Chemistry:Putrescine

From HandWiki
Short description: Foul-smelling organic chemical compound produced by the breakdown of amino acids
Putrescine
Skeletal formula of putrescine
Ball and stick model of putrescine
Names
Preferred IUPAC name
Butane-1,4-diamine
Other names
1,4-Diaminobutane, 1,4-Butanediamine
Identifiers
3D model (JSmol)
3DMet
605282
ChEBI
ChEMBL
ChemSpider
DrugBank
EC Number
  • 203-782-3
1715
KEGG
MeSH Putrescine
RTECS number
  • EJ6800000
UNII
UN number 2928
Properties
C4H12N2
Molar mass 88.154 g·mol−1
Appearance Colourless crystals
Odor fishy-ammoniacal, pungent
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
Vapor pressure 2.33 mm Hg at 25 deg C (est)
3.54x10−10 atm-cu m/mol at 25 deg C (est)
1.457
Hazards
GHS pictograms GHS02: Flammable GHS05: Corrosive GHS06: Toxic
GHS Signal word DANGER
H228, H302, H312, H314, H331
P210, P261, P280, P305+351+338, P310
Flash point 51 °C (124 °F; 324 K)
Explosive limits 0.98–9.08%
Lethal dose or concentration (LD, LC):
  • 463 mg kg−1 (oral, rat)
  • 1.576 g kg−1 (dermal, rabbit)
Related compounds
Related alkanamines
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references
Tracking categories (test):

Putrescine is an organic compound with the formula NH2(CH2)4NH2. A colorless liquid, it is related to cadaverine; both are produced by the breakdown of amino acids. 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.[1] They are also found in semen and some microalgae, together with related molecules like spermine and spermidine. The polyamines, of which putrescine is one of the simplest, appear to be factors necessary for proper eukaryotic cell division.

Production

Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[2][3][4]

Putrescine is produced on an industrial scale by hydrogenation of succinonitrile.[5] It reacts with adipic acid to yield the polyamide Nylon 46, which is marketed by DSM under the trade name Stanyl.[6]

Biotechnological production of putrescine from renewable feedstock has been investigated. A metabolically engineered strain of Escherichia coli that produces putrescine at high titer in glucose mineral salts medium has been described.[7]

Biochemistry

Biosynthesis of spermidine and spermine from putrescine. Ado = 5'-adenosyl.

Spermidine synthase uses putrescine and S-adenosylmethioninamine (decarboxylated S-adenosyl methionine) to produce spermidine. Spermidine in turn is combined with another S-adenosylmethioninamine 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.

Uses

Application of putrescine, along with other polyamines, can be used to extend the shelf life of fruits by delaying the ripening process.[9] Pre-harvest application of putrescine has been shown to increase plant resistance to high temperatures and drought.[10] Both of these effects seem to result from lowered ethylene production following exogenous putrescine exposure.[11]

Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing.[12]

Toxicity

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).[13]

In humans, molecular modelling and docking experiments have shown that putrescine fits into the binding pocket of the human TAAR6 and TAAR8 receptors.[14]

Further reading

See also

References

  1. 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. Bibcode2013PLoSO...856111Y. 
  2. Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
  3. 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.)
  4. Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.
  5. "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a17_363/current/html?hd=All%2Csuccinonitrile. Retrieved 2007-09-10. 
  6. "Electronic Control Modules (ECU) - Electrical & Electronics - Applications - DSM". http://www.dsm.com/markets/automotive/en_US/applications/automotive-ee/electronic-control-modules.html. 
  7. Qian, Zhi-Gang; Xia, Xiao-Xia; Yup Lee, Sang (2009). "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Biotechnology and Bioengineering 104 (4): 651–662. doi:10.1002/bit.22502. PMID 19714672. 
  8. Srivenugopal KS, Adiga PR (September 1981). "Enzymic conversion of agmatine to putrescine in Lathyrus sativus seedlings. Purification and properties of a multifunctional enzyme (putrescine synthase).". J. Biol. Chem. 256 (18): 9532–41. doi:10.1016/S0021-9258(19)68795-8. PMID 6895223. 
  9. Abbasi, Nadeem Akhtar; Ali, Irfan; Hafiz, Ishfaq Ahmad; Alenazi, Mekhled M.; Shafiq, Muhammad (January 2019). "Effects of Putrescine Application on Peach Fruit during Storage" (in en). Sustainability 11 (7): 2013. doi:10.3390/su11072013. https://www.mdpi.com/2071-1050/11/7/2013. 
  10. Todorov, D.; Alexieva, V.; Karanov, E. (1998-12-01). "Effect of Putrescine, 4-PU-30, and Abscisic Acid on Maize Plants Grown under Normal, Drought, and Rewatering Conditions" (in en). Journal of Plant Growth Regulation 17 (4): 197–203. doi:10.1007/PL00007035. ISSN 1435-8107. https://doi.org/10.1007/PL00007035. 
  11. Khan, A.S.; Z. Singh (May 2008). "INFLUENCE OF PRE AND POSTHARVEST APPLICATIONS OF PUTRESCINE ON ETHYLENE PRODUCTION, STORAGE LIFE AND QUALITY OF 'ANGELINO' PLUM". Acta Horticulturae (768): 125–133. doi:10.17660/ActaHortic.2008.768.14. ISSN 0567-7572. https://www.actahort.org/books/768/768_14.htm. 
  12. Pelletti, Guido; Garagnani, Marco; Barone, Rossella; Boscolo-Berto, Rafael; Rossi, Francesca; Morotti, Annalisa; Roffi, Raffaella; Fais, Paolo et al. (2019-04-01). "Validation and preliminary application of a GC–MS method for the determination of putrescine and cadaverine in the human brain: a promising technique for PMI estimation" (in en). Forensic Science International 297: 221–227. doi:10.1016/j.forsciint.2019.01.025. ISSN 0379-0738. https://www.sciencedirect.com/science/article/pii/S0379073819300283. 
  13. Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology 35 (3–4): 337–348. doi:10.1016/S0278-6915(97)00121-X. ISSN 0278-6915. PMID 9207896. 
  14. Izquierdo, C; Gomez-Tamayo, JC; Nebel, J-C; Pardo, L; Gonzalez, A (2018). "Identifying human diamine sensors for death related putrescine and cadaverine molecules.". PLOS Computational Biology 14 (1): e1005945. doi:10.1371/journal.pcbi.1005945. PMID 29324768. Bibcode2018PLSCB..14E5945I. 

External links