28-deMethyl -β-aMyrone

28-Demethyl-β-amyrone (28-Norolean-12-en-3-one) is one of the main triterpenes from Pistacia lentiscus var. Chia[1]. 28-Demethyl-β-amyrone is an antitoxin and can effectively for the toxic effects of Staphylococcal enterotoxins (SEs)[2].

-Carvacrol (100 mg, 1.0 eq) was dissolved in DCM (20.0 mL) and cooled to 0C. To this was added PCC (76 mg, 1.5 eq) and the mixture was stirred at room temperature for 1 hour. The progress of the reaction was monitored on TLC (hexane: EA6:1). The reaction was concentrated on SiO2 and purified by column chromatography, eluting with hexane:EA (60:120:1) to give the pure product 28-demethyl--coumarone (63 mg).

[1] Assimopoulou AN, et al. GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part II. Pistacia terebinthus var. Chia. Biomed Chromatogr. 2005 Oct;19(8):586-605. DOI:10.1002/bmc.484
[2] Kurjogi M, et al. Computational Modeling of the Staphylococcal Enterotoxins and Their Interaction with NaturalAntitoxin Compounds. Int J Mol Sci. 2018 Jan 3;19(1). DOI:10.3390/ijms19010133