Kava Extract/distillate research

[Kingkrunk]

Admins, please know this was also shared in a separate thread, however I believe it may warrant a new topic in and of itself.

I am sharing this, knowing I’ll be ripped to shreds, yet that is the hope - I truly implore more, better educated and equipped individuals and firms to consider looking into this. Theoretical isomerization of lactones is possible as well. Yangonin and kavain have a great deal of potential to either generate revenue or simply “fun” for the users out there.

Please criticize and facilitate/help.

Abstract:

This study is aimed to showcase and request aid to develop a more refined process for extracting and isolating kavalactones from kava root powder using supercritical carbon dioxide (CO2) extraction and subsequently purifying the crude extract through winterization and thereafter utilizing a 5L vacuum short path distillation to obtain a specific kavalactone distillate.

The process was straightforward and relatively basic for most organic extraction operations, nonetheless it involved three main steps: (1) carbon dioxide extraction of kava root powder, (2) crude extract purification through winterization, and (3) distillation of purified crude extract to obtain a kavalactone distillate.

The results of this study showed that the supercritical CO2 extraction of kava root powder was successful once it yielded an orange/waxy crude extract with HPLC testing showing approximately 75.8% kavalactone concentration. The crude extract was then subjected to standard winterization to remove impurities. The purified crude extract was then distilled using a short path distillation apparatus to obtain a kavalactone distillate with a theoretically higher purity and less aromatic/flavorful yield.

Overall, the developed process provides a viable method for obtaining a kavalactone distillate from kava root powder. The use of supercritical CO2 extraction and short path distillation ensures a solventless/high purity end product, which could have potential applications in the pharmaceutical and nutraceutical industries. Further studies are requested so as to help optimize the process and scale it up for commercial production.

Introduction:

Kava, also known as Piper methysticum, is a traditional plant-based medicine used in Pacific island cultures for its relaxing and calming effects. Kava contains a complex mixture of bioactive compounds, including kavalactones, terpenoids, flavonoids etc., which are thought to be responsible for its anxiolytic properties. In recent years, there has been a growing interest in the pharmaceutical and nutraceutical industries to develop kava-based products for various applications. However, the use of kava has been associated with hepatotoxicity and other adverse effects, prompting some regulatory agencies to impose some restrictions on its use. Therefore, there is a need to develop safer and more effective methods for extracting and purifying kava’s psychoactive compounds.

This study and procedure aimed to develop a rudimentary process for extracting kavalactones from kava root powder using supercritical carbon dioxide (CO2) extraction technique and subsequently purifying the crude extract through winterization and lastly, short path distillation to obtain a kavalactone distillate. Supercritical CO2 extraction was chosen as it is both theoretically efficient in separating the lipophilic kavalactones, and CO2 also has the least likelihood of inducing hepatotoxicity or inducing liver conditions. However a solvent was introduced via winterization, yet it was subjected to rotary evaporation thereby removing any residual solvent from the mixture (still, further research is required). Short path distillation, on the other hand, was used as a process to separate the volatiles and purify the heterocyclic ester compounds in fractions based on their boiling points while under a vacuum pressure reduction.

Materials:

• Kava root powder

• Carbon dioxide (CO2) gas

• Super critical fluid extraction (SFE) apparatus equipped with a high-pressure CO2 pump, extraction vessel, separator, and CO2 recovery unit (Ethanol injection

• Winterization solvents, such as ethanol: Filtration sleeve&Vessel: Rotary Evaporator

• Vacuum pump/oil/mist-filter

• 5-liter short path distillation apparatus, including the following components:

  • Heating mantle or hot plate

  • Vacuum pump

  • Cold traps (two)

  • Condenser

  • Thermocouple probe

  • Receiving flask

  • silicone oil or other heating medium (capable of safely maintaining 200C) for the circulating bath

Procedure:

Kava root powder is extracted using supercritical CO2 extraction to obtain a crude extract.

The crude extract is dissolved in a nonpolar solvent and chilled in a safe vessel to -20°C to -80°C to remove impurities through winterization. The solution is then filtered through a filter sieve/paper to separate the precipitated impurities from the solution.

The crude mixture is then taken to a rotary evaporation unit which utilizes silicone oil within the hot bath

The purified crude extract is subjected to short path distillation to obtain a kavalactone distillate with high purity and consistent composition.

The distillation process can be repeated several times to obtain a specific kavalactone distillate with high purity and consistent composition.

