Well…yes THCA has its own pKa property…for the carboxylic acid moiety.
If it were to interact with an amine …which also has its own pKa.
It is all dependent on the pH, what exact complexes can be made.
All told, all weak acids and weak bases act together to effect a buffer action with regards to pH of the total solution.
But they also act together h-bonded solution networks.
Or ion pairs…I have posted paper references on all the different forms of carboxylic acids In both protic and aprotic solutions. (Often using Salicylic Acid as a model for cannabinoic Acids).
Now this post is about the Trichome storage area environment…
Which based on the data posted in that patent…suggest basically a protic environment slightly modified by organics (terps?)…
And notes enzyme rates at different pH…4-8.
So here we appreciate THAT mixture or solution…say pH 4.5 protic, trichome volume playing field…with terpene and polyol antifreeze.
As soon as you freeze the H20 solid at -50 and extract that mess with Butane…surprise…it all goes into solution.
However what ever held that protic solution together in the trichome protic environment at the trichome concentration of cannabinoic acid….let us just amuse ourselves with a Hydrotrope action, which is concentration dependent….is all obtained by concentration levels in the Trichome Volume Element.
When you extract that trichome volume element with your butane extraction volume element, there must be (guessing) a 1000 fold dilution of that volume element…so any concentration and pH dependent hydrotope like action that prevailed in the Trichome volume element is gone….AND
the entire solution now rearranges to the aprotic-nonpolar volume element of the Butane (butane contaniminated with water and a thousand other things, not exactly butane and 1000x diluted…moreover, the prevailing solvent is now aprotic and everything you ever knew or thought about pKa’s is out the window…that is we don’t think hydronium ions we think in terms of non disassociated acid monomers, dimers and heterologous [R-COO- _ RCOOH) dimers and homologous conjugates in solution and even R-COO- perhaps in solution shielded or complexed with water, amines, alcohols and amides….and the whole new solution as some sort of fragile h-bonded network.(zoo)
The pKa of R-COOH in this aprotic, non-polar butane-system may be as high as 10-11 This would mean all the COOH are neutral (H)…so where do the H come from if this is the case?
If not, some how the homologous conjugate dimers might crystallize. ??? Big question marks???
Honestly I am back to What is a medusa crystal/ We know THCA is a 99% pure chalk when it wants to be. The rest I have no idea considering possibilities of salts. Every THCA analysis should be accompanied by ICP analysis to make sure it is not an inorganic salt. And every hplc analysis should keep in mind possibility of amine salts or heterologous carboxylic acid dimers…if your final acid is not washed or precipitated from pH2 HCl…i.e., convincing
Non-organic acid wash…you probably have something else. Remember, redissolving what ever you have in HPLC mobile phase with formic acid
Will only result in rearrangement to THCA(H)…and you will get a nice little pure THCA(H) peak…because you put it in a protic mobile phase that forces that form.
The phenomena where THCA chalk precipitates out on the extraction column filter…should be totally exploited as a “feature”
…
To this aprotic butane “solution” noted above, the medusa people must think about how their methanol and amines may act…especially upon concentration as the butane evaporates.
This is the “Medusa playing field”. Fast crash and medusa phase changes emerge from the dynamics of this system.