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Author: Subject: Capsaicin extraction and isolation
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Capsaicin extraction and isolation

 Quote: from Wikipedia: The chemical compound capsaicin (C18H27NO3) (8-methyl-N-vanillyl-6-nonenamide) is the active component of chile peppers (Capsicum). It is an irritant for mammals including humans and produces a sensation of burning in the mouth. Capsaicin and several related compounds are called capsaicinoids and are produced as a secondary metabolite by certain plants of the genus Capsicum (chile peppers), probably as deterrants against herbivores. Pure capsaicin is a lipophilic colorless odorless crystalline to waxy compound.

Some of the properties of this compound include a molecular mass of 305.41 g/mol and a melting point of 62 - 65°C. I'm not sure of solubilities of this compound but believe that is it soluble in ethanol and in oils. I want to try an extraction. Basically I believe that I can reflux dried red pepper seeds in ethanol and filter in filter paper while hot. The filtrate I can boil down and crash with water (assuming capsaicum is insoluble in water) to recover the waxy crystals of capsaicin.

Does this method seem like it would work? Any suggestions?

The_Davster
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I gave it a shot a few weeks back using only 2 really hot homegrown chillies. Used acetone and ground dried hot pepper in acetone, mag stirring for 8h. I got a bright red solution which I filtered of pepper parts and left the acetone to evaporate. I was left with a small ammount of red ooze in the bottom of the beaker. Seeing as there was so little of it I decided to flush it, and while I was washing the beaker a small particle must have become airborne which I preceeded to breathe in. YOWEE

Be carefull

I plan on growing some Red Savina this summer so I can give capsaicin extraction another try. Ideally I want to end up with a white crystalline product.

http://www.rowan.edu/biology/faculty/obrien/GBPP.Hot%20Peppe...

The hard part is separating the capsaicin from the capsiacinoids

[Edited on 13-2-2006 by rogue chemist]

BromicAcid
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There is one nitrogen atom there that might help to facilitate an acid/base type reaction. I was personally thinking about doing the same extraction by coincidence a few weeks ago, I like my food hot and the food suppliers that sell "Pure Cap" charge quite large sums of money, I find it strange that the brand "Pure Cap" has a scoville rating of only 500,000 (I say 'only' as a relative comparison) the hottest sauce that I was able to find has a rating of 16,000,000 Here is a good site:

http://www.sweatnspice.com/hottest_sauces.php

So yeah, extracting my own capsaicin could save me $considering the hottest sauces sell for over$200 for small amounts.

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12AX7
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Considering an Habanero is around 250k Scovilles, you'll need to concentrate it roughly 100x, i.e., 1% yield at best. Which I suppose isn't bad in regards to plant yields, depending on your point of view.

If you've been cooking much (surely you have! ), you'll note the heat always concentrates in the fat. I'd go for a lipophilic solvent; paint thinner (mineral spirits) might work nicely if you don't intend on eating it (I should hope not, at that strength ). That might evaporate a bit slowly, so heck, alcohol or acetone probably work fine. How about say, ether, ordinary or petroleum type?

And you're right, an alkaloid extraction might well do something. Seems to me with all the hydrocarbon hanging off, you'd end up with something like a fricking spicy detergent, though!

Tim

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The_Davster
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I want some capsaicin for cooking purposes as well, so as non-toxic a method as possible is of course. I plan on starting with a large number of peppers and doing the extraction with some everclear or the most concentrated drinking grade alcohol possible to get the red oil of capsaicin and capsaicinoids, for most cooking purposes the oil is likely fine, or perhaps better as each capsaicinoid has its own type of burn, so a mix would give a much nicer, broader burn.

Separating them via acid/base extraction I would think would be complicated by the fact that it is an amide nitrogen and too much/too hot base could break up the amide bond. I have no experiance with the acid/base extraction of amides(only ever done amines), so I might be rambling....

Kind of off topic but...

