Hi, @Rastan! I am actually very curious about this, and I’m really happy to find someone to ask about it! Can you tell me what part of the molecule deprotonates under alkaline conditions? Does the 2nd hydroxyl group have as labile a proton as the first, but only after the first one goes ketone? Why does the position para to that first ketone oxygen also get an added oxygen atom? I’m guessing the color is due to the conjugated region, but you mentioned the dimer… I am especially curious about that, because I have seen 2 things:
First, the formation of purple in situ with a CBD distillation (containing a bit of MgO) upon intentionally allowing air to enter, and then what appeared to be a reversal of the color back to normal upon sealing the air off again…
Second, several instances of the actual alkaline beam test (KOH in EtOH dropped into CBD:hexane solution) giving a strong purple color that eventually faded to a more pink color over time…
Is HU-331 monomer a different color than the dimer?
I am really not that knowledgeable, I am just cribbing off of this article. The HU-331 is the monomer. I would assume that both hydroxels on CBD are equally likely to deprotonate, looking at how they are symmetric in relation to the limonene part of the molecule. What I don’t know is if both have to be de-protanated for the oxidation to proceed or if one is enough. I haven’t seen anything on the Pks of the two or the reaction kinetics vs. pH and I don’t know enough about this type of chemistry to do anything more then guess at that. Also the original paper from 1968 is here. I don’t have an Elsiver so I can’t tell you how informative it is.
The oxidation is a two step process where CBD → 5’hydroxy-CBD → HU-331 + dimer. According to this work, the 5’hydroxy-CBD has a spectra intermediate to the colorless CBD and the HU-331. This could be the pink color if the HU-331 isn’t very stable in alkaline conditions or if the HU-331 is being reduced back to the 5’hydroxy-CBD? I want to eventually want to purify some of the hydroquinone to use as an HPLC standard but I haven’t taken the time yet. When I do I might play around with it to see how stable it is.
Hi PN the keto-enol tautormerization forces a lone pair to on to the carbon in the para position. If you use an electrophilic peroxide, the oxygen will from that. If the reaction is open to air, molecular oxygen will eventually give an oxygen in that position as well.
THC-A weight % yield is 54% before final purification. Very Low. I don’t see a logic behind using non-polar solvent TBME for pulling THC-A salts from the aqueous layer before acidifying to THC-A. The yield gets hit twice during the non-polar → polar → non-polar transition
Is there any potential for using ion exchanger resins, similar to those used to remove minerals from potable water prior to addition to a reactor coolant loop, to pull cannabinoids? This may be a completely ignorant question, haven’t been in nuclear power for 8 years and I can’t remember the makeup of our resin beads.
Most likely yes if one can make the desired cannabinoid have a diffrent polarity or the undesired
Back to partial decarboxilation
Still haven t mastered that
Probably a dumb question but why don’t we have a mobile app for future4200 and good life gang? @Future Continue growing the community worldwide with easier access
Continue growing the community worldwide with easier access