The actual process involved three main steps: (1) carbon dioxide extraction of kava root powder, (2) crude extract purification through winterization, and (3) distillation of purified crude extract to obtain a kavalactone distillate. An SFE apparatus was used to extract kavalactones from kava root powder using CO2 gas as the solvent. The winterization process was standard, i.e.: dissolving the crude extract in a suitable solvent, namely ethanol, then using a rotary evaporator - remove all solvent from the mixture. The purified crude extract was then subjected to short path distillation using a 5-liter flask filled to approximately 2.3L worth of material, it is also worth noting that borosilicate raschig rings were packed into the distillation head. Lastly the condenser temperature was tailed/heated using a recirculating bath of hot silicone oil, and two cold traps were used to prevent any loss of material which could be studied and/or corrosion of the vacuum pump itself throughout the course of distillation.

Findings:

Composition: The composition of the initial CO2 kavalactone extract yielded 60-70% total concentration by volume. The composition of the distillate is awaiting results. (Standards can be purchased online, although they are relatively pricey)

-Crude waxy extract

-Kava distillate in receiving flask/on stirrer

Characterization: The kavalactone distillate should be characterized using spectroscopic techniques, such as infrared (IR) or nuclear magnetic resonance (NMR) spectroscopy, to confirm the identity of the individual kavalactones present in the sample. BUT I DO NOT HAVE ACCESS TO THIS EQUIPMENT

Other observations: From the moment of extraction the initial extract the product was dark orange in color and waxy/pasty in consistency. At room temperature, the extract was solid, yet the slightest amount of heat would gradually melt the oil. Winterization yielded a brighter orange color once cooled to room temp, immediately following the rotary evaporation it was a dark reddish color. The heads of the distillate were very light, almost like a pale-yellow - the mains were darker and similar either amber or a reddish amber, lastly and as expected, the tails were extremely red.

Omissions/Final notes:

It must be acknowledged that a great deal of data has been intentionally omitted from this report; because of the nature of intellectual property which is pending certain filings. However, the operators and facilitators of this experiment wished to share the relatively simple nature and straightforward process which yielded an anecdotally “effective” product, to those who may wish to attempt this for themselves. All of this was done in the hopes of improving the market and accessibility of this root and its lactones. We are aware that we have our own intellectual shortcomings, we will never claim to be the best, yet we certainly tried our best nonetheless. Please consider contributing to the research rather than criticizing, we wish to improve and learn ourselves too.

Credits to operation(s) and writing: Daniel H. (KING KRUNK) & Ben W. for consultation and review (Dodi hemp/Indy extractions)

Equipment and materials needed:

PPE

Short path distillation apparatus

CO2 extracted kava

Recirculating heated bath

Heating mantle

Vacuum pump

Thermometer

Weighing scale

Stirring rod

Dry ice

Isopropyl/Propylene glycol

pH meter (optional)

-5L SPD used

Procedure:

Set up the short path distillation apparatus according to the manufacturer’s instructions. Make sure all joints are secure and the apparatus is clean and dry.

Weigh the desired amount of CO2 extracted kava and add it to the distillation flask.

Connect the distillation apparatus to the recirculating heated bath and turn it on. Add high-temperature silicone oil to the recirculating heated bath and set the temperature of the bath to the desired distillation temperature.

Prepare the cold traps by adding a layer of dry ice to the bottom of each trap, followed by a layer of isopropyl 90%. Make sure the traps are securely attached to the distillation apparatus.

Gradually introduce vacuum into the distillation path using the vacuum pump. Monitor the vacuum level readout and adjust the vacuum as needed to maintain a consistent level.

Once total vacuum has been achieved, introduce heat through the heating mantle.

Set the temperature of the recirculating heated bath to be 20C lower than the temperature of the solution in the distillation flask.

Monitor the temperature of the distillation flask using a thermometer. Once the temperature of the solution reaches the desired temperature for distillation, introduce low RPM stirring using the stir bar inside the distillation flask.

Monitor the distillation process closely, collecting the fractions at the appropriate boiling points. Once the temperature of the distillate reaches the theoretical boiling point of kavain (172°C at 150 microns), lower the temperature of the condenser to be 40C below the temperature of the solution in the flask.

Continue the distillation, monitoring the temperature closely and collecting each fraction at the appropriate boiling point. The theoretical boiling points of methysticin, yangonin, and desmethoxyyangonin are 190-192°C, 220-222°C, and 230-232°C, respectively.