 Quote: Maybe rogue chemist has fondness for cajun food , three alarm chili , and slices onions with a smile You know the sort that eats hot peppers like they were celery sticks , peppers which would be lethal to the average person

Now how did rosco predict my fondness for spicy food before I ever acquired a tase for them....

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 Quote: Originally posted by BromicAcid ... the hottest sauce that I was able to find has a rating of 16,000,000

What's weird is that from my source, pure capsaicin has a rating of 16 million Scoville units (it wasn't a sauce)
BromicAcid
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Hence why sauce was in ittalics. It was crystals of the pure capsaicin but it is sold on that hot sauce site. Pure capsaicin is scary, a crystal on the skin supposedly causes destructive damage, I couldn't imagine what a crystal in the mouth would be like. Scary like boiling drain cleaner scary, right up my alley.

[Edited on 2/13/2006 by BromicAcid]

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innervision
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I would love to have pure capsaicin, but even if there is an easy method of extracting it, I don't think I would do it... Not without an astronaut suit. It will blister your skin on contact and can stop breathing. Nasty stuff.

I did however, make a very strong habanero oil:

I chopped 1lb. of orange habs into small peices and dehydrated in an oven on the lowest setting.
I then crumbled them up into a powder, placed into a 400mL beaker and topped it off with isopropanol.
Then I gave it a mad stirring, let it sit, followed by another mad stirring.
I poured the now orangeish liquid through a coffee filter to yield a very nice looking bright orange liquid.
I placed the beaker on a hot plate and evaporated most of it, then using an eyedropper I filled up a ~1mL vial with the concentrated dark red solution and placed it onto the hotplate.
Everytime the vial had more room I would add more drops of the dark red capsaicinoid solution into it to top it off.
I did this until all the liquid from the 400mL beaker was gone.
My yield was about (i'm guessing here) 0.5mL of very dark red, very thick oil that hardens in the fridge.

This stuff is unbelievably hot! I dip the very end of a toothpick into the surface of the oil (nowhere near a drop's worth) and it will heat up my entire mouth and my ears will tingle and i'll be suffering nicely

I have some Pure-Cap and I can honestly say that it is like tap water compared to this stuff I made.
innervision
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Here are some pics displaying its viscosity. I store it in the fridge, and when it warms up becomes a viscous oil, as you can see in the "Upside down with drip."

Chris The Great
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 Quote: Originally posted by BromicAcid Scary like boiling drain cleaner scary, right up my alley.

Well I'm sure that would spice up your food as well, and be far cheaper. Other alternatives could be lewisite (mustard gas wouldn't work, since you'd eat the food and only get the 'spicy' until a few hours later). Perhaps an application of tear gas would spice it up (anyone tasted chloropicrin?).

On a more on topic note, pepper spray should yield large amounts of the desired chemical with a simple extraction. Might be cheaper than a crate of super-hot peppers. From what I've seen it is up to 10% capsaicin depending on the brand.
unionised
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Since the nitorgen in capsaicin is in an amide I think it won't be very basic. By the time you have a strong enough acid to protonate it, hydrolysis will set in.
I think a major part of the problem with purification would be removing the fats from the extract. If I wanted to do this I might try chromatography.
chemoleo
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There's a presentation I once did on a variety of 'taste' receptors, which included capsaicin, whose action is sensed by heat receptors. Essentially, capsaicin mimics the action of heat, similar to menthol mimicking the action of cold.

Attached are excerpts of that presentation. It's also got the original reference (some nature paper), where the extraction of capsaicin is described. If you want I can dig out that paper at a later time.

