Time to destroy another kava myth

[Palmetto]

Questions and a comment:

What is the basis for your statement that "headier" kavalactones extract more easily than "heavy" ones? In what solvent?

I use the USP HPLC method, Dr. Schmidt uses the Meissner method, Fiji uses Institute of Applied Sciences, some USA labs have used the INA method, and Dr. Lebot uses an HPTLC method of his own design. Clearly this needs to be standardized, but the discrepancy between these methods is not as large as one might imagine. The total KL percentage is actually the largest variance (due to differing extraction techniques), but aside from this the fundamentals of KL assay are the same between methods and reported chemotypes are quite close.

Extraction in all of these methods is certainly more efficient than traditional water prep, but they still provide a benchmark for comparison. The goal is not to extract the same amount of kavalactones as water prep, but rather the same proportions.

It is also important to remember that chemotype alone is not a very precise means of describing a sample of kava. A minuscule change between kavalactones changes their order in the chemotype, and adjacent kavalactones could be very close to equal in content or widely separated. Chemotype was never meant to be used as we do, it's much more useful to compare individual KL percentages.

Deleted User,

I'm not attacking you. Please don't view it as such.

There have been several papers mentioned previously by me and others on this board that stated that the proportion of kavain to other KLS is higher in water prep than in acetone, ethanol, and hexane fractions. Usually, but not always, this means that kavain is more polar, and that more efficient extraction methods will change the proportion of kavalactones compared to each other, as reported in those papers.

 

[Rick.Sanchez]

Deleted User,

I'm not attacking you. Please don't view it as such.

There have been several papers mentioned previously by me and others on this board that stated that the proportion of kavain to other KLS is higher in water prep than in acetone, ethanol, and hexane fractions. Usually, but not always, this means that kavain is more polar, and that more efficient extraction methods will change the proportion of kavalactones compared to each other, as reported in those papers.

That doesn't make any sense. Kavain is the least polar kavalactone

 

[HeadHodge]

I'm really enjoying this conversation, but could you guys quote some sources for your info once in a while so I can follow along?
Like for example: Why is it believed that Kavain is the least polar kavalactone?

 

[Kojo Douglas]

@Deleted User has clarified that his work was on hiatus due to personal reasons. We all know that. I wish we could move on from these tenuous topics and be positive towards each other. My point was that I don't really get too excited about the science behind Kava, and really just enjoy drinking it.

Bula to Deleted User, Bula to all who put effort into Kava.

 

[Rick.Sanchez]

I'm really enjoying this conversation, but could you guys quote some sources for your info once in a while so I can follow along?
Like for example: Why is it believed that Kavain is the least polar kavalactone?

If you just look at the structure of kavalactones, you'll see that kavain and it's hydrogenated analogues have fewer polar functional groups, and they're mostly aromatic hydrocarbons. The other kavalactones have more polar functional groups, so they're more polar molecules.

A basic way of thinking about polarity is that it has to do with differences in electron affinities of different molecules. If you have a large difference in electron affinity between covalently bonded atoms, then you will have polarity

A rule of thumb is that like dissolves like, so a polar solute is going to dissolve better in a polar solvent.

This a simplification of something that can be pretty math intensive to describe, but a trained eye can easily spot differences in polarity without using computational programs

 

[HeadHodge]

If you just look at the structure of kavalactones, you'll see that kavain and it's hydrogenated analogues have fewer polar functional groups, and they're mostly aromatic hydrocarbons. The other kavalactones have more polar functional groups, so they're more polar molecules.

A basic way of thinking about polarity is that it has to do with differences in electron affinities of different molecules. If you have a large difference in electron affinity between covalently bonded atoms, then you will have polarity

A rule of thumb is that like dissolves like, so a polar solute is going to dissolve better in a polar solvent.

This a simplification of something that can be pretty math intensive to describe, but a trained eye can easily spot differences in polarity without using computational programs

Thanks. I have a little electronics background, which involves molecular polarity on a basic level. So I follow that and thank you for your explanation. Regrettably the chemistry part is my failing except when it comes to making battery solutions with lead and acid.

 

[Rick.Sanchez]

Thanks. I have a little electronics background, which involves molecular polarity on a basic level. So I follow that and thank you for your explanation. Regrettably the chemistry part is my failing except when it comes to making battery solutions with lead and acid.

Thats neat. I personally was always more of fan of chemistry than physics. I imagine physics is more relevant to electronics.

Edit: @HeadHodge what kind of work with electronics have you done? Just curious : )

 

[HeadHodge]

Thats neat. I personally was always more of fan of chemistry than physics. I imagine physics is more relevant to electronics.

