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Author: Subject: Capsaicin extraction and isolation
densest
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There's also a crude but effective extraction procedure: vaporize the capsaicin at 220C in hot oil. Condense the vapors. The resulting goo is potent.
minordemocritus
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after entertaining the though of various uses for concentrated capsaicin, i learned of the lovely transdermal properties of dimethyl sulfoxide (DMSO). it turns out that since DMSO is only slightly polar, it dissolves capsaicin rather nicely, on the order of 15 (synthetic) to 19 (oleoresin USP liquid) g/100ml.

the only problem is knowing the full effects of a capsaicin/DMSO solution on a human, and LD50 per concentration and dose. i propose unethical testing on arbitrary bad people.
Swany
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I obtained 1 lb of habenaros for this expirement, to be similar to innervision's.

I plan on extracting with denat. EtOH. I belive it is denatured with 4% methanol, does this sound plausible?

This is great fun. Wear gloves while your chopping, guess who didn't... yeah. Me. I licked my thumb, and I was greeted with a warmth, and then I unconciously rubbed my nose and inhaled. Followning this was a rather painful burning sensation... I love this stuff.

If I am interpeting this correctly, they just popped it in the microwave at low power for a bit? Essentially? I could be (and probably am) totally wrong... either way. It would seem they are dealing with raw fruits though, and I will be using dried powdered.

DrP
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 Quote: Wear gloves while your chopping, guess who didn't...

Hmm... My friends house mate made a very powerfull curry. He went to the bathroom after chillie chopping and forgot to wash his hands before going...... AGONY apparently... lots of screaming and tears!!!.... Beware! It's not just the mouth that smarts when chillie juice is applied...
12AX7
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One time I chopped up a jalapeno and didn't wash my hands... after I ate I was scratching my nuts and a pleasant warmness was discovered.

Tim

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innervision
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I don't have sensitive enough fingers to need gloves, but I know some people that get burned at the stake from touching even jalapenos. Strange eh? I know capsaicinoids burn people's mouths differently, but the fingers?

Oh, and Swany, DON'T burn the habs in the oven. You will be choked out of the house, and the oil will have a distinct burned taste. I know it's tempting to smell something smoking right out of the oven, but you'll regret breathing smoking chiles.

It's kind of like putting chiles in a blender with a lid then taking the lid off, and inhaling over the mouth of the blender jar, deeply.

The microwave article eludes me. I don't have access to that database.
Swany
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No, it not my hands that were burning, rather, every mucus membrane that they touched. I used the lowest setting, then mother graciously donated her dehydrator to use. Currently they are sitting under denat. alch for the weekend, as I am out of town.

innervision
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Lol. That reminds me of a story. I made some friends some rolls on the same cookie sheets I dried the habs on. The bottom of those rolls just about burned their mouths off. I even washed the cookie sheet pretty well, I thought.

Don't be surprised when you mom eats some flamin' hot dried apples some day soon.
The_Davster
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I recieved and planted my seeds for Red savina habenero and hotazel chillis. I also bought little plants locally of cayenne, thai dragon, and super chilli. A couple of them are known for 'prolific production' so by the end of the summer I should have lots of chillis

And of course after that will follow some sort of massive capsaicin extraction experiment.

And of course I will make some pretty potent chilli

EDIT: My fingers were burning just from handling the damp seeds

[Edited on 7-5-2006 by rogue chemist]

UniversalSolvent
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innervision's oil production looks like something I might want to try. Is it possible to substitute different peppers but use the same process, and obtain an oil of that pepper?

[Edited on 3-6-2006 by UniversalSolvent]
Ramiel
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One of my friends attempted to isolate capsaicin as well, it looked a lot like innervision's oil. Lost potency over about a year, but a fraction of a fraction of a drop still has a little warmth.

Could I reccomend some kind of chromatography to isolate the oils? Apparently, extraction with 95% ethanol saturated with sodium acetate at 60*C for 3 hours gets all the capsaicinoids out. Liquid chromatography with solvents "48.4% methanol, 30.2% HPLC grade water, 13.3% dioxane, 7.9% acetonitrile, 0.2% of 2% perchloric acid".<sup>[<a href="http://www.zarc.com/english/cap-stun/tech_info/oc/hplc.html">reference</a>]</sup> This seems to be fairly standard, with some alcohol (Me/Et/PrOH) and notably perchloric acid. I can't imagine what the perchloric acid does, but it seems universal in all such extractions.
"The first peak is the pigment peak, the second peak is capsaicin, the third peak is capsaicinoid.", pretty straight forward!

Column used was a low pore size silica column, 18% carbon. I could reccomend just using alumina!

