Putrescine

Putrescine

Names
IUPAC name Butane-1,4-diamine
Other names 1,4-Diaminobutane
Identifiers
CAS Number	110-60-1 Y
3DMet	B00037
Beilstein Reference	605282
ChEBI	CHEBI:17148 N
ChEMBL	ChEMBL46257 Y
ChemSpider	13837702 Y
DrugBank	DB01917 N
EC Number	203-782-3
Gmelin Reference	1715
IUPHAR/BPS	2388
Jmol 3D model	Interactive image
KEGG	C02896 Y
MeSH	Putrescine
PubChem	1045
RTECS number	EJ6800000
UN number	2928
InChI InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2 Y Key: KIDHWZJUCRJVML-UHFFFAOYSA-N Y
SMILES NCCCCN
Properties
Chemical 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; 300.6 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
Vapor pressure	{{{value}}}
Related compounds
Related alkanamines	Propylamine Isopropylamine 1,2-Diaminopropane 1,3-Diaminopropane Isobutylamine tert-Butylamine n-Butylamine sec-Butylamine Pentylamine Cadaverine
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 verify (what is YN ?)
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.

History

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

Production

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.

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.

Putrescine is synthesized biologically via two different pathways, both starting from arginine.

• In one pathway, arginine is converted into agmatine, with a reaction catalyzed by the enzyme arginine decarboxylase (ADC); then agmatine is transformed into N-carbamoylputrescine by agmatine imino hydroxylase (AIH). Finally, N-carbamoylputrescine is converted into putrescine.
• In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC).

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 has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).

See also

• Skatole

External links

• Putrescine MS Spectrum