Noticed this a little while back but it’s really been grabbing my curiosity lately as we fine tune our d8 conversion. Only large difference with the SOP’s out and what we’re doing is no solvent and higher heat (rxn is done in an hour or less, fuck you domino’s) We only see it when isomerizing cbd. Either to d8 or cbn. It increases as heat/time goes on. Aside from being a butterball turkey pop up indicator that the rxn is done I have not been able to find any corresponding ID. We don’t have mass spec yet.
Here’s what it looks like on a GC chromatogram after the fraction is separated via chromatography:
Came out at 190c. Don’t mind the ratty test. We were doing chroma today so we used a quick 5min test to look at peaks on the fractions. Our calibration is overlaid on this chromatogram. Just pay attention to the red circle.
On one of my previous d8 R&D experiments we took a snapshot every (I think 30 or 60 minutes)
Here’s what it correlates to over time. In this experiment we kept pushing the d8 reaction to see what would happen. We were hoping it would go to CBN or at least make d9 ND. Which it did… but as you can see at the sacrifice of any other usable cannabinoid.
I guess the head scratching was worth it though. Not swinging around our (n)D yet until @kcalabs puts our sample through the paces but have to admit it’s looking promising. I’m going to assume it’s really 97% and 0.2% d9. However we’ve had actual THC bumps show up in house but third party came back ND so
I looked around a little in the forums but haven’t found anything relating to this compound. Anyone gather a guess? Something is telling me there might be some good data with this peak and it’s correlation.
I can upload a photo of the HPLC chromatogram later today but it doesn’t show much. Just a single peak significantly earlier than the cannabinoids. Based on their HPLC chromatogram olivetol is definitely a possibility!
Thank you for sharing! Wondering if the data for the LC here is an analytical scale HPLC? Also wondering do you know where the other more polar cannabinoids elute on the LC chromatogram relative to the mystery peak?
I’d like to see where CBG falls. There’s usually a few miscellaneous CBG isomers which have been helping me wrap my head around what I’m looking at faster. Or CBL/CBDV
it’s not analytical, we use the GC-FID for that (can’t decide to the put MS on the hplc or the GC)… but as where the polar cannabanoids are, it’s that mess to the right of that spectrogram. Specifically d8 at the 5800ml point, d9 cbd and others in the blue to the left of that. Still getting separation dialed in on the column
However no cannabinoid (at this time) has such a low bp that it would come out that early in the GC. I do wonder if it’s a degraded product of a cannabinoid like benzene or something. CBG comes out after d9 on our GC. CBC is the earliest to elude but never that early, so it’s not a typical cannabinoid.
needs verified by kca but looking like it in house. I’m actually recalibrating the GC right now then making another sample to get as close to the calibration point as possible which gives me a dead on sample. (actually it was almost scary when we did this the first time, we had a sample come back from kaycha with a cbd concentration of 64.3 and we tested 64.1, pretty neat)
I’m pretty stoked but not celebrating yet but the chromatogram doesn’t lie.
I originally typed up a much longer post and backspaced it because realistically there are just so many things it could be. Unfortunately there’s a lot of unknowns that usually surround olivetol. A lot of those sesquiterpenes that show up right before the cannabinoids are pretty messy. Just like there’s a lot of unknown cannabinoids in the low 300mw range, there’s a ton of sesquiterpenes in cannabis that still are very ambiguous that you’ll see just before the cannabinoids. I call them the “unicorn sesquiterpenes” in my head but I don’t think the scientific community would accept that one.
Judging by the fact it’s increasing throughout the reaction it’s probably not realistic to guess what it is based off of what I’m used to seeing in natural products. I’ve seen some things pop up that were questionable like CBT acetate, CBL, Tetrahydrocannabiorcol, but honestly everything in that general region is pretty tough to make sense of. If you get more data and it does appear to be a sesquiterpene shoot me a private message since I’d be more useful there than if it it is a cannabinoid. That’s where you see some terpene oxides/humulene epoxide etc show up. Would be neat if it were something simple like caryophyllene oxide or alpha-Caryophyllene Alcohol. But at this point it’s just a shot in the dark for me. Unfortunately it’s more likely to just be some obscure benzene derivative/phenol and way above my head. Going to need to summon the iontrap or Siegel call for this one.
Just looking at it from one other angle… is there any chance there’s a contaminant? (Dioctyl adipate, diethylhexyl phthalate)
Edit: oh, also, nice work on dialing in the reaction. Good to see you’re doing your due diligence on the unknowns.
Thanks! I really want to know more about these reactions and the products created. What may be an unknown or undesirable now may be something of worth (not just monetarily but that would be nice). Positive not a contaminant. It’s repeatable. Actually here’s a chromatogram from 2019 when I was trying to make d9 with citric acid. As you can see we weren’t very successful lol but that peak still shows up. It happens anytime there’s an acid involved it seems.
I’ll probably have to find someone that wants to take a look at it. Actually since we have it in a fraction Im going to evap the solvent and see what comes out. Shit, maybe ill dab it (im kidding)
noproblemo! glad it’s appreciated! I kinda stepped away for a few weeks as I switched gears working on bioavailability enhancements (little humblebrag, can have an edible hit in 4 minutes) but now get to focus again on my passion with the R&D and helping others. I’ve always loved helping others learn, and have a lot to share. And if I can do it with some humor and relatable examples… well it would be selfish of me to not share. We’re all here for each other!
gonna be going over that a few times