As the distillation proceeds, continue to add dry ice to the cold traps as needed to maintain the temperature of the iso-slurry.

Once the distillation is complete, turn off the heat source and allow the apparatus to cool.

Once the apparatus has cooled, carefully remove the receiver and transfer the distilled kava to a clean, airtight container for storage.

(Optional) Measure the pH of the distilled kava using a pH meter. The optimal pH range for kava is 6-8.

Label the container with the date, batch number, and any other relevant information.

Proof of theoretical boiling points:

Theoretical boiling points are typically calculated based on the vapor pressure-temperature relationship of a substance. In this case, we assume that kavain, methysticin, yangonin, and desmethoxyyangonin follow the Clausius-Clapeyron equation, which relates the vapor pressure of a substance to its temperature and enthalpy of vaporization. Using this equation, the boiling points of the four compounds can be calculated based on their enthalpy of vaporization and vapor pressure at a given pressure (in this case, 150 microns).

[Kingkrunk]

Theoretical Isomerizations:

Desmethoxyyangonin(1) + pTsOH ⇆ Kavain(2)

(1) + H+ ⇆ (1-H+) (protonation of carbonyl group)

(1-H+) ⇆ (3) (migration of double bond)

(3) ⇆ (2) (tautomerization to form kavain)

This reaction involves the migration of a double bond from the furan ring to the pyrone ring, resulting in the formation of a different isomer of kavalactone.
the acid catalyst protonates the carbonyl group of desmethoxyyangonin, making it more susceptible to nucleophilic attack by the adjacent double bond. This results in the migration of the double bond and the formation of kavain.

Yangonin ⇆ Kavain

Yangonin (1) + pTsOH ⇆ Kavain (2)

(1) + H+ ⇆ (1-H+) (protonation of carbonyl group)

(1-H+) ⇆ (3) (migration of double bond)

(3) ⇆ (2) (tautomerization to form kavain)

The reaction involves protonation of the carbonyl group in yangonin by the acid catalyst, followed by nucleophilic attack of the double bond on the adjacent carbon atom. This results in the formation of an intermediate molecule, which can undergo tautomerization to form kavain.

Methysticin ⇆ Kavain

Methysticin (1) + pTsOH ⇆ Kavain (2)

(1) + H+ ⇆ (1-H+) (protonation of carbonyl group)

(1-H+) ⇆ (3) (migration of double bond)

(3) ⇆ (2) (tautomerization to form kavain)

This reaction involves the migration of a double bond from the dihydromethylenedioxyphenyl ring to the pyrone ring.The acid catalyst protonates the carbonyl group of methysticin, making it more susceptible to nucleophilic attack by the adjacent double bond. This results in the migration of the double bond and the formation of kavain.
The mechanism of the reaction involves protonation of the carbonyl group in methysticin by the acid catalyst, followed by nucleophilic attack of the double bond on the adjacent carbon atom. This results in the formation of an intermediate molecule, which can undergo tautomerization to form kavain.

---

all intermediate molecules are tautomeric forms of the compounds to be isomerized

See the underlying theme here?

Thinking this over, it seems like with enough cook time in reflux & using heptane as the carrier solvent may yield some thorough lactone isomerization reaction(s)!

Please reach out, I want to learn and work together info@kingkrunk.com 3175489784

Waiting on more capital and will be joining GLG despite our operation having no canna-affiliation

[Kingkrunk]

So, today was an interesting one - Semifail/learning experience

500ml setup via 9.5CFM dial (actual) rotary vane with fresh oil.154g input
Dow corning grease (didn’t have the money for ape.)also my fatal error
Stir bar was high through 60c in solution, knocked down to minimum around 100C in solution to allow the head to catch up and evened her out once we started getting a true distillate rather than a volatile cloud

Path was set, vac fully introduced, it was a race to the top today, ya know- for science. I ALSO thought, “hey I’ll use a claisen, just for shits and gigs/burps” kava really likes to burp.So why not? Also, fatal error

So, all was good, the vac was tight-solution ramped up to 100C within the hour, head was at an 80+C differential yet that is normal for this process (it seems the key is patience, a tight vac and simultaneously speed to completion.). We carried on, and heads/noticeable volatiles “clouds” start spitting out once the head hit 130C, I wrapped up the claisen and BF with some fibers and reloaded the cold trap.

