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Putrescine

Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Names
Preferred IUPAC name
Butane-1,4-diamine
Other names
1,4-Diaminobutane
Identifiers
110-60-1 YesY
3D model (Jmol) Interactive image
3DMet B00037
605282
ChEBI CHEBI:17148 N
ChEMBL ChEMBL46257 YesY
ChemSpider 13837702 YesY
DrugBank DB01917 N
ECHA InfoCard 100.003.440
EC Number 203-782-3
1715
2388
KEGG C02896 YesY
MeSH Putrescine
PubChem 1045
RTECS number EJ6800000
UN number 2928
Properties
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; 300.6 K)
Boiling point 158.6 °C; 317.4 °F; 431.7 K
Miscible
log P −0.466
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
H228, H302, H312, H314, H331
P210, P261, P280, P305+351+338, P310
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%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
  • 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 otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Putrescine, or tetramethylenediamine, is a foul-smelling 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. 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.

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

Putrescine is produced on an industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile. Putrescine is reacted with adipic acid to yield the polyamide Nylon 46, which is marketed by DSM under the trade name Stanyl. 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.

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.


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