Putrescine

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Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Identifiers
CAS number110-60-1 YesY
PubChem1045
ChemSpider13837702 YesY
EC number203-782-3
UN number2928
DrugBankDB01917
KEGGC02896 YesY
MeSHPutrescine
ChEBICHEBI:17148 N
ChEMBLCHEMBL46257 YesY
IUPHAR ligand2388
RTECS numberEJ6800000
Beilstein Reference605282
Gmelin Reference1715
3DMetB00037
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H12N2
Molar mass88.15 g mol−1
AppearanceColourless crystals
Odorstrong, piperidine-like
Density0.877 g/mL
Melting point27.5 °C (81.5 °F; 300.6 K)
Boiling point158.6 °C; 317.4 °F; 431.7 K
Solubility in waterMiscible
log P−0.466
Refractive index (nD)1.457
Hazards
GHS pictogramsThe 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 wordDANGER
GHS hazard statementsH228, H302, H312, H314, H331
GHS precautionary statementsP210, P261, P280, P305+351+338, P310
EU classificationHighly Flammable F Toxic T
R-phrasesR11, R21/22 R23, R34
S-phrasesS16, S26, S36/37/39, S45
Flash point51 °C (124 °F; 324 K)
Explosive limits0.98–9.08%
LD50
  • 463 mg kg−1 (oral, rat)
  • 1.576 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Related compounds2-Methyl-2-nitrosopropane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references
 
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Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Identifiers
CAS number110-60-1 YesY
PubChem1045
ChemSpider13837702 YesY
EC number203-782-3
UN number2928
DrugBankDB01917
KEGGC02896 YesY
MeSHPutrescine
ChEBICHEBI:17148 N
ChEMBLCHEMBL46257 YesY
IUPHAR ligand2388
RTECS numberEJ6800000
Beilstein Reference605282
Gmelin Reference1715
3DMetB00037
Jmol-3D imagesImage 1
Properties
Molecular formulaC4H12N2
Molar mass88.15 g mol−1
AppearanceColourless crystals
Odorstrong, piperidine-like
Density0.877 g/mL
Melting point27.5 °C (81.5 °F; 300.6 K)
Boiling point158.6 °C; 317.4 °F; 431.7 K
Solubility in waterMiscible
log P−0.466
Refractive index (nD)1.457
Hazards
GHS pictogramsThe 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 wordDANGER
GHS hazard statementsH228, H302, H312, H314, H331
GHS precautionary statementsP210, P261, P280, P305+351+338, P310
EU classificationHighly Flammable F Toxic T
R-phrasesR11, R21/22 R23, R34
S-phrasesS16, S26, S36/37/39, S45
Flash point51 °C (124 °F; 324 K)
Explosive limits0.98–9.08%
LD50
  • 463 mg kg−1 (oral, rat)
  • 1.576 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Related compounds2-Methyl-2-nitrosopropane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Putrescine, or tetramethylenediamine, is a foul-smelling[2] organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine) that 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.[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[edit]

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

Production[edit]

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[edit]

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[edit]

Putrescine is toxic in large doses. In rats it had a fairly low acute oral toxicity of 2000 mg/kg body weight.[12]

See also[edit]

References[edit]

  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. ISBN 0-8493-9434-1. 
  3. ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212. ISBN 1-56670-223-2. 
  4. ^ Kamhi, Ellen, Ph.D., RN, HNC (2007). Alternative Medicine Magazine's Definitive Guide to Weight Loss. Celestial Arts. p. 14. ISBN 1-58761-259-3. "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")." 
  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. doi:10.1371/journal.pone.0056111. PMID 23405259. 
  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[edit]