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Putrescine

 

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Putrescine


 
 

Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NNitrogen

Nitrogen is a chemical element which has the symbol N and atomic number 7 in the periodic table....
HHydrogen

|-| Triple point || 13.8033 K, 7.042 kPa...
2(CCarbon

Carbon is a chemical element in the periodic table that has the symbol C and atomic number 6....
H2)4NH2 (1,4-diaminobutane or butanediamine). It is related to cadaverineCadaverine

Cadaverine is a foul-smelling molecule produced by protein hydrolysis during putrefaction of animal tissue....
; both are produced by the breakdown of amino acidAmino acid

In chemistry, an amino acid is any molecule that contains both amine and carboxyl functional groups....
s in living and dead organisms and both are toxic in large doses. The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semenSemen

Semen is an organic fluid that usually contains spermatozoa....
 and some microalgae, together with related molecules like spermineSpermine

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells....
 and spermidineSpermidine

Spermidine is a polyamine involved in cellular metabolism that can be used to stimulate the enzyme, T7 rna polymerase, a typ...
.

History

Putrescine and cadaverine were first described by the BerlinBerlin

Berlin is the capital city and a state of Germany....
 physician Ludwig Brieger in 1885.

Production and use

Putrescine is produced on industrial scale by hydrogenationHydrogenation

Hydrogenation is a class of chemical reactions in which the net result is an addition of hydrogen....
 of succinonitrileSuccinonitrile

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H42....
, which is produced by addition of hydrogen cyanideFacts About Hydrogen cyanide

Hydrogen cyanide is a chemical compound with chemical formula HCN....
 to acrylonitrileAcrylonitrile

Acrylonitrile is the chemical compound with the formula CH2CHCN....
. Putrescine is reacted with adipic acidAdipic acid

Adipic acid is a chemical compound of the class of carboxylic acids....
 to yield the polyamidePolyamide

A polyamide is a polymer containing monomers joined by peptide bonds....
 NylonNylon

Nylon represents a family of synthetic polymers, a thermoplastic material, first produced on 28 February, 1935 by Gerard J....
-4,6, which is marketed by DSMDSM (company)

DSM is a multinational chemicals company....
 under the trade name Stanyl.

Biochemistry

Putrescine attacks s-adenosyl methionineS-Adenosyl methionine

S-adenosyl methionine is a biological compound involved in methyl group transfers, and is present in all living cells....
 and converts it to spermidineSpermidine

Spermidine is a polyamine involved in cellular metabolism that can be used to stimulate the enzyme, T7 rna polymerase, a typ...
. Spermidine in turn attacks another s-adenosyl methionineFacts About S-Adenosyl methionine

S-adenosyl methionine is a biological compound involved in methyl group transfers, and is present in all living cells....
 and converts it to spermineSpermine

Spermine is a polyamine involved in cellular metabolism found in all eukaryotic cells....
.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylaseOrnithine decarboxylase

The enzyme ornithine decarboxylase is a homodimer of 461 amino acids that catalyzes the decarboxylation of ornithine produci...
. The polyamineFacts About Polyamine

The polyamines are organic compounds having two or more primary amino groups - such as putrescine, cadaverine, spermidine, a...
s, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.

Toxicity

Putrescine is toxic in large doses. In rats it had a fairly low acute oral toxicity of 2000 mg/kg body weight.

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