Nevermore
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Putrescine & Co.
I was thinking about attempting a synth of putrescine, cadaverine, and those nasty smelling stuff..
I know they could be made of hydrolisys of Nylon but i have really no clue how the reaction should be attempted...
Any suggestion?
even a true synth to butyric acid will be welcome! 
[Edited on 14/7/2004 by Nevermore]
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The_Davster
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putrescine: The synth of putresine hydrochloridehere.
I was unable to find anthing on cadaverine and butryic acid unfortunatly.
Why would you want to make such things anyway?
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Nevermore
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the synth over there is too hard, i don't have hydrazine handy neither most of the other chemical involved..
thanks anyway, butyric acid should be easier, but the synt using butter and NaOH + Hcl for neutralization doesn't look good to me...sounds a
little kewl..
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thunderfvck
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Nice.
I'm very interested in foul smelling chemicals as well. Boy, if you could see the look on my face when I smell the post-reaction fluid and nearly
vomit...It would be like christmas all over again.
I also have been wondering about butyric acid, but haven't really been focusing my attenition on it completely. I have butane, that is all. I was
thinking that it would be possible to oxidize the butane to n-butanol and then further oxidize that to butyric acid, but this has not worked very
well.
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Nevermore
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what was your most successful reaction? (of course H2S is not valid!! )
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The_Davster
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Quote
"Tetramethylenediamine, known as putrescine, and pentamethylenediamine, known as cadaverine, occur among the bacterial decompositon products of
protiens. They arise from the decarboxylation of ornithine and lysine respectively
H2N(CH2)3CHNH2COOH(ornithine)--(bacteria)-->H2N(CH2)4NH2(putrescine) +CO2
H2N(CH2)4CHNH2COOH(lysine)---(bacteria)-->H2N(CH2)5NH2(cadaverine) + CO2"
Unfortunatly the type of bacteria is not given but there should be a way to do the decarboxylation without bacteria.
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I am a fish
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| Quote: | Originally posted by Nevermore
I was thinking about attempting a synth of putrescine, cadaverine...
I know they could be made of hydrolisys of Nylon... |
You are unlikely to get either from hydrolysis of nylon. Most modern nylon is a copolymer between 1,6-diaminohexane and hexandioic acid.
1,6-diaminohexane smells unpleasant, but it is not in the same league as putricine and cadaverine.
1f `/0u (4|\\| |234d 7|-|15, `/0u |234||`/ |\\|33d 70 937 0u7 /\\/\\0|23.
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Nevermore
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what about butyric then?
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Geomancer
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Nylon 6,6 (specificly the acid component) is actually a good precursor. Rather than use the procedure in orgsyn, try using a Hoffman degradation. With
any luck, the only reagents you'll need are ammonia and hypochlorite. The orgsyn page gives references, which I can't get to at the moment.
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Tungsten
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what about this:
tetrahydrofurane + HBr => 1,4-bromobuthane + potassium phthalimde => putrescine
best regards,
Tungsten
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knowledgehungry
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Butyric is CH3CH2CH2C=O
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OH Right? Well if you have butanol then all you have to do is oxidize it. DiChromate should work.
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thunderfvck
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Yes. Butanol. But who has 1-butanol? Where can I find 1-butanol OTC?
I tried to obtain 1-butanol by oxidizing butane. I had like 30% H2O2 in a beaker and I gassed the butane through it. Nothing happened. Perhaps this
was a tad dangeresque? I then proceeded to heat the H2O2 up and then gassed it, but it wasn't very hot because I was rather frightened.
Perhaps GABA (the amino acid NH2-butyric acid) can somehow lose it's NH2 group...and then you'd have the wrench stench of butryic. Ah,
GHB...
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knowledgehungry
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If you have access to Grignard reagents I could give you a synthesis for 1-butanol... But I highly doubt you do, or that you have the equipment to
complete the synthesis correctly.
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JohnWW
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What about 1,4-n-butanediol? It is supposed to be a good drug, and in spite of its similarity to ethanol and other alcohols it has been banned in
several countries because of its psychedelic effects. It should be easy to make.
John W.
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Reverend Necroticus Rex
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1,4-butanediol is converted to gammahydroxybutyrate using an alkali or alkaline earth hydroxide, 1,4-butanediol is also ingested, but AFAIK is more
toxic and harder on the liver than GHB, as well as supposedly tasting foul
The sun is shining on a brand new day
Blackened corpses burn where they were slain
Self-flagellation prompts him to confess, Bless me father, for I made this mess.
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Geomancer
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Are you sure, Reverend? I don't see how a simple alkali will selectively oxidize one of the alcohols. Perhaps you thought he was referring to the
lactone, which people do indeed often hydrolyse prior to consumption? In any case, you're right that they all get converted to GHB in the body.
These compounds aren't quite as accessable as you might think syntheticly. A while back I looked around for routes to them. I never did find
a holy grail process, though. 1C+3C reactions are the most obvious. For example, Michael addition of some sort of protected methy-alchohol type thing
to acrolein. Where to get the halogenated 1C precursor, though? I don't recall any nice 2C+2C reactions. I'm a real fan of surprising 4C
methods, but any one from OTC materials would take some development (and hydrazine) to get it to work. See the thread "Cyclobutanone?". The
most likely plan (to the lactone) may be the industriomimetic route of producing furan, reducing to THF (actually, this can be extracted from
plumber's cement, if you're lazy), and oxidizing. If you want the diol, you can reduce the acid, but this may need hydride reagents.
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Reverend Necroticus Rex
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Ooops, brainfart, I did indeed mean the lactone. I guess I just wasn't with it, It's late and I'm cranky
The sun is shining on a brand new day
Blackened corpses burn where they were slain
Self-flagellation prompts him to confess, Bless me father, for I made this mess.
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Nevermore
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| Quote: | Originally posted by Geomancer
Nylon 6,6 (specificly the acid component) is actually a good precursor. Rather than use the procedure in orgsyn, try using a Hoffman degradation. With
any luck, the only reagents you'll need are ammonia and hypochlorite. The orgsyn page gives references, which I can't get to at the moment.
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that could be interesting..
however, is not easy to know if a nylon fiber is nylon 6.6 or something else, so it will be needed plenty of "test and see how goes"
about orgsyn, well, looks like the website is down for me too...
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guaguanco
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| Quote: | Originally posted by Tungsten
what about this:
tetrahydrofurane + HBr => 1,4-bromobuthane + potassium phthalimde => putrescine |
This would certainly be the most practical route. You could probably react the dihalide with ammonia gas in dry methanol or dry ethanol.
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