putrescine
American Heritage Dictionary:
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pu·tres·cine
(pyū-trĕs'ēn) 
n.
A colorless, foul-smelling ptomaine, NH2(CH2)4NH2, produced in decaying animal tissue by the decarboxylation of ornithine.
n.
A colorless, foul-smelling ptomaine, NH2(CH2)4NH2, produced in decaying animal tissue by the decarboxylation of ornithine.
[Latin putrēscere, to rot; see putrescent + -INE2.]
Oxford Dictionary of Biochemistry:
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putrescine
1,4-diaminobutane; the polyamine formed by decarboxylation of ornithine and the metabolic precursor of spermidine and spermine.
| putidaredoxin, purple membrane, purothionin | |
| pycnodysostosis, pycnometer, pyr-1 |
Saunders Veterinary Dictionary:
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putrescine
A polyamine first found in decaying meat; small quantities occur in most cells.
Mosby's Dental Dictionary:
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putrescine
n
A foul-smelling toxic ptomaine produced by the decomposition of the amino acid ornithine during the decay of animal tissues, bacillus cultures, and fecal bacteria.
Wikipedia on Answers.com:
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Putrescine
| Putrescine | |
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Butane-1,4-diamine[1] |
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Other names
1,4-Diaminobutane[citation needed] |
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| Identifiers | |
| CAS number | 110-60-1  |
| PubChem | 1045 |
| ChemSpider | 13837702 |
| EC number | 203-782-3 |
| UN number | 2928 |
| DrugBank | DB01917 |
| KEGG | C02896 |
| MeSH | Putrescine |
| ChEBI | CHEBI:17148  |
| ChEMBL | CHEMBL46257 |
| IUPHAR ligand | 2388 |
| RTECS number | EJ6800000 |
| Beilstein Reference | 605282 |
| Gmelin Reference | 1715 |
| 3DMet | B00037 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H12N2 |
| Molar mass | 88.15 g mol−1 |
| Appearance | Colourless crystals |
| Density | 877 mg mL−1 |
| Melting point |
27 °C, 300 K, 81 °F |
| Boiling point |
159 °C, 431.7 K, 317 °F |
| Solubility in water | Miscible |
| log P | −0.466 |
| Refractive index (nD) | 1.457 |
| Hazards | |
| GHS pictograms |    |
| GHS signal word | DANGER |
| GHS hazard statements | H228, H302, H312, H314, H331 |
| GHS precautionary statements | P210, P261, P280, P305+351+338, P310 |
| EU classification |  F  T |
| R-phrases | R11, R21/22 R23, R34 |
| S-phrases | S16, S26, S36/37/39, S45 |
| Flash point | 51 °C |
| Explosive limits | 0.98–9.08% |
| LD50 |
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| Related compounds | |
| Related alkanamines | |
| Related compounds | 2-Methyl-2-nitrosopropane |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Putrescine (sometimes spelled putrescin) 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. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.
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Contents
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History
Putrescine[5] and cadaverine[6] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[7]
Production
Putrescine is produced on industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile.[8] Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl.[9]
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 recently been described.[10]
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 2000 mg/kg body weight.[11]
References
- ^ "Putrescine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1045&loc=ec_rcs#x291. Retrieved 26 May 2012.
- ^ Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. pp. 100. ISBN 0-8493-9434-1.
- ^ Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. pp. 212. ISBN 1-56670-223-2.
- ^ Kamhi, Ellen, Ph.D., RN, HNC (2007). Alternative Medicine Magazine's Definitive Guide to Weight Loss. Celestial Arts. pp. 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")."
- ^ 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.)
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
- ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
- ^ "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th Ed. ed.). http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile. Retrieved 2007-09-10.
- ^ "DSM Engineering Plastics". http://www.dsm.com/en_US/html/dep/stanyl.htm. Retrieved 2007-09-10.
- ^ "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". http://www3.interscience.wiley.com/journal/122545238/abstract. Retrieved 2010-06-10.
- ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats
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Copyrights:
American Heritage Dictionary
The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.
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Oxford Dictionary of Biochemistry
Oxford University Press. Oxford Dictionary of Biochemistry and Molecular Biology © 1997, 2000, 2006 All rights reserved.
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Saunders Veterinary Dictionary
Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.
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Mosby's Dental Dictionary
Mosby's Dental Dictionary. Copyright © 2004 by Elsevier, Inc. All rights reserved.
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