 6-methylsalicylic acid synthase from Penicilliumpatulum, Biochem. J., 1992,288,839-846. 

From recent work, we do know that chemical signals from the seeds direct the ants selections. Although the story is still incomplete, an extraordinary finding has been that a chemical compound called MMS (methyl 6-methylsalicylate) is present in the seeds the ants choose. MMS is found in the seeds of the ten or twelve unconnected species from seven plant families that flourish in Peruvian ant gardens. The ants seem to find this compound irresistible. Offered inert particles coated with MMS, they become excited, pick up these decoy seeds, and occasionally carry them about. 

Phoracantha species contained 6-methylsalicylic aldehyde 191, the dis-ubstituted cyclopentene phoracanthal 192, the corresponding alcohol, phora-canthol, and the (E)- and (Z)-stereoisomers of the saturated system. In addition, methyl and ethyl esters of 2-methylbutyric acid and isovaleric acid as well as the macrocyclic lactones decan-9-olide (=phoracantholide I), (Z)-dec-4-en-9-olide (=phoracantholide J) 193, and 11 -hydroxytetradec-5-en-13-olide 194 [8,355, 356]. As shown by independent syntheses of both enantiomers, the natural phoracantholides show ( -configuration [357]. 

Complexes containing the 3,5-dinitrosalicylate ion, e.g. [Ln2(C2H202N2)3],- H20 (u = 7 -> 15), and methylsalicylate (MesaP ), e.g. [Ln(Mesal)2(OH)-(H2O)] (Ln = La, Pr, Nd, Sm, Gd, Dy, Er, Yb and have been reported. Tris-salicylaldehydato (said ) complexes, Ln(sald)3 (La, Pr, Nd, Sm, Eu, or Tb) form 1 1 adducts with o-phenanthroline (o-phen), aa -bipyridyl, quinoline, and pyridine. The luminescence spectrum of the Eu " complexes showed that, in the solid state, the symmetrically forbidden electric dipole transition intensity was much enhanced for the o-phen adduct when compared to its salicylate analogue. The simple said" complexes were very poor emitters. 

The sex pheromone of the slave-making ant, Polyergus breviceps, has been identified as a blend of methyl-6-methylsalicylate and 3-ethyl-4-methylpentanol. Each compound alone was completely unattractive to males whereas a blend of the two compounds attracted hundreds of males in a couple of hours. 

The scope of the reaction has not yet been developed. It is known that salicylic acid, 3-, 4-, and 5-methylsalicylic acids, and p-hydroxybenzoic acid undergo the reaction, but 3,5-dibromosalicylic acid, 3-nitrosalicylic acid,... 

Gaultheria leucocarpa f. var. cumingiana (Vidal) Sleumer Bai Zhu Shu (leaf) Methylsalicylate, salicylic acid.60 Treat rheumatism, an antiseptic. 

N.A. Gaultheria procumbens L. Methylsalicylate.100 Antiseptic, carminative, diuretic. 

Little information is available regarding tissue distribution or metabolic products of nonsteroidal anti-inflammatory drugs in cattle. The early synthetic compounds were simple derivatives either of salicylic acid such as acetylsalicylic acid and methylsalicylic acid, or of pyrazolone such as metamizole, oxyphenbuta-zone, phenylbutazone, propylphenazone, and suxibuzone. Modern nonsteroidal anti-inflammatory drugs are derivatives either of anthranilic acid such as dido-... 

Methylsalicylic acid, unlike acetylsalicylic acid, is nearly exclusively used as an external rubifacient drug for painful muscles or joints and distributed as ointments or liniments due to their irritating effects on the gastrointestinal mucosa. Absorption through intact skin is possible and has led to prosecution following detection in race-horse urine. 

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