P.S. <a href="http://en.wikipedia.org/wiki/Dorset_Naga">Hottest chillie in the world?</a>, "[people prefer to consume it by] touching the food with the pepper instead [of preparing it]." !

[re: rogue chemist, I only mentioned the exact elutant for posterity, I'm sure one could use any watered down alcohol mix... Not too sure what the perchloric acid does still - I guess protonating everything, but it couldn't hurt to include it.]

[Edited on 3-6-2006 by Ramiel]

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The_Davster
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Mmm dioxane and acetonitrile...tasty...

The ethanol/sodium acetate method seems quite interesting, if it extracts all the capsaicin, what percentage of the capsaicin does the usual ethanol extraction get out?

This is just my opinion, but other than a few articles and a link to the discoverer's homepage, which supposeldy sells the seeds(I couldent find them), there is not much on these peppers. I am not completly sure they actually exist. Mainly based on the fact that noone had any seeds they could sell me.

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Would steam distilltion be impossible?
The Boiling Point of Capsaicin is 210-220 degrees Centigrade so you would have to super heat the water i would think, making it a dry steam distilltion

Here is some stuff about it i find interesting http://www.chilliworld.com/chilli_FAQ.asp

Swany
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I thought it sublimes. I may attempt to purify my obtained capsaicinoids through this. I obtained the product described on the first page. My liquid was a dark red, however, his was oarnge. I think my extraction was more effecient, however.

I have found some important parts to making the extraction effecient;
1) Refux
2) Use a proper solvent, denat. alch works well if the denaturant is MeOH; 70% isopropyl isnt the best
3) Make sure the dried habenaros are a fine powder

denatured
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Breaking Down of Capsaicin

I'm addicted to pepper and chilis ... really .. I cannot eat anything unless it contains a considerable amount of capsaicin .... the problem is that I realized that it is seldom digested ! ... and that makes certain moments of my life bad ... very bad ....

Now ... anyone knows how capsaicin is treated by the body? or if there is something I could eat(or drink) that de-hotify it or de-activates it? of course I don't need to say that I'm human and strong mineral acids do devstate me ... thanks very much for reading this ... and one last thing ... you can delete this Polverone if you want after I get some responses ....

12AX7
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Not that I know of. Best bet is probably to genetically modify yourself along the lines of capsaicin-resistant birds.

Capsaicin is indigestible, which is why it burns coming out the other end. I suppose if you ate a lot of it, it would be comparable to eating mineral oil or wax, both indigestible fatty chemicals. You'd be dead, or at least hospitalized from sheer pain, after consuming enough capsaicin to appreciably change the composition of your feces (for example, the amount of mineral oil you would consume for a laxative).

Tim

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YT2095
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youll never escape the "Bum Burner" next day, no matter how much you adulterate the capsiacin and capsiacinoids, Some will be absorbed in lipids that enter the blood, but they non-the-less will be processed and excreted.
you will find over time the Calcium Ion pumps in the nerves will get saturated and itll no longer be too much of an issue, you need regular amounts of this in order maintain this status, unlike Virginity, it Does grow back over time

consider this, IF Capsiacin was incapable of being Digested, how come large amount can Kill You!?
it IS a Neuro-Toxin afterall

\"In a world full of wonders mankind has managed to invent boredom\" - Death
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12AX7
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 Quote: Originally posted by YT2095 consider this, IF Capsiacin was incapable of being Digested, how come large amount can Kill You!? it IS a Neuro-Toxin afterall

Ah true, I didn't know about neurotoxin.

But things *can* be absorbed without being digested (molecularly altered through the gut), so there

Tim

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unionised
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Any of it that gets absorbed is likely to be metabolised by hydrolysis of the amide group or oxidation of the methyl catechol. Some lipophilic materials are better absorbed in the presence of emulsified fats so creamed coffee might help by transfering the problem to your liver rather than err,... well you know where the problem is at the moment. I think the effect might not be very great.

Other materials responsible for the same "taste" like ginger or even ordinary pepper might hydrolyse more rapidly, or be otherwise degraded in the gut. Maybe you could try these and do the comparison.
What's the story with chili anyway? The poor plant spends millions of years eveolving to be practically inedible so even wild animals won't eat it; then some people put it in food.

EDIT
A bit of googling suggests that horsehadish might suit you well. Accoring to this, the pungency is lost in a matter of minutes.
http://www.uni-graz.at/~katzer/engl/Armo_rus.html

[Edited on 7-9-2006 by unionised]
YT2095
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Alylisothiocyanate (the active part in horse radish) gives a different kind of "hit" again, more of a nasal top of your head blown off, it requires no tasting of it. in fact being of the brassica family the taste and smell to a lesser degree iss the same as that of a cabbage heart.
I grow this also, and make a "Hot sauce" with a 50/50 combo of this and ground chili (White habanero) and left to mature in vinigar/salt mix for at least a year. Wow thats stuffs good, but when you open the jar, its essential not to breathe any of the gas, you Will drop the jar!

raw radish like Wasabi doesnt effect like chili on its way out though, so it depends on the type of hit you want?
Pepper will also burn on the way out.

