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| | Spermidine Basic information |
| Product Name: | Spermidine | | Synonyms: | 1,8-DIAMINO-4-AZAOCTANE;SPERMIDINE FREE BASE;SPERMIDINE;OMEGA-AMINOBUTYL-OMEGA-AMINOPROPYLAMINE;N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE;N-(3-AMINOPROPYL)-1,4-BUTANDIAMINE;N-[3-AMINOPROPYL]-1,4-BUTANEDIAMINE;N-(3-AMINOPROPYL)-1,4-DIAMINOBUTANE | | CAS: | 124-20-9 | | MF: | C7H19N3 | | MW: | 145.25 | | EINECS: | 204-689-0 | | Product Categories: | co-factor;124-20-9 | | Mol File: | 124-20-9.mol |  |
| | Spermidine Chemical Properties |
| Melting point | 23-25 °C | | Boiling point | 128-130 °C (14 mmHg) | | density | 1.00 g/mL at 20 °C | | refractive index | n20/D 1.479(lit.) | | Fp | >230 °F | | storage temp. | room temp | | solubility | H2O: 1 M at 20 °C, clear, colorless | | form | Liquid After Melting | | pka | 10.53±0.19(Predicted) | | color | Clear colorless | | Specific Gravity | 0.925 | | Odor | Ichtyal, ammoniacal | | PH | 12.0-13.5 (25℃, 1M in H2O) | | Water Solubility | Miscible with water, ethanol and ether. | | λmax | λ: 260 nm Amax: 0.1
λ: 280 nm Amax: 0.05 | | Sensitive | Air Sensitive | | Merck | 14,8742 | | BRN | 1698591 | | Stability: | Stable, but air-sensitive and very hygroscopic - store under argon. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents. | | InChIKey | ATHGHQPFGPMSJY-UHFFFAOYSA-N | | CAS DataBase Reference | 124-20-9(CAS DataBase Reference) | | EPA Substance Registry System | 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9) |
| Hazard Codes | C | | Risk Statements | 34 | | Safety Statements | 26-36/37/39-45-27 | | RIDADR | UN 2735 8/PG 2 | | WGK Germany | 3 | | RTECS | EJ7000000 | | F | 3-10-34 | | TSCA | Yes | | HazardClass | 8 | | PackingGroup | III | | HS Code | 29212900 |
| | Spermidine Usage And Synthesis |
| Description | Spermidine is an endogenous polyamine. It is formed from putrescine by spermidine synthase. | | Chemical Properties | Spermidine solution is a colorless clear liquid with very hygroscopic and oxidizable. It is soluble in water (50 mg/ml), ethanol, and ether. | | Source | Spermidine is found in fresh green pepper, wheat germ, cauliflower, broccoli, mushrooms, and a variety of cheeses. Even higher amounts are found in soybean products such as natto, shitake mushrooms, amaranth grain and durian. Some of these ingredients are particularly common in a Mediterranean diet, which may explain why some believe eating like the Spanish can prolong your life. | | Uses | Spermidine can be used in electroporation while transferring the DNA into the cell under the electrical impulse. May be used for purification of DNA-binding proteins. Spermidine is also used, along with calcium chloride, for precipitating DNA onto microprojectiles for bombardment with a gene gun. | | Application | Spermidine serves as a precursor of spermine and essential for both normal and neoplastic tissue growth. It was first detected in human sperm, but occurs widely in nature. It is essential in both normal and neoplastic tissue growth. Spermidine has a role in cell growth processes and the formation and interconversion of spermidine in mammalian cells has been reported. It has been studied in the regulation of tRNA methyltransferase activity and stimulates T4 polynucleotide kinase activity. | | Definition | ChEBI: Spermidine is a triamine that is the 1,5,10-triaza derivative of decane. It is a polyamine that is routinely included in restriction enzyme digestions to improve the cleavage efficacy of the DNA. Spermidine counteracts the inhibitory effects of contaminants coisolated with DNA and consequently permits complete digestion of the DNA at lower enzyme concentrations. | | Preparation | The linker resin 2 was used in the synthesis of spermidine. In order to initiate the preparation the 2-nitrossulfonamide was anchored on the resin 2 by reaction in THF under reflux. The resulting resin 3 then reacted with 4-bromobutylphthalimide in acetonitrile in the presence of Cs2CO3 as base, generating the resin 4. Protected spermidine 5 was cleaved from resin 4 after treatment with hydrate hydrazine at room temperature. Spermidine 5 was previously prepared by our group in solution system utilizing Fukuyama's sulfonamide.
Synthesis and Characterization of a Linker for Primary Amines used in the Solid Phase Organic Synthesis of Spermidine
J. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011
DOI: 10.1590/S0103-50532011000100011 | | benefits | The biggest benefit of spermidine is its ability to reduce age-related diseases. It benefits cardioactive, spermidine can reduce the development of atherosclerosis in mice by reducing inflammation and improving cellular (mitochondria) function. It can reduce the formation of blood clots (platelet aggregation) and improve the normal dilation of cells lining blood vessels. Spermidine lowers blood pressure, improves energy use, and reduces heart cell death. It prevents neurologic diseases, and spermidine helps reduce cognitive, memory, and functional impairment associated with aging. It can also Decrease blood sugar levels, Increase autophagy, Increase bone strength, and have Anti-inflammatory effects. | | Mode of action | Spermidine's main mechanism of action is its ability to induce autophagy, a self-preservation process which clears out toxic, damaged and dysfunctional cells, resulting in lower levels of inflammation in the body. Autophagy is the main mechanism of spermidine in delaying aging and prolonging the lifespan. In addition, spermidine exerts its effects through other mechanisms, including anti-inflammation, histone acetylation reduction, lipid metabolism and regulation of cell growth and signaling pathways. | | References | Madeo, F., Eisenberg, T., Pietrocola, F., et al. Spermidine in health and disease. Science 359(6374), eaan2788 (2018).
Lopatin, A.N., Makhina, E.N., and Nichols, C.G. Potassium channel block by cytoplasmic polyamines as the mechanism of intrinsic rectification. Nature 372(6504), 366-369 (1994).
Eisenberg, T., Knauer, H., Schauer, A., et al. Induction of autophagy by spermidine promotes longevity. Nat. Cell Biol. 11(11), 1305-1314 (2009).
Guo, X., Harada, C., Namekata, K., et al. Spermidine alleviates severity of murine experimental autoimmune encephalomyelitis. Invest. Ophthalmol. Vis. Sci. 52(5), 2696-2703 (2011).
Eisenberg, T., Abdellatif, M., Schroeder, S., et al. Cardioprotection and lifespan extension by the natural polyamine spermidine. Nat. Med. 22(12), 1428-1438 (2016). |
| | Spermidine Preparation Products And Raw materials |
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