Edit: @HeadHodge what kind of work with electronics have you done? Just curious : )

In the Air Force I was a PMEL (precision measurement equipment laboratory specialist). A glorified title for saying I calibrated and repaired military test equipment.

Then I used the G.I. Bill to get a degree in Electronics Engineering and did a range of things from repairing TV's to micro processor projects at Tektronix in Beaverton OR.

I found electronics very interesting in theory but very boring in my real jobs. While working on microprocessors at Tektronix, I fell in love with software engineering and switched to that field for the rest of my life.

I think if I could do it all over again, I would probably be very interested in micro biology because I've come to realize your body is just one big complicated computer made from organic material instead of silicon.

 

[Palmetto]

@Rick.Sanchez I'll eventually look up some sources I quoted in the past. Polarity is not all about functional groups. It's as much about the location of those bonds. Some flourocarbons are often among the most nonpolar molecules, despite the fact that flourine-carbon bonds are polar in the right structure. I'm basing my thoughts on the fact that the proportion of kavain : DHK + DHM is higher in water extract than in ethanol, acetone, or hexane.

This isn't the exact paper I was thinking of, but it shows different KL extraction efficiencies for different solvents. Unfortunately, it doesn't compare water against the organic solvents.
"Kavalactone content and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of kavalactones using different solvents."
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4325077/pdf/13197_2013_Article_1047.pdf

This other paper discusses related issues of extraction but doesn't directly answer the question either:
https://www.researchgate.net/public...s_for_extracting_kava_lactones_from_kava_root

 

[Rick.Sanchez]

@Rick.Sanchez I'll eventually look up some sources I quoted in the past. Polarity is not all about functional groups. It's as much about the location of those bonds. Some flourocarbons are often among the most nonpolar molecules, despite the fact that flourine-carbon bonds are polar in the right structure. I'm basing my thoughts on the fact that the proportion of kavain : DHK + DHM is higher in water extract than in ethanol, acetone, or hexane.

This isn't the exact paper I was thinking of, but it shows different KL extraction efficiencies for different solvents. Unfortunately, it doesn't compare water against the organic solvents.
"Kavalactone content and chemotype of kava beverages prepared from roots and rhizomes of Isa and Mahakea varieties and extraction efficiency of kavalactones using different solvents."
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4325077/pdf/13197_2013_Article_1047.pdf

This other paper discusses related issues of extraction but doesn't directly answer the question either:
https://www.researchgate.net/public...s_for_extracting_kava_lactones_from_kava_root

Yes it also had to do with the geometry of the bonds. I was trying to give a very basic explanation. That said, even if you have a molecule that is nonpolar overall, it can still have local differences in electron density and electrostatic potential.

There are several electronegative scales, and the best one for quantification based on the concept of electronegativity is the Alfred-Rochow scale (I think that's the name. Don't remember for sure off the top of my head). The explanation for electronegativity is an inverse relationship between the effective nuclear charge and the radius of the nucleus to the valence electrons. In simpler terms, electronegativity depends on the charge of an atom and how far that atom is from the electrons that it shares in its covalent bond. A more common electronegativity scale is the Pauling scale which is more empirical, but they both agree quite well most of the time.

So, when I look at the kavalactones, I see a greater ratio of polar bonds to nonpolar bonds in methysticin and yangonin analogues than kavain analogues. I'm also considering the geometry of bonds, but even if the geometries cancelled out the polar bonds, the bonds would still be polar because atoms with different electronegativities will always share electrons in proportion to their difference in electronegativity. Like I said before, a trained eye can pretty easily see differences in polarity when youve spent hours every day starting at Lewis structures

Now solubility is dependent on intermolecular interactions which is more complicated than polarity alone. There are conjugated electron systems and aromatic rings, so pi stacking is another phenomenon to consider, but im not going to get into that unless someone wants me to explain more on it.

I skimmed the papers, and they actually agree more with what @Deleted User said. There are many many possibilities for why kavain was extracted in higher concentrations than other kavalactones, and one of those possibilities is not because kavain is more polar. Honestly, I think they're polarities are similar enough that I doubt their solubilities will be too different, and that would agree with the fact that different solvents extract very similar ratios of the different kavalactones.

Also wanted to mention that I'm kind of a science nerd and I like talking about sciency stuff. Im sure a lot of people don't care, but I hope I can provide some information for those who are interested in the biochemistry, and anyone can feel free to dispute my thoughts. Hopefully we can disagree but still down a few shells without having any bad blood

 

[Rick.Sanchez]

In the Air Force I was a PMEL (precision measurement equipment laboratory specialist). A glorified title for saying I calibrated and repaired military test equipment.