\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
denatured
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"Not that I know of. Best bet is probably to genetically modify yourself along the lines of capsaicin-resistant birds."

yes , right..

"Capsaicin is indigestible, which is why it burns coming out the other end. I suppose if you ate a lot of it, it would be comparable to eating mineral oil or wax, both indigestible fatty chemicals. You'd be dead, or at least hospitalized from sheer pain, after consuming enough capsaicin to appreciably change the composition of your feces (for example, the amount of mineral oil you would consume for a laxative)."

I've been eating this stuff since I was 8 years old .. and here I'm .. posting on a forum 2006................

"you will find over time the Calcium Ion pumps in the nerves will get saturated and itll no longer be too much of an issue, you need regular amounts of this in order maintain this status"

What do you mean ? which issue ? getting rid of it or its effect becomes mild?

"What's the story with chili anyway? The poor plant spends millions of years eveolving to be practically inedible so even wild animals won't eat it; then some people put it in food."

Its story is simply that it gives the food the best taste ever, also it can help you cover badly cooked food by filling the food with a very hot sauce .. believe me .. whoever is gonna eat it .. won't think of how horribly you cook ...
Other thing that made me call it addiction is that I'm pretty sure that there is something goes in the brain after I eat it ... something pleasant ...

12AX7
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Quote:
Originally posted by alnokta
[quote fixed]
 Quote: I suppose if you ate a lot of it, it would be comparable to eating mineral oil or wax, both indigestible fatty chemicals. You'd be dead, or at least hospitalized from sheer pain, after consuming enough capsaicin to appreciably change the composition of your feces (for example, the amount of mineral oil you would consume for a laxative).

I've been eating this stuff since I was 8 years old .. and here I'm .. posting on a forum 2006................

Yes, but you haven't eaten say, ten grams of pure capsaicin at any time.

Quote:
 Quote: you will find over time the Calcium Ion pumps in the nerves will get saturated and itll no longer be too much of an issue, you need regular amounts of this in order maintain this status

What do you mean ? which issue ? getting rid of it or its effect becomes mild?

Seems he means the rear end issue. Desensitization.

Tim

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YT2095
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the rear end but mainly the Tongue also, in effect, the mechanism that allows that particular receptor for pain to react, it gets blocked, (Think Key and Lock scenario).
over time you will be able to tollerate greater amounts just to get the same effect, thats NOT to say there still isnt an LD50 for Capsiacin, there is, it just means youll be less likely to protest as you near this level

Alcohol is similar in this respect also, a resistance can be built up to it`s effects, non the less, it still remains Very toxic!

\"In a world full of wonders mankind has managed to invent boredom\" - Death
Twinkies don\'t have a shelf life. They have a half-life! -Caine (a friend of mine)
Elawr
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Capsiacin binds to pain receptors and at first stimulates them, thus the fire you feel in your oral mucosa, (and later on rectally) when you ingest some high-proof pepper. Being lipophilic, it doesn't wash off easily, although whole milk, (not skim) helps some. Ironically, capsiacin is used topically for arthritis pain. Pain receptors become inhibited by prolonged transdermal exposure to the substance. Its available OTC as a lotion here.

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ramarao
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orgANIC CHEMISTRY

 Quote: Originally posted by alnokta I'm addicted to pepper and chilis ... really .. I cannot eat anything unless it contains a considerable amount of capsaicin .... the problem is that I realized that it is seldom digested ! ... and that makes certain moments of my life bad ... very bad .... Now ... anyone knows how capsaicin is treated by the body? or if there is something I could eat(or drink) that de-hotify it or de-activates it? of course I don't need to say that I'm human and strong mineral acids do devstate me ... thanks very much for reading this ... and one last thing ... you can delete this Polverone if you want after I get some responses ....
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 Sciencemadness Discussion Board » Special topics » Biochemistry » Capsaicin extraction and isolation Select A Forum Fundamentals   » Chemistry in General   » Organic Chemistry   » Reagents and Apparatus Acquisition   » Beginnings   » Responsible Practices   » Miscellaneous   » The Wiki Special topics   » Technochemistry   » Energetic Materials   » Biochemistry   » Radiochemistry   » Computational Models and Techniques   » Prepublication Non-chemistry   » Forum Matters   » Legal and Societal Issues