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Putrescine

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Putrescine

Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
EC number
UN number 2928
DrugBank
KEGG  YesY
MeSH
ChEBI  N
ChEMBL  YesY
IUPHAR ligand
RTECS number EJ6800000
Beilstein Reference 605282
Gmelin Reference 1715
3DMet
Jmol-3D images Image 1
Properties
Molecular formula C4H12N2
Molar mass 88.15 g mol−1
Appearance Colourless crystals
Odor strong, piperidine-like
Density 0.877 g/mL
Melting point 27.5 °C (81.5 °F; 300.7 K)
Boiling point 158.6 °C; 317.4 °F; 431.7 K
Solubility in water Miscible
log P −0.466
Refractive index (nD) 1.457
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H228, H302, H312, H314, H331
GHS precautionary statements P210, P261, P280, P305+351+338, P310
EU classification Highly Flammable F Toxic T
R-phrases R11, R21/22 R23, R34
S-phrases S16, S26, S36/37/39, S45
Flash point 51 °C (124 °F; 324 K)
Explosive limits 0.98–9.08%
LD50
  • 463 mg kg−1 (oral, rat)
  • 1.576 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Related compounds 2-Methyl-2-nitrosopropane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

Putrescine, or tetramethylenediamine, is a foul-smelling[2] organic chemical compound [3][4] 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.[5] They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.

History

Putrescine[6] and cadaverine[7] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[8]

Production

Putrescine is produced on an industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile.[9] Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.[10]

Biotechnological production of putrescine from renewable feedstock is a promising alternative to the chemical synthesis. A metabolically engineered strain of Escherichia coli that produces putrescine at high titer in glucose mineral salts medium has been described.[11]

Biochemistry

Putrescine attacks decarboxylated S-adenosyl methionine and gets converted to spermidine. Spermidine in turn attacks another decarboxylated S-adenosyl methionine and gets converted 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 83 mg/kg body weight.[12]

See also

References

  1. ^ "Putrescine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 26 May 2012. 
  2. ^ Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. p. 100.  
  3. ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212.  
  4. ^ Kamhi, Ellen,  
  5. ^ Yeoman, CJ; Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M; Gomez, A; Ho, M; Leigh, SR; Stumpf, R; Creedon, DJ; Smith, MA; Weisbaum, JS; Nelson, KE; Wilson, BA; White, BA (2013). "A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.". PloS one 8 (2): e56111.  
  6. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43. From page 43: Ich nenne dasselbe Putrescin, von putresco, faul werden, vermodern, verwesen. (I call this [compound] "putrescine", from [the Latin word] putresco, to become rotten, decay, rot.)
  7. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
  8. ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
  9. ^ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th Ed. ed.). Retrieved 2007-09-10. 
  10. ^ "DSM Engineering Plastics". Retrieved 2007-09-10. 
  11. ^ "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Retrieved 2010-06-10. 
  12. ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats

External links

  • Putrescine MS Spectrum
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