Piperine Extraction from Black Pepper

In this video I extract the chemical piperine from black pepper, which is the chemical responsible for the unique flavor and aroma of peppercorns.
I used pre-ground pepper here and I suspect that has something to do with my relatively low yield. Might try this one again with actual peppercorns and see how it goes.
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[@hoggif]

Depending on speed of boiling, three cycles of extraction may not be very much. You may want to try long soaking time (slow boiiling) and/or more cycles.

[@TheZombieSaints]

I was going to say the same thing. I've done this exact extraction and my group decided to let it cycle for 2 hours and the solvent eventually would come through clear, I think we got like 70% of the piperine out.

[@MrCrazyChemist]

You can make thimbles by rolling up a sheet of paper in a cylinder and stapling the bottom shut. It's a bit less hassle than the cotton and helps the siphon work better when using fine powders. Another tip I use is filling the boiling flask by pouring the solvent over the soxhlet, saves time on a couple cycles Keep up the good content!

[@tfwmemedumpster]

piperine degrades over time and obviously faster in pre ground peppercorns. so ideally you should use whole peppercorns and grate them shortly before use. that would certaintly increase yield. also preground peppercorns are usually lower grade stuff since you can't tell by looking at them. This is true of most spices, the pre ground or pre extracted version is usually low[er] grade stuff that can't be sold whole

[@integral_chemistry]

Yeah I definitely want to try again with an equal mass of some very fresh peppercorns, think it would be a fun little proof that the pre-ground stuff is trash.

[@tfwmemedumpster]

@@integral_chemistry tastebuds are usually sufficient for that. Even being old makes them weaker.

[@Gman193]

To improve yield, you could soak the pepper in you solvent before starting the extraction. This could even be done in the soxhlet. Just put your pepper in the soxhlet, cover with isopropanol ( just not enough to trigger the siphon) and leave it like that for a couple of days. Also you can crash out the piperine with you solvent warm and then let it cool down, that way you get bigger crystals and less wil pass through your filter. Other then that, nice video.

[@wbedard]

Really enjoying your content! I think it's the perfect length and level of detail for a chemistry-enthusiast (as opposed to professional...) audience. Keep up the great work!

[@integral_chemistry]

Thank you so much! I definitely make these through the lens of accessibility, I feel too long and you lose people, too much detail and you lose people, but overly dumbed-down and then it feels too much like pop-science. Glad you think I've got a good balance going on!

[@YoopDoop]

I actually love this, I am certainly following you

[@196Stefan2]

2:50 Another downside of this process is that the extracted matter in the round bottom flask is exposed to the boiling temperatur of the solvent for a longer period of time (in the case of iso-Propanol 82 °C). But this cannot be prevented, except you choose another solvent with a lower boiling point (if there is one).

[@integral_chemistry]

I was actually thinking of doing this again with diethyl ether. Boiling point is 35°C and it forms a seperate layer in solution so I could do an actual washing step with the Extract

[@DangerousLab]

From my experience, using a thimble is counter productive since you can use less black pepper overall, I personally like to use cotton ball or "tea-bag" filter to contain the material for extraction, this not only increase the product, it is also much easier to clean than the timble, especially for extraction like capsaicinoid which the chilli stinks the fritted glass pretty heavily.

[@integral_chemistry]

I honestly agree with you (tbh I mentioned the thimble to avoid people trying to call me out for not using one lol). But yeah the thimble just feels too limiting. It sucks for all the reasons you mentioned and I'm not sure if my thimble is just the wrong size but I nearly had some overflow of particulate when I last tried to use it.

[@DangerousLab]

@@integral_chemistry Also when I am inserting the thimble, it slides on the bottom of the Soxhlet chamber pretty harshly, making a "clink" sound by hitting the glass, not sure if it will eventually crack it over multiple uses.

[@zuthalsoraniz6764]

Maybe you could try extracting allicin from crushed garlic? Haven't seen anyone do that one before on youtube, and it should be fairly well soluble in ethanol. Though it has a fairly short half-life at least in aqueous solution, which might make getting a decent yield quite tricky.

[@integral_chemistry]

That would actually be really cool! Do you know anything about its stability in organic solutions? Definitely would be a cool one.