Attachment: capsaicin.pdf (427kB)

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Flip
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Oleoresin capsaicin

I remember hearing from a salesman that the hottest peppers you can find will still only be in the range of 5000 Scoville units... police strength pepper spray on the other hand is around 2,000,000 Scoville heat units. I'm not sure if the oleoresin is what you're after, but this might be a source.
Ramiel
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Perhaps a little light can be shed on extraction with he following anecdote:
Probably the most pain I've been in <i>in my life</i> apart from shattering a bone into pieces (just to give you a reference) was from eating some leftover Chinese food. It was a "chilli & tomato omelette" (obviously with some rice) dish which had been made in the morning and left to sit in it's oily putrescence under heat-lamps in a little plastic container for hours on end. The omelette was fine, just a little bit of hot coming from the dried chillies (~ 5-7 cm long, deep red - very common I think) - countered pleasantly with the sweet tomato. I got to the bottom and saw that after finishing all the rice and then omlette, a single red chilli had escaped, along with a puddle of oil (I assume vegetable oil of the cheapest brand)... given how much I enjoyed the meal and not thinking too much about the chemistry of what I was doing, i scoffed the whole lot down... started chewing...

Let me relate to you the sensations for science’s [read:humour’s] sake, and to demonstrate how I come to my conclusion?
Okay; Immediately, a pleasant warm sensation: thinking "wow, that's nice and hot"... "Yea, really hot, I wonder if I can actually finish this? Better start to chew it up! " *chew* *chew* *chew*... at this point the subject realises that something is amiss, the eyes start to water, mouth starts to burn, the skin on my head starts to crawl, the <i>outside</i> of my face and lips start to burn… 5 seconds later, salivary glands go hawire, cough and gag reflex starts to kick in, eyes watering too badly to see five yards ahead. Subject spits out the offending matter – too late, mouth is burning with an industrial quality, very acrid and blistering sensation, breathing becomes laboured wheezing amongst coughs… I stumble to the nearest toilet and vomit (I hope we are all being scientific at this time and not smirking!). This goes on for a good five minutes while the subject consumes litres of water and gargles desperately with any chemically active mouthwash/foodstuff he can think of. Pain. Agony!
I realised that at the end of the ordeal (and I have come to call it that) that I was crying, not out of any tearing reflex, but out of pain, hatred and self pity. I’m not a big cryer, having cried perhaps 5 times in my adult life… this was certainly one of them.

So I concluded that most of the capsaicin from all of the chillies was extracted in the organic vegetable oil, due to the mild nature of the eaten chillies (with seeds) and the contrasting EVIL of the oil vis uneaten chilli (or “Rambo chilli” as I have come to call him). Recall that they were simply cooked in oil, then put in a closed container with heat (kept above 60*C as per hygiene regulations) for 4-7 hours. I should like to repeat the experiment under controlled conditions tonight, and will get back to you, since vegetable oil is a food friendly solvent. I suppose we’ll all know by tomorrow whether I’m just a pansy, a <i>silk shirted sissy</i>, or a simple idiot.
Thankyouforyourtime
Ramiel

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I vote for sissy .
I remember a friend who ate a whole chile from some unknown Mexican plant in his front yard. He dropped to his knees, claiming he could barely breathe. A while later (after more chiles eaten) he ate one without too much fuss. He did have to go get water though.

Back then I could barely eat a tiny chunk of a habanero, but now I can pop one in my mouth and chew it to a fine consistency and swallow without too much of a spectacle, and no water until the burning stops.

I think you're just not used to capsaicinoids yet. The oil in your mouth surely didn't help, but give it time and practice...
Ramiel
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Naw, I conducted the "extraction" with a few different oils.. one was a cheap as chips "sunola" oil (which I suspect the resteraunt to have used), then olive oil, then plain "black and gold vegetable oil" (okay, so I'm a cheap student). The sunola oil <i>seemed</i> to work the best. After heating some chopped chillies in the oven (closed container) for a few hours, the sunola was clearly the spiciest of the oils, while all of them definitely had a little warmth in them.

My father is a sadist, he dared me to eat a tablespoon of tobasco when I was a wee three years old. From this harsh upbringing, I have learnt to love chillies, and am rarely bothered by them, but what really shocked me regarding the above experience were the <i>involuntary</i> physiological responses.

