 | |
 | |
| Names | |
|---|---|
| Preferred IUPAC name Butane-1,4-diamine | |
| Other names 1,4-Diaminobutane, 1,4-Butanediamine | |
| Identifiers | |
| |
3D model (JSmol) | |
| 605282 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
|
| DrugBank |
|
| ECHA InfoCard | 100.003.440 |
| EC Number |
|
| 1715 | |
| KEGG |
|
| MeSH | Putrescine |
| RTECS number |
|
| UNII | |
| UN number | 2928 |
| |
| |
| Properties | |
| C4H12N2 | |
| Molar mass | 88.154 g·mol−1 |
| Appearance | Colourless crystals |
| Odor | very unpleasant; putrid, fishy-ammoniacal |
| 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 | |
| logP | −0.466 |
| Vapor pressure | 2.33 mm Hg at 25 ºC (est) |
Henry's law constant (kH) | 3.54×10−10 atm·m3/mol at 25 ºC (est) |
Refractive index (nD) | 1.457 |
| Hazards | |
| GHS labelling: | |
   | |
| Danger | |
| H228,H302,H312,H314,H331 | |
| P210,P261,P280,P305+P351+P338,P310 | |
| Flash point | 51 °C (124 °F; 324 K) |
| Explosive limits | 0.98–9.08% |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
| Related compounds | |
Related alkanamines | |
Related compounds | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Putrescine is anorganic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as adiamine.[3] Together withcadaverine, it is largely responsible for the foul odor ofputrefying flesh, but also contributes to other unpleasant odors.
Putrescine is produced on an industrial scale by thehydrogenation ofsuccinonitrile.[3]
Biotechnological production of putrescine from a renewable feedstock has been investigated. A metabolically engineered strain ofEscherichia coli that produces putrescine at high concentrations in glucose mineral salts medium has been described.[4]
Spermidine synthase uses putrescine andS-adenosylmethioninamine (decarboxylatedS-adenosyl methionine) to producespermidine. Spermidine in turn is combined with anotherS-adenosylmethioninamine and gets converted tospermine.
Putrescine is synthesized in small quantities by healthy living cells by the action ofornithine decarboxylase.
Putrescine is synthesized biologically via two different pathways, both starting fromarginine.
Putrescine, viametabolic intermediates includingN-acetylputrescine,γ-aminobutyraldehyde (GABAL),N-acetyl-γ-aminobutyric acid (N-acetyl-GABAL), andN-acetyl-γ-aminobutyric acid (N-acetyl-GABA),biotransformations mediated bydiamine oxidase (DAO),monoamine oxidase B (MAO-B),aminobutyraldehyde dehydrogenase (ABALDH), and otherenzymes, can act as a minorbiological precursor ofγ-aminobutyric acid (GABA) in thebrain and elsewhere.[6][7][8][9][10][11] In 2021, it was discovered that MAO-B does not mediatedopaminecatabolism in the rodentstriatum but instead participates in striatal GABA synthesis and that synthesized GABA in turn inhibitsdopaminergicneurons in this brain area.[12][11] It has been found that MAO-B, via the putrescine pathway, importantly mediates GABA synthesis inastrocytes in various brain areas, including in thehippocampus,cerebellum, striatum,cerebral cortex, andsubstantia nigra pars compacta (SNpc).[12][11]
Putrescine is found in allorganisms.[13] Putrescine is widely found in plant tissues,[13] often being the most common polyamine present within the organism. Its role in development is well documented, but recent studies have suggested that putrescine also plays a role in stress responses in plants, both to biotic and abiotic stressors.[14] The absence of putrescine in plants is associated with an increase in both parasite and fungal population in plants.
Putrescine serves an important role in a multitude of ways, which include: acation substitute, anosmolyte, or a transport protein.[13] It also serves as an important regulator in a variety of surface proteins, both on the cell surface and on organelles, such as the mitochondria and chloroplasts. A recorded increase of ATP production has been found in mitochondria and ATP synthesis by chloroplasts with an increase in mitochondrial and chloroplastic putrescine, but putrescine has also been shown to function as a developmental inhibitor in some plants, which can be seen asdwarfism and late flowering inArabidopsis plants.[13]
Putrescine production in plants can also be promoted by fungi in the soil.[15]Piriformospora indica (P. indica) is one such fungus, found to promote putrescine production inArabidopsis and common garden tomato plants. In a 2022 study it was shown that the presence of this fungus had a promotional effect on the growth of the root structure of plants. Aftergas chromatography testing, putrescine was found in higher amounts in these root structures.[16]
Plants that had been inoculated withP. indica had presented an excess of arginine decarboxylase.[16] This is used in the process of making putrescine in plant cells. One of the downstream effects of putrescine in root cells is the production ofauxin. That same study found that putrescine added as a fertilizer showed the same results as if it was inoculated with the fungus, which was also shown inArabidopsis andbarley. The evolutionary foundations of this connection and putrescine are still unclear.
Putrescine is a component ofbad breath andbacterial vaginosis.[17] It is also found insemen and some microalgae, together withspermine andspermidine.
Putrescine reacts withadipic acid to yield thepolyamidenylon 46, which is marketed by Envalior (formerlyDSM) under the trade name Stanyl.[18][19]
Application of putrescine, along with other polyamines, can be used to extend the shelf life of fruits by delaying the ripening process.[20] Pre-harvest application of putrescine has been shown to increase plant resistance to high temperatures and drought.[21] Both of these effects seem to result from lowered ethylene production following exogenous putrescine exposure.[22]
Due to its role in putrification, putrescine has also been proposed as a biochemical marker for determining how long a corpse has been decomposing.[23]
Putrescine together withchitosan has been successfully used inpostharvest physiology as a natural fruit coating.[24] Putrescine with chitosan treated fruits had higher antioxidant capacity andenzyme activities than untreated fruits. Freshstrawberries coated have lowerdecay percentage, higher tissue firmness, contents oftotal soluble solids. Nanoparticles of putrescine with chitosan are effective in preserving the nutritional quality and prolonging the post-harvest life of strawberries during storage up to 12 days.[24]
Putrescine andcadaverine were first described in 1885 by theBerlin physician Ludwig Brieger (1849–1919).[25][26][27]
In rats, putrescine has a lowacute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).[28]
Alternate pathways of GABA synthesis from putrescine and other polyamines have also been reported [207–211]. Here, γ-aminobutyraldehyde, an intermediate from polyamine degradation reaction via combined activities of diamine oxidase (DAO, E.C. 1.4.3.6) and 4-aminobutyraldehyde dehydrogenase (ABALDH), leads to the synthesis of GABA [205,212,213]. In response to abiotic stresses, GABA is also reported to be synthesized from proline via D1-pyrroline intermediate formation [47,205,214] and also by a nonenzymatic reaction [214]. However, GABA synthesis from polyamine pathways is minor in the brain, [215] although they play a significant role in the developing brain [216] and retina [217]. But GABA can be formed from putrescine in the mammalian brain [218].
MAO also catalyses the deamination of a natural brain constituent, monoacetyl-putrescine, producing y-acetylaminobutyraldehyde, which in turn participates in the formation of brain GABA [13].
