Sciencemadness Discussion Board

Obtaining Cadaverine and/or Putrescine from rotting material

l.student - 5-4-2012 at 00:02

Has anyone attempted this? If so, how did you proceed? How would you go about it?
Would washing/bathing source material (rotting flesh) in solvent (what would be a good solvent) and then distilling it work?

EDIT

The purpose of this exercise is to extract foul smelling chemicals (from something dead) in order to release them in a controlled fashion at a time and date of my choosing. My summary research led me to believe that Putrescine ( NH2(CH2)4NH2 , 1,4-diaminobutane or butanediamine ) and Cadaverine ( NH2(CH2)5NH2 , 1,5-pentanediamine or pentamethylenediamine ) are the primary factors in why dead things smell the way they do.

I'm basically thinking of using ethanol to try and lift the compounds that interest me from my "source material" and then evaporate the ethanol away. However I'm pretty darn sure that I won't only pick up NH2(CH2)5NH2 (Cadaverine) and NH2(CH2)4NH2 (Putrescine) but a whole lot of other things that will interact with each other and possibly the solvent to a result that, given my level of experience or knowledge of chemistry, I cannot determine. Presuming that up 'till here everything goes well I'll probably end up with a rather nasty mix of lots of different compounds, which should, in my opinion, also contain the two I mentioned above.

Now, given that the purpose of this exercise, is the process outlined above appropriate? Will I obtain a mixture that will smell of rotting meat? Would you use a solvent other than ethanol? If so, which one and why? How would you do this differently and why?

Sorry for the pre-edit version of the post. It was... Crap. (Not to say that this one is better)

[Edited on 5-4-2012 by l.student]

[Edited on 5-4-2012 by l.student]

[Edited on 5-4-2012 by l.student]

[Edited on 5-4-2012 by l.student]

arsphenamine - 5-4-2012 at 06:52

Quote: Originally posted by l.student  


The purpose of this exercise is to extract foul smelling chemicals (from something dead) in order to release them in a controlled fashion at a time and date of my choosing. My summary research led me to believe that Putrescine ( NH2(CH2)4NH2 , 1,4-diaminobutane or butanediamine ) and Cadaverine ( NH2(CH2)5NH2 , 1,5-pentanediamine or pentamethylenediamine ) are the primary factors in why dead things smell the way they do.

I'm basically thinking of using ethanol to try and lift the compounds that interest me from my "source material" and then evaporate the ethanol away. However I'm pretty darn sure that I won't only pick up NH2(CH2)5NH2 (Cadaverine) and NH2(CH2)4NH2 (Putrescine) but a whole lot of other things that will interact with each other and possibly the solvent to a result that, given my level of experience or knowledge of chemistry, I cannot determine.


There is an extraction procedure in the article Polyamines in Soybean

It exploits the property of small alkyl polyamines being basic. Putrescine's pKa's are at 11.2 and 9.7.

l.student - 5-4-2012 at 10:10

Thank you very much. I'd much rather use soybeans anyway.

arsphenamine - 5-4-2012 at 11:05

You are very welcome.

Don't stop with that article. There are other methods out there.

A search on "putrescine extraction" gives a lot of useful hits, even abstracts.
<a href="http://www.ncbi.nlm.nih.gov/pubmed/21919350"><b>This abstract</b></a> mentions using 75% aqeuous methanol acidified with HCl to extract putrescine from fish.

Once you have the extract, reduce the solvent volume gently,
make it alkaline with OH<sup>-</sup> or carbonate to
generate the free amine, and extract with ether or chloroform.

pedrovecchio - 11-4-2012 at 21:48

Here is the paper arsphenamine reffered to.

Attachment: richard2011.pdf (381kB)
This file has been downloaded 1239 times

l.student - 11-4-2012 at 22:02

Thanks pedrovecchio! I really didn't know where to download the full text from. Really not used to that sort of site. I also think I needed to register or something...