MOLECULE

Canniprene

Canniprene, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6-) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring leads to stilbenoids. Canniprene is also a derivative of Bibenzyl. Bibenzyl is a compound consisting to two benzene rings linked together via ethane. Bibenzyls typically form a white solid. Bibenzyl forms the central core of several natural products such as dihydrostilbenoids and isoquinoline alkaloids. Canniprene is one of a small number of bibenzyls including 3,4'-dihydroxy-5-methoxybibenzyl and 3,3'-dihydroxy-5,4'-dimethoxy bibenzyl found in Cannabis sativa. Canniprene is neutral, hydrophobic molecule that is not water soluble. Canniprene is commonly found in the fan leaves of Cannabis sativa. The concentration of canniprene in the fan leaves of 160 strains of C. sativa has been measured and wide variations, ranging from traces to >0.2%, have been seen. Canniprene was first reported by Bosch and Salemink to be present in the methylene chloride extract of Mexican cannabis (PMID: 6991645). Canniprene exhibits good ant-nflammatory properties. Studies have shown that it potently inhibits the production of inflammatory eicosanoids via inhibition of the 5-lipoxygenase pathway. In particular, it limits the generation of prostaglandins via inhibition of the cyclooxygenase/microsomal prostaglandin E2 synthase pathway (PMID: 28165233).