|Molar mass||88.15 g·mol−1|
|Melting point||27.5 °C (81.5 °F; 300.6 K)|
|Boiling point||158.6 °C; 317.4 °F; 431.7 K|
Refractive index (nD)
|GHS signal word||DANGER|
|H228, H302, H312, H314, H331|
|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 (124 °F; 324 K)|
LD50 (Lethal dose)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
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 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 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.
- "Putrescine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 26 May 2012.
- Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. p. 100. ISBN 0-8493-9434-1.
- Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212. ISBN 1-56670-223-2.
- 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").
- 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.
- 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.). Retrieved 2007-09-10.
- "DSM Engineering Plastics". Retrieved 2007-09-10.
- "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Retrieved 2010-06-10.
- Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats