210555-50-3Relevant articles and documents
Identification of a Novel TRPM8 Agonist from Nutmeg: A Promising Cooling Compound
Shirai, Tomohiro,Kumihashi, Kentaro,Sakasai, Mitsuyoshi,Kusuoku, Hiroshi,Shibuya, Yusuke,Ohuchi, Atsushi
, p. 715 - 719 (2017)
The transient receptor potential melastatin 8 (TRPM8) ion channel is the primary receptor for innocuous cold stimuli (8′-7-ethoxy-4-hydroxy-3,3′,5′-trimethoxy-8-O-4′-neolignan (1) with an EC50 of 0.332 μM, which was isolated from a well-known spice, nutmeg (Myristica fragrans Houtt.). Structure activity relationships are also disclosed, showing that the 7-d-menthoxy derivative is the most potent agonist (EC50 = 11 nM). The combination of 1 and l-(-)-menthol has an additive effect, suggesting that neolignan compounds interact with TRPM8 at different sites from those of l-(-)-menthol.
A novel synthesis of isoeugenol, [ring-(U)-14C]
Immoos, John E.
, p. 419 - 424 (2015/11/18)
A novel method for the preparation of isoeugenol, [ring-(U)-14C] is presented. Phenols and phenyl esters substituted in the para position with 1-hydroxyethyl or 1-hydroxypropyl acetate esters when treated with 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide (DMF) eliminate the alkyl carboxylate function to give the unsaturated compound. The reaction fails with unsubstituted or ether substituted phenyl 1-hydroxyacetate esters.