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Putrescine
Putrescine
Putrescine 3D
IUPAC name
Other names 1,4-diaminobutane
Identifiers
CAS number 110-60-1 Yes check.svgY
PubChem 1045
MeSH Putrescine
SMILES
Properties
Molecular formula C4H12N2
Molar mass 88.1516
Melting point

27 °C

Boiling point

158–160 °C

 Yes check.svgY (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.

Contents

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

  1. ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. pp. 212. ISBN 1566702232.  
  2. ^ Kamhi, Ellen, Ph.D., RN, HNC (2007). Alternative Medicine Magazine's Definitive Guide to Weight Loss. Celestial Arts. pp. 14. ISBN 1587612593. "Ornithine is converted by bowel bacteria into a toxic substance called putrescine, which in turn degrades into polyamines, such as spermadine, spermine, and cadaverine (literally meaning "the essence of dead cadavers")."  
  3. ^ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th Ed. ed.). http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile. Retrieved 2007-09-10.  
  4. ^ "DSM Engineering Plastics". http://www.dsm.com/en_US/html/dep/stanyl.htm. Retrieved 2007-09-10.  
  5. ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats







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