71186-03-3

Upstream product

• 52144-91-9 3,5-bis(benzyloxy)diazoacetophenone 
• 100-44-7 benzyl chloride 
• 28917-44-4 3,5-dibenzyloxylbenzoyl chloride 
• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 28924-18-7 2-bromo-1-[3,5-bis(phenylmethoxy)phenyl]ethanone 
• 58605-10-0 methyl 3,5-bis(benzyloxy)benzoate 

Downstream Products

• 71186-04-4 3-(3,5-dibenzyloxybenzoyl)propionic acid 
• 71186-09-9 methyl 4-(3,5-dihydroxyphenyl)butanoate 

Relevant academic research and scientific papers

A urinary metabolite of Δ1-tetrahydrocannabinol. The first synthesis of 4''-hydroxy-Δ1-tetrahydrocannabinol-7-oic acid labelled with deuterium

The first synthesis of 4''-hydroxy-Δ1-THC-7-oic acid, one of the three major metabolites of Δ1-THC identified in human urine is discussed. Methyl 4-(3,5-dihydroxyphenyl)butanoate (8) was prepared from 3,5-dihydroxybenzoic acid in an overall yield of 15%. 8 was condensed with a terpene synthon (9) under acidic conditions followed by hydrolysis and conversion of the 4''-carboxylic acid function to the corresponding methyl ketone using methyllithium. Reduction with NaBH4 afforded the secondary alcohol in the side-chain. Acetylation and removal of the 1,3-dithiane masking group gave the aldehyde in C-7-position which was further oxidized using NaClO2 followed by deacetylation to give the desired metabolite 14. The same procedure may be used for the synthesis of unlabelled 4''-hydroxy-Δ1-THC-7-oic acid.

Synthesis and psychotropic activity of side-chain hydroxylated Δ6-tetrahydrocannabinol metabolites

Syntheses of the five side chain mono-hydroxylated Δ6-tetrahydrocannabinol derivatives are described. On the basis of behavioural tests with these compounds in rhesus monkeys, it was concluded that hydroxylation at the benzylic C-1' position sharply reduces 'Cannabis tup' activity annabis ttypactivity as compared to Δ6-THC; that on C-2' causes some reduction in activity, whereas hydroxylations at the other positions cause no changes.