THEN we slowed, hard, head didn’t really want to keep going and I suspected a vac leak or power issue. Turns out it was the former. You see, since it’s kava and not canna/hemp, I’m not worried as much about heat isomerization thus- I sent her bois ,. OH I sent her.

I believe heat degraded my vac grease instead.

Head started plummeting a degree or two here and there, solution wasn’t wanting to exceed 205C-at a 15-20 degree differential with the head (Thermoprobe in the claisen btw)

My distillate yield went from light/heads/volatiles - esque

To a deepened/hombre hue

I kept feeding grease, to my suspected joint leaks and chased as much as I could all the way up to approximately 295C, you read that right
The 15-20 differential held all the way up too ( I found that intriguing)

What I find strange is this
70-90g (accounting for the disty I didn’t blast into the receiving flasks with a heat gun) yield from a theoretical 70% extract input of 154g

The disty is clear and very thin, heads/volatiles esque yet low aroma, very low

Then as we approached the theoretical mains and the differential tightened up to that 15-20 mark, it went dark

THEN the freaking tails crystalized upon exposure to open air and cooling

Bonkers

I’m not the best, but I’m trying

Whispers for science

[MagisterChemist]

Wonderful work. I have been meaning to try this for a long time. I’ll be excited to see the distillate potency results.

[Kingkrunk]

Well. I need more money and a team lol. Money for in house analytics, team so I can learn more quicker I just miss people. Will sell soul for colleagues and friends who are studious AND hungry xD

Lab I sent off to won’t give me the results, but they refunded me so I guess I’m just sitting here waiting for something to give…

I’m guessing I’m on to something however, given that the techs who definitely didn’t test it, reached out asking how this was made.

Unregulated markets are just as much as hemp.

Let’s just learn, make mistakes and improve, get over ourselves and git gud

Since last update - distillate yielded from a 5+/- (C) degree variance between head and mantle, has crystalized in full.

I’ll send kilos of crude out at cost to anyone who has a hankering to do better than me! NOT trying to sell, I feel so alone again and desperately want to find someone to work with

[MagisterChemist]

I will help you out with this. I know many analytical lab managers in Portland personally and I will find someone who will get it tested right for you. DM me. Probably can get some time on a wiped film too if you’d like to try that.

[CrazyGoat]

Congrats for the job!! Very Weill done

Please , I just need to know, how is this smoked/vaped?

This is the propuse right?

Have you made tests In adding this to THCs carts?

What are the results and potential in this aspect ?

[Space_Dandy]

This is interesting. I have had all sorts of kava teas/brews with zero effect? Besides maybe upset stomach and the wish I had drunken a different tea, lol.
There is not a lot of info on the effects of concentrates, I did stumble across:

Toxicity of Kava Kava

Which doesn’t seem promising. What are your takes on toxicity and do people usually experience effects with distillate/concentrate or is this purely for some health benefit?
(It’s a pretty extract you got there in any case.)

[Kingkrunk]

@space_dandy & @CrazyGoat

To answer each in order, as succinctly as possible, inhalant effects were VERY contraindicative to what you would typically expect from kavalactones i.e., very “dopamine-rush” esque feeling, stimulating almost and given the dopaminergic/serotonergic interactions known to occur with kavalactones - I see a great deal of potential marketability with a gaping HOWEVER (which ties into Space_Dandy’s question).

I am HEAVILY concerned about the yields and findings after having ran dozens of short path attempts, to elaborate I am certain some pyrolysis reaction(s) is/are occurring throughout the distillation process.
We’ve been super slammed (thankfully) trying to help other companies bring their brand/products to market - rather than pouring a bunch of time and resources into a likely dangerous market, which I am certainly not wealthy enough or wise enough to spear head.

As far as the bodily and longterm effects of extract vs. standard root consumption(traditional brew) - I’ll say this:
ALL supplements can be medicinal and/or poisonous depending on purity, consumption method/frequency and of course inherent genetic predispositions and sensitivities.
Drink kava tea, ten times a day for years, drink kava extract ten times a day for years - both aren’t necessarily wise as kavalactones are present in each, and all kavalactones must be processed through your liver. Consider the question whether smoking 10 of anything everyday is better than dabbing 10 of anything per day (cold starts not included;) )

I’m not naive to the typical use and application nor the general client whom uses these types of product. I wish all consumers did as much research as you Space_Dandy, the world would be healthier.

