Methyl Salicylate-d4

Methyl salicylate-d₄ is intended for use as an internal standard for the quantification of methyl salicylate by GC- or LC-MS. Methyl salicylate is a phenol that has been found in Narcissus and has diverse biological activities.^1,2,3,4,5 It scavenges free radicals in a Trolox equivalent antioxidant capacity (TEAC) assay (IC₅₀ = 0.27 ?M).² Methyl salicylate (10 mg/ml) is active against E. coli and S. aureus.³ It activates transient receptor potential ankyrin 1 (Trpa1) and Trp vanilloid 1 (Trpv1) in CHO cells expressing mouse Trpa1 or rat Trpv1 when used at concentrations of 0.6 and 2 mM, respectively.⁴ Methyl salicylate does not induce gastric ulcers in cold-stressed rats and inhibits carrageenan-induced paw edema (ED₅₀ = 220 mg/kg) and yeast-induced fever in rats.⁵ Formulations containing methyl salicylate have been used as topical analgesics, oral antiseptics, and food additives.

References:
[1]. van Dort, H.M., J?gers, P.P., ter Heide, R., et al.Narcissus trevithian and Narcissus geranium: Analysis and synthesis of compoundsJ. Agric. Food Chem.41(11)2063-2075(1993).
[2]. Battino, M., Ferreiro, M.S., Fattorini, D., et al.In vitro antioxidant activities of mouthrinses and their componentsJ. Clin. Periodontol.29(5)462-467(2002).
[3]. Khiati, Z., and Othman, A.A.Synthesis and antibacterial activity of 1,3,4-oxadiazole and 1,2,4-triazole derivatives of salicylic acid and its synthetic intermediatesS. Afr. J. Chem.6020-24(2007).
[4]. Bandell, M., Story, G.M., Hwang, S.W., et al.Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykininNeuron41(6)849-857(2004).
[5]. Rainsford, K.D., and Whitehouse, M.W.Anti-inflammatory/anti-pyretic salicylic acid esters with low gastric ulcerogenic activityAgents Actions10(5)451-456(1980).