175796-45-9Relevant articles and documents
Structure–activity relationships of vanillic acid ester analogs in inhibitory effect of antigen-mediated degranulation in rat basophilic leukemia RBL-2H3 cells
Ishimata, Nao,Ito, Hideyuki,Tai, Akihiro
, p. 3533 - 3536 (2016)
Methyl vanillate (1) showed strong degranulation inhibitory activity among vanillin derivatives tested. In order to find structure–activity relationships for developing anti-allergic agents with simple structures and potent activity, we synthesized several vanillic acid (VA) ester derivatives with C1–C4and C8alkyl chains and evaluated their degranulation inhibitory activities. The most active compound of VA ester derivatives was derivative 5 with a C4straight alkyl chain, and derivative 5 exhibited approximately three-fold greater inhibitory activity than that of 1. Moreover, we designed 8 types of analogs based on 5, and we found that the minimum structure for potent degranulation inhibitory activity requires direct connection of the butyl ester moiety on the benzene ring and at least one hydroxyl group on the benzene ring. Butyl meta or para hydroxyl benzoate (10 or 11) has a simpler structure than that of 5 and exhibited more potent degranulation inhibitory activity than that of 5.
Vanillic acid ester perfuming agents
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, (2008/06/13)
The vanillic acid esters, for example, methyl or ethyl vanillate, are effective perfuming or olfactory agents for a wide variety of compositions, substrates and articles, whether perfumes, skin- and haircare products, cosmetics, shaving preparations, toiletries, deodorants and antiperspirants, room deodorizers, etc.