putrescine

Putrescine
IUPAC name	butane-1,4-diamine
Other names	1,4-diaminobutane
Identifiers
CAS number	110-60-1 Y
PubChem	1045
MeSH	Putrescine
SMILES	NCCCCN
Properties
Molecular formula	C4H12N2
Molar mass	88.1516
Melting point	27 °C
Boiling point	158–160 °C
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Putrescine (sometimes spelled putrescin) is an organic chemical compound NH₂(CH₂)₄NH₂ (1,4-diaminobutane or butanediamine). It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms and both are toxic in large doses.^[1][2] 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 semen and some microalgae, together with related molecules like spermine and spermidine.

History

Putrescine and cadaverine were first described by the Berlin physician Ludwig Brieger in 1885.

Production and use

Putrescine is produced on industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile.^[3] Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.^[4]

Biochemistry

Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, 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^[5].

References