WordNet

a colorless crystalline ptomaine with a foul odor that is produced in decaying animal matter

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/04/07 01:48:37」(JST)

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Putrescine, or tetramethylenediamine, is a foul-smelling^[1] 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.^[2]^[3] 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.^[4] They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.

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 an 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 46, 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 been described.^[10]

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.

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.^[11]
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).^[12]

References

^ 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. PMC 3566083. 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.). Retrieved 2007-09-10.
^ "Electronic Control Modules (ECU) - Electrical & Electronics - Applications - DSM". Dsm.com. Retrieved 18 December 2015.
^ "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Retrieved 2010-06-10.
^ 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. PMID 6895223.
^ 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.

External links

Putrescine MS Spectrum

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「プトレッシン」

Putrescine
Names
	Preferred IUPAC name Butane-1,4-diamine
	Other names 1,4-Diaminobutane
Identifiers
CAS Number	110-60-1 ;
3D model (Jmol)	Interactive image;
3DMet	B00037
Beilstein Reference	605282
ChEBI	CHEBI:17148 ;
ChemSpider	13837702 ;
DrugBank	DB01917 ;
ECHA InfoCard	100.003.440
EC Number	203-782-3
Gmelin Reference	1715
IUPHAR/BPS	2388;
KEGG	C02896 ;
MeSH	Putrescine
PubChem CID	1045;
RTECS number	EJ6800000
UN number	2928
	InChI InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2 Key: KIDHWZJUCRJVML-UHFFFAOYSA-N ;
	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
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 (DSD)	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)
Explosive limits	0.98–9.08%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	463 mg kg−1 (oral, rat); 1.576 g kg−1 (dermal, rabbit);
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).
	verify (what is ?)
	Infobox references

　　[★]

英: putrescine
同: テトラメチレンジアミン tetramethylendiamine
関: プトレシン、プトマイン

「プトレシン」

　　[★]

英: putrescine
関: プトレッシン

[1] Haglund, William (1996). Forensic taphonomy: The Postmortem Fate of Human Remains. CRC Press. p. 100. ISBN 0-8493-9434-1.

[2] Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212. ISBN 1-56670-223-2.

[3] 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").

[4] 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. PMC 3566083. PMID 23405259.

[5] 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.)

[6] Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39.

[7] Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.

[Ullmann-8] "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Retrieved 2007-09-10.

[9] "Electronic Control Modules (ECU) - Electrical & Electronics - Applications - DSM". Dsm.com. Retrieved 18 December 2015.

[Metabolic_Engineering_of_Escherichia_coli_for_the_Production_of_Putrescine:_A_Four_Carbon_Diamine-10] "Metabolic Engineering of Escherichia coli for the Production of Putrescine: A Four Carbon Diamine". Retrieved 2010-06-10.

[11] 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. PMID 6895223.

[12] 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.

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putrescine