Putrescine

Putrescine

Chembox new
ImageFile=Diaminobutane.pngImageSize=
ImageName=Putrescine
ImageFile1=Putrescine-stickAndBall.pngImageSize1=
ImageName1=Putrescine 3D
IUPACName=butane-1,4-diamine
OtherNames=
Section1= Chembox Identifiers
CASNo=110-60-1
PubChem=1045
SMILES=NCCCCN
MeSHName=Putrescine

Section2= Chembox Properties
Formula=C4H12N2
MolarMass=88.1516
Appearance=
Density=
MeltingPt={melting_point|27} °C
BoilingPt={boiling_point|158-160} °C
Solubility=

Section3= Chembox Hazards
MainHazards=
FlashPt=
Autoignition=

Putrescine (sometimes spelled putrescin or putrescene) 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. [cite book | last =Lewis | first =Robert Alan | title =Lewis' Dictionary of Toxicology | publisher =CRC Press | date =1998 | isbn =1566702232|pages=212 ] [cite book | last =Kamhi | first =Ellen, Ph.D., RN, HNC | title =Alternative Medicine Magazine's Definitive Guide to Weight Loss | publisher =Celestial Arts | date =2007 | pages =14 | isbn = 1587612593|quote=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").] 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 by the Berlinese 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. Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.

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 [http://cat.inist.fr/?aModele=afficheN&cpsidt=2714745] .

Cultural references

Putrescine is featured as a non-lethal weapon in the science fiction novel Zodiac, by Neal Stephenson. Its use is also suggested as a practical joke in [http://www.qwantz.com/archive/001155.html an episode] of Dinosaur Comics.

Notes

References

*cite encyclopedia
encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry
title = Nitriles
url = http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile
accessdate = 2007-09-10
edition = 7th Ed.

*cite web
url = http://www.dsm.com/en_US/html/dep/stanyl.htm
title = DSM Engineering Plastics
accessdate = 2007-09-10

External links

* [http://www.chm.bris.ac.uk/sillymolecules/sillymols.htm Molecules with silly names]


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Look at other dictionaries:

  • Putrescine — Formule semi développée de la putrescine. Général Nom IUPAC butane 1,4 diamine …   Wikipédia en Français

  • putrescine — [ pytresin ] n. f. • 1903; de putrescent ♦ Biochim. Polyamine d odeur nauséabonde, formée lors de la putréfaction des cadavres sous l action d enzymes bactériennes. ● putrescine nom féminin Substance qui se forme dans la putréfaction des cadavres …   Encyclopédie Universelle

  • putrescine — [pyo͞o tres′ēn, pyo͞o tres′in] n. 〚< L putrescere (see PUTRESCENT) + INE3〛 a foul smelling compound, NH2 (CH2) 4NH2, produced by bacterial fermentation of protein and in the normal metabolism of mammals: it is a precursor of spermine * * * …   Universalium

  • putrescine — [pyo͞o tres′ēn, pyo͞o tres′in] n. [< L putrescere (see PUTRESCENT) + INE3] a foul smelling compound, NH2 (CH2) 4NH2, produced by bacterial fermentation of protein and in the normal metabolism of mammals: it is a precursor of spermine …   English World dictionary

  • putrescine — putrescinas statusas T sritis chemija formulė H₂N(CH₂)₄NH₂ atitikmenys: angl. putrescine rus. путресцин ryšiai: sinonimas – tetrametilendiaminas …   Chemijos terminų aiškinamasis žodynas

  • Putrescine N-hydroxycinnamoyltransferase — In enzymology, a putrescine N hydroxycinnamoyltransferase (EC number|2.3.1.138) is an enzyme that catalyzes the chemical reaction:caffeoyl CoA + putrescine ightleftharpoons CoA + N caffeoylputrescineThus, the two substrates of this enzyme are… …   Wikipedia

  • Putrescine carbamoyltransferase — In enzymology, a putrescine carbamoyltransferase (EC number|2.1.3.6) is an enzyme that catalyzes the chemical reaction:carbamoyl phosphate + putrescine ightleftharpoons phosphate + N carbamoylputrescineThus, the two substrates of this enzyme are… …   Wikipedia

  • Putrescine N-methyltransferase — In enzymology, a putrescine N methyltransferase (EC number|2.1.1.53) is an enzyme that catalyzes the chemical reaction:S adenosyl L methionine + putrescine ightleftharpoons S adenosyl L homocysteine + N methylputrescineThus, the two substrates of …   Wikipedia

  • Putrescine oxidase — In enzymology, a putrescine oxidase (EC number|1.4.3.10) is an enzyme that catalyzes the chemical reaction:putrescine + O2 + H2O ightleftharpoons 4 aminobutanal + NH3 + H2O2The 3 substrates of this enzyme are putrescine, O2, and H2O, whereas its… …   Wikipedia

  • putrescine — noun Etymology: International Scientific Vocabulary, from Latin putrescere Date: 1887 a crystalline slightly poisonous ptomaine C4H12N2 that occurs in small amounts in virtually all living things …   New Collegiate Dictionary

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