I suspect that if you heated the sunola oil/chopped chilli mix you’d get a very favourable extraction of capsaicin in an edible medium.

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kazaa81
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Some capsaicin data...

Here is some capsaicin data, from Handbook of Chemistry and Physics 85th edition.

Capsaicin

C18H27NO3
CAS #: 404-86-4
Mol. 305.412 g/mol
Form: monoclinic plates or scales (from petroleum ether)
M.P. 65°C
B.P. 215^0.01°C
Insoluble in H2O;
very soluble in EtOH;
soluble in diethyl ether, benzene, petroleum ether;
slightly soluble in concentrated HCl;

innervision
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Lol. When I was three, I don't think I knew what a dare even was!

Extraction with oils would only work for food, and it would only be medium spicy. (Don't get me wrong - I'm comparing it to the IPA extraction I did).

I too am a sucker for those involuntary physiological responses. I start to hiccup like crazy, then my eyes start dripping like a faucet. Even when it's not too hot.
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In response to kazaa81, If one were to distill cheap wodka something in the region of 80% EtOH and (pretty much) 20% water would be obtained. Grind the chiles, put them in the "wodka" under gentle reflux with good stirring for a few hours, filter and then crash in icecold water. That should precipitate a lot of the capsaicin right?

[Edited on Wed/Mar/2006 by Nerro]
innervision
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Wrong. There definately would be capsaicin in it, but chiles have many capsaicinoids that are alcohol soluble. Which capsaicinoids and in what ratio depends on what type of chile you're using. There also would be other oils from the chiles that might crash out too. You wouldn't end up with a crystalline capsacin product.
Nerro
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I meant dried chiles, and if it's for food purposes that means you want all the capsainoids.

[Edited on Thu/Mar/2006 by Nerro]
lordmagnus
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I remember watching something on TV about Capsaician extraction, the absolute pure kind is a fluffy white powder, they have to wear overpressure suits (think the nuclear reactor scene in James Bond "Docotor NO"). The pure stuf can be like nerve gas, and kill with just a few flakes, this is diluted down and made into those topical pain medications, although I think spraying MACE onthe injury would be cheaper and just as effective.

I\'ll kill a man in a fair fight, or if I think he is gonna start a fair fight, or if he\'s bothrn me allot, or if I am getin payed good, or probably over a good woman.

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innervision
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 Quote: I meant dried chiles, and if it's for food purposes that means you want all the capsainoids.

Soaking dried chiles in alcohol won't give pure capsaicinoids + alcohol.

If it's for food, then why would you want crystals. Trying to kill someone? For food, you would have to redissolve them in a LOT of something, so why even go as far as to obtain crystals? Not even the most chile-tolerant person on the planet could take a sprinkle of capsaicin on his food.

I did try the crashing in ice water thing with saturated IPA. The water just turned orange/brown.
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A long long time ago on USENET the subject of capsaicin came up. According to a neurobiologist who posted, capsaicin is a neurotoxin. It first irritates the substance P neurons, causing pain. More of it disables the neurons, causing "tolerance" of capsaicin. Most of the time, the neurons regrow or recover, causing the loss of tolerance. The disabling of pain neurons is the behavior exploited in the capsaicin pain cream. Very potent stuff!

A possible food-grade extraction process would be to grind chiles in food-grade vegetable oil or (gasp!) lard, then extract the oil with more volatile solvents. The pigments in the chiles are less soluble in oil than the capsaicin.
lordmagnus
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Actually Capsaicin interfeers with the P-substance in neurons that transmit pain, but like I was saying in a previous reply, the absolutly pure stuff is handeled in the overpressure suits to protect the workers, it's like nerve gas at that purity..

I\'ll kill a man in a fair fight, or if I think he is gonna start a fair fight, or if he\'s bothrn me allot, or if I am getin payed good, or probably over a good woman.

-Jayne Cobb (Serenity)

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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   » Detritus   » Test Forum