[@snowy_owl3078]

Gj on the piperine extraction! Maybe you can synthesise capscaicine/caffeine/taurine/adreanlin next?

[@EddieTheH]

_Adreanlin...?_ Was that what Rocky Balboa had? 😁

[@aSCrouton]

You should try chile peppers for capsaicin others have done it but they stop at the oil not the pure crystals. I believe you already have the needed solvents for the final wash

[@integral_chemistry]

I've considered that honestly. I figure the oils could be separated out with a glycerin-ether extraction, the issue is separating the carotenoids from the capsaicinoids as they have such similar solubilities..

[@aSCrouton]

hmm yeah. the carotenoids dont have a phenol group like capsaicin though right? could you exploit the solubilities through protonation and deprotonation then? maybe the carotenoid species are too diverse for that to work. idk. @@integral_chemistry

[@MattbyNature]

This is a preparation we did in our undergrad organic chemistry lab! And I remember the recrystallization being the hardest step.

[@iivarimokelainen]

My NileRed craving is cured!

[@ForgottenRebel77]

5:10 - the forbidden latte

[@robertbanks8870]

How about making capsaicin crystals? I don't think anyone else has done that yet on KZbin. Cool video, by the way. Nice job.

[@louwclaassens4988]

Nile Red isolated it from chilli peppers. But not pure

[@robertbanks8870]

@@louwclaassens4988 exactly, like I said nobody has made the crystals.

[@hoggif]

@@louwclaassens4988 There seems to be no easy method of purifying capsaicin. There are some publications on how to do it (at least one that I know of that seems to be referenced much) and it was quite laborous. The problem is the other inmpurities that you get with excract. For smaller amounts something like chromatography is always an option but for anything but small amounts, such a simple method is no longer an option.

[@EddieTheH]

​@@louwclaassens4988 It's quite stubborn to purify further and it'd make boring video since it's just column chromatography.

[@ronritekinamatigai]

AFAIK, capsaicin is more like wax, it does not produce good crystals

[@NiC.kChenNC]

This is awesome

[@shootingsolution0123]

nice work! thanks

[@experimental_chemistry]

Noice! 🙂 (My shortest comment on this channel so far... 😊)

[@integral_chemistry]

ha that is true (to be fair not much to say about such a straightfoward extraction). Always appreciate the feedback on the more experimental videos! :)

[@TheFulcrum2000]

Grind your black pepper first for improved yield.

[@Gin-toki]

Preground black pepper, definetly has less taste and fragrance than freshly ground black pepper. I'm guessing it's due to oxidation or breakdown of the piperine in the pepper? I would not be surprised if you would get a higher yild from freshly ground black pepper, also ground to a finer powder instead of the coarse material you used.

[@arjovenzia]

mmm, around the 5 minute mark... forbidden coffee... it does look good...

[@pro-tech4494]

That black pepper oil is valuable in ayurveda ! (Medicinal purposes)

[@clarabisson7299]

excited for new videos

[@wesdblack]

Oooo. No no. Needs a 'sock' for the soxhlet siphon

[@rafaelgcpp]

Do some Limonene extraction!

[@integral_chemistry]

I actually did a video on that a month ago, but then I felt the video was too short and proceeded to extract citric acid and cellulose from the lemons and now the video feels too long... I'll probably just post it anyway tbh

[@rafaelgcpp]

@@integral_chemistry I suggested limonene as I always send limonene extractions videos to a friend of mine as a joke. She is a chemical engineer, but gave up after the first year working on a citrus oil extraction plant. She said she couldn't smell anything but oranges for hours after leaving the job. She went back to uni and graduated as software engineer and joined the company I work for. The orange extract trauma history is so funny when she tells, that I have to push her allindustrial processing of citrus I find!

[@Taranweb-hj3ez]

To extract the morphine alkaloids which solvent should be used? Ethanol or acetone or chloroform or ether? Or lime?

[@WaffleStaffel]

I buy black peppercorns in bulk from the grocery store. In the last couple years, they have been completely flavorless. I suspect the oils are being extracted from them, and the spent husks are being sold. It wouldn't surprise me if pre-ground pepper is being treated the same way. Twice the money for the same product. There's a conspiracy to _de-caffeinate_ our pepper!