Then I used the G.I. Bill to get a degree in Electronics Engineering and did a range of things from repairing TV's to micro processor projects at Tektronix in Beaverton OR.

I found electronics very interesting in theory but very boring in my real jobs. While working on microprocessors at Tektronix, I fell in love with software engineering and switched to that field for the rest of my life.

I think if I could do it all over again, I would probably be very interested in micro biology because I've come to realize your body is just one big complicated computer made from organic material instead of silicon.

I share the exact sentiment on biology! I started out as a chemistry major and I was leaning more towards catalysis and chemical engineering. I got involved doing research in a biochemistry lab my first year of undergrad, and I absolutely loved it. I switched to biochem because it's truly amazing that life is essentially one giant biochemical reactor, and I feel like biochemistry explains life at its most fundamental level. I've since gravitated towards biomedical research.

That's cool that you lived in Oregon! I lived there for awhile and passed through Beaverton numerous times. Beautiful state.

 

[Palmetto]

@Rick.Sanchez no bad blood intended. Just a little debate. One of the papers I listed in this thread showed that yangonin and desmethoxyyangonin to have higher extraction ratios relative to overall kavalactone extraction with the most nonpolar solvents.

The thing I am intrigued by is that certain extraction methods produce headier or heavier than others with the same root batch. Since supposedly chemical alteration is not the major culprit, so the papers suggest, solubility seems to be the key, as we all seem to agree. But acidification has been partially implicated as well, but more in the fresh vs. not so fresh or heated realm. (forgot the reference)

 

[Rick.Sanchez]

@Rick.Sanchez no bad blood intended. Just a little debate. One of the papers I listed in this thread showed that yangonin and desmethoxyyangonin to have higher extraction ratios relative to overall kavalactone extraction with the most nonpolar solvents.

The thing I am intrigued by is that certain extraction methods produce headier or heavier than others with the same root batch. Since supposedly chemical alteration is not the major culprit, so the papers suggest, solubility seems to be the key, as we all seem to agree. But acidification has been partially implicated as well, but more in the fresh vs. not so fresh or heated realm. (forgot the reference)

I feel like solubility data should be somewhere.

Its more likely to be related to the content of the different kavalactones in the root... if you extracted more of a particular kavalactone, the most obvious explanation is that the root had more of that kavalactone or that particular kavalactone was physically more accessible

 

[ElDudarino]

Just to point out that you are assuming the 15% holds true for 2nd and 3rd wash. Since this seems like the kind of thing that is subject to diminishing returns - that is it's easier to get 15% on the first was than 15% of what's left on the second wash. The second wash might only extract 5% of what's left.

The CTAHR method specifically tests chips of kava, not powder, but most of the data is still relevant. They do not use an emulsifier, such as milk, lecithin, or coconut milk. Because the kavalactones are sparingly soluble or remain temporarily suspended in water, an emulsifier greatly aids in keeping the oily substances "mixed" in the water, much like vinegar helps suspend oil in salad dressing. Acetic acid in vinegar is an emulsifier. But also remember, if only 15% of the kavalactones come into the water at warm temps (at best), then second and third washes should be almost as strong as first washes, but experience shows that this is not quite as the math would suggest.

1st wash = 15% KLs
2nd wash = 15% * (0.85) = 12.7% KLs
3rd wash = 15% * (0.85) * (0.85) = 10.8%

Part of this is because many of the particles pass through the filter and are swallowed whole, similar to micronized powder.

 

[Palmetto]

Dragging up an old thread, but ElDudarino brings up a valid point to an extent. My previous calculation was a crude approximation, but if the quantities of kavalactones in the fibers were much greater than the amount released into water for each wash, then it would actually be a sigmoidal curve of kavalactone release to water over time. In other words, until the kavalactone levels got depleted to a point where the release each wash had a significant effect on the amount of kavalactones left, there would be an initial plateau of similar amounts of kavalactones released for a while, until there would be a rapid drop per wash. Then after most of the KLs had been released, there the levels of KLs released would be low per wash and slowly decline. I will assume that is what @ElDudarino meant. My earlier post was more simplistic, because most people don't wash their kava too many times.

 

[aslaause]

I wonder what makes an Aluball work? I know from experience that traditional prep makes for stronger kava but the Aluball isn't too bad.
install vidmate get-mobdroapk.com

 

[Groggy]

I wonder what makes an Aluball work? I know from experience that traditional prep makes for stronger kava but the Aluball isn't too bad.

The simple mechanics of agitation is all there is to the preparation method. The water moves back, forth and through the ball containing the root powder, and as you shake you extract the lactones just as you would from kneading. Given the limited size of the product, you get a weaker beverage compared to a traditional prep.