[CrazyGoat]

@Kingkrunk

inhalant effects were VERY contraindicative to what you would typically expect from kavalactones

Yes, that’s exactly what I read in some place, if I remember correctly the effects were very calming and maybe sedative?

Therefore my question, maybe be makes it great in dabs, maybe is better than CBD lessening THC paranoia? sometimes there are things that mix really well and people could find it useful and therapeutic.

Both are natural compounds that people recognize, not very crazy if the combo is smooth and siuts really well…
Maybe be is garbage I don’t know.

[MagisterChemist]

I really like Kava effects, but really don’t like the flavor. I am definitely interested in exploring this more. If you think you’re getting pyrolysis from your short path, might be worthwhile to try a wiped film… could achieve a good deal lower of a temperature exposure.

[moronnabis]

Anecdotal appended note you may find amusing: (Wikipedia)
Long term and heavy kava consumption is associated with a reversible skin condition known as “kava dermopathy” or kanikani (in the Fijian language), characterised by dry and scaly skin covering the palms of the hands, soles of the feet, and back.[36][84][85] The first symptom to appear usually is dry, peeling skin; some Pacific Islanders deliberately consume large quantities of kava for several weeks in order to get the peeling effect, resulting in a layer of new skin.[86] These effects appeared at consumption levels between 31 grams (1.1 oz) to 440 grams (0.97 lb) a week of kava powder. Despite numerous studies, the mechanism that causes kava dermopathy is poorly understood “but may relate to interference with cholesterol metabolism”.[85] The condition is easily treatable with abstinence or lowering of kava intake as the skin appears to be returning to its normal state within a couple of weeks of reduced or no kava use.[85] Kava dermopathy should not be confused with rare instances of allergic reactions to kava that are usually characterised by itchy rash or puffy face.[87].

References above are all post 2000…but it was first described by John Papa Ii , circa 1870 in his numerous notes on “Fragments of Hawaiian History”. He described the condition as shedding of your old skin to produce a smooth , parasite free new skin. Such shedding only occurs after 1 or 2 weeks of daily abuse of large quantities.

No like da kine ukus?

[CollectiveObjective]

I actually have this condition right now. Sorta sucks. Been a daily kava user for a long time and the dermatological effects only started for me this yr. Ill ease up, it subsides but every cycle i do this it seems to get worse. Ill drink apx 18-20floz of strong grog an evening. I squeeze in 120F water, noble quality root from Vanuatu or Solomon Islands.

[moronnabis]

HMMM…

I’m not sure but that may qualify as “high as a rat”
In reference to the poor creatures under the Care and Supevision of NIH Laboratories.

[Kingkrunk]

Magister- sir, please forgive my lapse and delay alike - been very busy trying to get the whole foundation for revenue stream up and running as well as some medical stuff that has really ripped the wind from my sails. I have not forgotten and am certain you are right. Please forgive me and hopefully understand friend <3

CrazyGoat- certainly, makes sense and from my experience, mixing the two plants’ alkaloids is very pleasant, albeit a much more different experience than each by themselves. I made an echo chamber post essentially screaming into the void, but the point was “just because we can doesn’t mean we should” lol, not shooting you or your ideas down whatsoever, but for me - I don’t have faith in the consumer market to safely inhale lactones. Look at all the kids still slamming glowies xD

Moro- I’ve thought about this extensively, and while I’m just shooting in the dark, I firmly believe it is a sesquiterpene lactone induced dermapothy and dermatitis. Been trying to figure out which lactone excites the reaction the most. Before doing this I opened a kava bar in IN and both myself and my partner would consistently get it if we made too many personal batches in one day. Chamomile oil seemed to alleviate the scaling reactions as well, more research is needed!

Love and Bula guys

[moronnabis]

When I first read about the exfoliating dermatitis’,I thought…Hmm, imagine shedding your skin like a snake…is this some ancient program imbedded in our genes? Mostly I thought can we make money with this as a skin care product? Can it be applied topically to special areas of skin…or is there some systemic reaction that gives rise to the the dermatitis as a secondary action.
At present the pharmacology of the Kava does not seem well defined. If you want to get high on modulation of your GABA-a regulated chloride channels and inhibition of cytochrome p450…and shed your skin at the same time…
Be mellow…go for it.
It is interesting that our Denisovan relatives had a likening for this…(well have you ever watched a serious Rugby game?). ….you might want to know everyone is calm and peaceful before sitting down to dinner. I don’t suggest passing out too much alcohol. FA.
Comment includes all due respect.