[@integral_chemistry]

it is honestly total trash. The yield I got from this was kinda disappointingly pathetic to the point I wasn't sure whether to post the video. Even under conservative estimates I should have gotten like 10x as much, and I know my method wasn't THAT bad

[@enlightenedhummingbird4764]

Dang. I hadn't considered this, but I bet you're right. Argh. This planet.

[@WaffleStaffel]

@@enlightenedhummingbird4764 I know, right? There's a whole market centered around spent vanilla beans. I actually came across a website selling the stuff. The spent pods are ground and mixed with glycerin and glucose and sold as "vanilla paste," and people pay top dollar for it thinking they're getting whole ground beans.

[@stretchstrange]

4:31 mmmm coffee. lets have a little taste

[@unknown-ql1fk]

Anyone know if the NaOH/IPA step would work with capsaicin extracted in the same way? I did this extraction with c. Reaper peppers and have like 500ml of red oil but i want to refine and crystalize the capsaicin if possible. btw i know its dangerous and no plan to eat it, its just a fun project

[@integral_chemistry]

I actually am working on that exact project rn and what worked for me was actually dissolving the oil in glycerin and then extracting out the capsaicin with diethyl ether. Capcasin isn't soluble in glycerin but all the fats and oils are, so all the capcasin gets extracted into the ether which forms a nice seperate layer. Only issue is the red carotenoids also get extracted with the capsaicin and I've got no idea how to seperate the two :(

[@michaelgreaves2375]

You need to go to a "fancy" restaurant (like olive garden) and have them grind the pepper at your table - right in to the Soxhlet extractor. Then, a nice dessert and espresso! Bon Ape-tit!

[@DeeegerD]

From the first second the real question was WHY?

[@RedDogForge]

what, if any, uses are there for piperine?

[@Hobypyrocom]

extract THC from weed 😜

[@integral_chemistry]

That could actually be a really cool vid.. I'd need to clear it with my actual place of employment first though 😅

[@pacman10182]

how do you spell then name of the extractor?

[@integral_chemistry]

Soxhlet

[@pacman10182]

@@integral_chemistry thanks, should probably be in the description

[@hattree]

You should get whole peppercorns and grind them finer.

[@EddieTheH]

Apparently, when ground too fine, pepper's a dick for getting past the cotton and blocking the syphon tube. I've seen more than a few people on forums, etc, who've lost soxhlets to it.

[@fluorone_red]

I think you run extraction for too short. At least 10 cycles seems ok. It is not unusual to left extractions run overnight.

[@integral_chemistry]

I do 100% agree. I usually always feel extraction times are overkill, but I think in this instance it would have possibly helped push the recovery to something less terrible. Definitely intend to do this again with fresh peppercorns to compare

[@jeremycrochtiere6317]

Black pepper avg around 4-10%

[@robclements4957]

Homemade insecticide

[@Moritz___]

Extract HCN from almonds xd But beware not to kill yourself

[@RedDogForge]

kratom alkaloids

[@djsnowman06]

Pure capsaicinoids

[@jogandsp]

Idk why you stop talking every time you show something cool. I promise we can look and hear at the same time

[@integral_chemistry]

lol fair. To be completely honest the reason I do it is because I record the audio before putting the video together and my narration only really covers the actual procedure. Bc of this I end up without enough voiceover to cover "dead space" when there's just a cool reaction happening.. The solution is to get a mic that works with my PC instead of my Rode lav-mic but the model I want is dumb expensive.

[@urdnal]

Taste it.

[@Meleeman011]

extract thca from weed next

[@integral_chemistry]

I'm actually looking into that, but still checking with KZbin to make sure that I'd never get in trouble for it

[@stevelibby3]

Have you tried putting the soxhlet under vacuum? Not only does it reduce the boiling point of the solvent, (which will preserve constituents in the materials), it greatly speeds up the process. Greetings from Maine 🧪🔬

[@integral_chemistry]

Huh I actually hadn't considered that! I'll have to give that a try next time I use it, especially since I hadn't considered using some high boiling solvents in it for that exact reason. Greetings from Massachusetts btw! I've been considering moving to Maine for years