piperine, piperidine, piperonyl and pepper

Guest · Wed May 18, 2005 10:54 am

Over the years a broad base of knowledge is building on alternatives to common methods, a very interesting, and frontrunner for this excitement is piperonyl.

Used by shulgin, often used with nitroethane to produce nitropropenes, and hence ketones, then amine transforamtions take place.

Considering a subtle push now moving away from the conventional terminal alkenes , such as isosafrole, and the peracetic methods, and also the wacker from safrole., and in search for the new hobbyiest pathway to many exciting phenethylamines,

We don't all live next to a essential oil supplier, but we all have access to PEPPER right?

Further more, being able to quickly extract 7-10% of piperine from pepper with ethanol, should start to raise a few eyebrows,

biobrew · Thu May 19, 2005 5:54 am

I have about 5L and another 3L of EtOH that has been sitting in about a kilo of pepper for almost a year now.......this thread/will rock. Lot's of rotovapping to do with my imaginary rotovap Crying or Very sad

I'm finally ready for some experiments....let's go Twisted Evil

nubee · Master Archiver

i like finding out interesting and applicable things to do Smile

Bumblebee · Sun May 22, 2005 1:52 am

there are still 5 kilo of black pepper sitting around in a Box since a year or so...

Extraction via soxleth extractor was done succesfully, and isolation of piperine also.
working with piperine sucks Wink

. It feels like it is burning holes to your skin if get some on it. I was so bored that i didn´t try anymore, and found another otc way for piperonol...

But it is worth a try since pepper is cheap bulk available and contains sometimes more than 12% piperine.

I found Black pepper is best for this.

from 7%-12% piperine were isolated from Black pepper (piper nigrum)
the white species is less sharp and only up to 5% piperine was isolated.

A good source may be Black pepper Oil, obtainable from fragrant/essential oil companys...

hey! Smile

there seem 100% of the bees want to know more according to that poll until now.

"Magna pars est profectus.
velle proficere"
"An important aspect of advancement.
involves the desire to advance."
that´s sooo right...

stooge · Sun May 22, 2005 2:39 am

i don't know - shouldn't a butan gas (a la honey bee extractor) extraction also work for Piperin? or at least to obtain black pepper oil? Would make the whole thing a lot easier ... I would try but i don't have the possibility/ability to test the product of this procedure after it's done, so i don't know if it's worth the while ...

I'd say it should work, but, uhm, i wouldn't bet on it, my knowledge on chem is more or less near (or below) zero ... Smile

any comments, ideas, what ever?

Bumblebee · Sun May 22, 2005 3:17 am

How much butane will you need to extract a kg of pepper? ethyl alcohol or IPA is cheap and you can extract with a 500ml soxleth 200g of pepper @ once.

you can put one liter in a 2l Round bottom flask and equip with a soxleth and reflux condenser, the pure ethanol will condense and wash the pepperoil continuously out of your ground pepper in this paper plug (don´t know how its called correctly Embarassed

)

think on how much butane is needed to extract resin of our lovely plants.
the advantage of the butane is, that it will not extract the chlorophyll etc from plants but dissolves the whole resin. and it evaporates off like hell so its just fine for making oil but it´s also flammable like hell! Twisted Evil

stooge · Sun May 22, 2005 2:11 pm

sure, you're right, of course, but if there was swim who wasn't fitted with soxlet apparatus and so on, the butan gas method may still be a possibility ... Smile

and, of course, you're right, too, with the amounts of gas needed ... no clue how much ... Sad

Maybe same like with weed? hmmm ...

Bumblebee · Sun May 22, 2005 9:33 pm

Just cook your black pepper (finely ground) in denaturated Alcohol (like EtOH+1%MEK . you can get it for around 4$ a liter or less...).
You should own a reflux condenser (any will fit, it functions well with a liebig-condenser)
reflux 500g of pepper 6-8 hours in your ethanol, filter the pepper off and save the black extract. rinse the Pepper with another 250-500 ml of EtOH to rinse off pepper oil clinging to the wet powder.
the roughly 1500ml extract is concentrated via destillation to a volume of 100ml or until pure oil. The Ethanol you distilled off can be used to extract another batch of Pepper.
then you can go on and isolate your piperine from the extract with KOH adn water addition

Star-light · Blacklight bulb

Bumblebee · Mon May 23, 2005 3:25 am

Oops, right.
I meant oleoresin of pepper...
pure piperine is available from some chemical suppliers too, but where i live piperine is a controlled substance!
Cleavage with acidic KmNO4 was not successful in my case and Dichromate was not tried...

hahas · Mon May 23, 2005 5:23 am

it isn't surprising that acidic KMnO4 didn't work. btw, this was originally done neutral (at the beginning, at least - the reaction liberates KOH)
http://www.sciencemadness.org/talk/viewthread.php?tid=3007&page=2
as was the preparation of aldehydes from propenylbenzenes.

the quoted percentages of piperine are exceptional for actual isolation, 3-5% yields are common in the lab. not all pepper is created equal, and perhaps the cheaper pepper contains less.

tonyxxy · Wed May 25, 2005 2:59 am

It seems there's very little information on this subject especially about piperic acid--->piperonal. However this route is 100% OTC. As we live in the year 2005 and there's a major cutdown on sassy containing oils I think it would be great for everyone to further investigate this route. Can't wait to see some results.

MargaretThatcher · Wed May 25, 2005 3:41 am

Looks like KOH and then CuSO4 is the best route. Problem is sheer volume of solvents required, whether water or not. This is not as practical as safrole routes. Then you need nitroethane to go with the piperonal, and that is definitely not OTC and also difficult to make.

Guest · Wed May 25, 2005 3:35 pm

MargaretThatcher,

I believe we will find our way and make this otc, with better research,

Something intersting I just found, said that piperidine can be preapared by the dry distillation of the hydrochloride of penta-
methylenediamine (Ladenburg, Ber., 1885, J#> 3101)-

That is certainly good news,
pentamethylenediamine is also called Cadaverine, which is made by the decarboxylation of our good frined Lysine,

Cadaverine is a foul-smelling polyamine produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine. Cadaverine is the decarboxylation product of the amino acid lysine.

MargaretThatcher · Wed May 25, 2005 8:26 pm

I recall someone alluding to an alternative route to nitroethane a while back on the Hive. Can't find the post, though I have searched.