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Spermidine

CAS No.
124-20-9
Chemical Name:
Spermidine
Synonyms
SperMidin;N1-(3-AMINOPROPYL)BUTANE-1,4-DIAMINE;Spermidine-Rich Wheat Germ Extract;1,4-Butanediamine, N-(3-aminopropyl)-;3.2 Kg;Spermidie;Spemidine;SPERMIDINE;SPERMIDINE(RG);Spermidine,99%
CBNumber:
CB2165662
Molecular Formula:
C7H19N3
Molecular Weight:
145.25
MDL Number:
MFCD00008229
MOL File:
124-20-9.mol
MSDS File:
SDS
Last updated:2024-04-19 14:39:40

Spermidine 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.)
Flash point >230 °F
storage temp. room temp
solubility H2O: 1 M at 20 °C, clear, colorless
pka 10.53±0.19(Predicted)
form Liquid After Melting
color Clear colorless
Specific Gravity 0.925
PH 12.0-13.5 (25℃, 1M in H2O)
Odor Ichtyal, ammoniacal
Water Solubility Miscible with water, ethanol and ether.
Sensitive Air Sensitive
λmax λ: 260 nm Amax: 0.1
λ: 280 nm Amax: 0.05
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)
EWG's Food Scores 1
FDA UNII U87FK77H25
EPA Substance Registry System 1,4-Butanediamine, N-(3-aminopropyl)- (124-20-9)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS05
Signal word  Danger
Hazard statements  H314
Precautionary statements  P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
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
3-10-34
TSCA  Yes
HazardClass  8
PackingGroup  III
HS Code  29212900
NFPA 704
1
3 1

Spermidine price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 49761 Spermidine analytical standard 124-20-9 100mg $75.1 2024-03-01 Buy
Sigma-Aldrich 05292 Spermidine 0.1 M solution 124-20-9 1ML-F $73.4 2024-03-01 Buy
Sigma-Aldrich 05292 Spermidine 0.1 M solution 124-20-9 1mL $70 2023-01-07 Buy
Alfa Aesar A19096 Spermidine, 99% 124-20-9 1g $43.9 2024-03-01 Buy
Alfa Aesar A19096 Spermidine, 99% 124-20-9 5g $127 2024-03-01 Buy
Product number Packaging Price Buy
49761 100mg $75.1 Buy
05292 1ML-F $73.4 Buy
05292 1mL $70 Buy
A19096 1g $43.9 Buy
A19096 5g $127 Buy

Spermidine Chemical Properties,Uses,Production

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 of spermidine
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

Origin

Spermidine was first discovered in 1678 by Dutch scientist Anton Van Leeuwenhoek in a sample of human semen. Shortly after, spermidine was discovered in human sperm. In the body, spermidine is created from its precursor putrescine.

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.

Side effects

The side effects of Spermidine included decreased levels of creatinine, calcium, and phosphate in the blood. These are markers of kidney function and electrolyte balance in the body, and if they are altered, it could signify a health problem. In particular, Spermidine supplements have not been tested in pregnant or nursing women. Another large observational study was done in humans that showed a link between higher blood levels of spermidine and an increased risk of stroke. Many supplemental forms of spermidine are derived from wheat germ. As a result, there may be trace levels of gluten in these supplements. For people with celiac disease, wheat allergy, or gluten sensitivity, it's important to check labels and choose a gluten-free supplement.

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).

103493-34-1
124-20-9
Synthesis of Spermidine from Carbamic acid, N-[4-[(3-aminopropyl)amino]butyl]-, 1,1-dimethylethyl ester
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View Lastest Price from Spermidine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
spermidine pictures 2024-04-24 spermidine
124-20-9
US $9.00-70.00 / g 10g 99% 10 tons Hebei Kangcang new material Technology Co., LTD
Spermidine pictures 2024-04-24 Spermidine
124-20-9
US $1.00 / g 1g 99% 100kg Wuhan Cell Pharmaceutical Co., Ltd
Spermidine pictures 2024-04-24 Spermidine
124-20-9
US $8.00-1.00 / kg 1kg 99% 300tons Hebei Dangtong Import and export Co LTD
  • spermidine pictures
  • spermidine
    124-20-9
  • US $9.00-70.00 / g
  • 99%
  • Hebei Kangcang new material Technology Co., LTD
  • Spermidine pictures
  • Spermidine
    124-20-9
  • US $1.00 / g
  • 99%
  • Wuhan Cell Pharmaceutical Co., Ltd
  • Spermidine pictures
  • Spermidine
    124-20-9
  • US $8.00-1.00 / kg
  • 99%
  • Hebei Dangtong Import and export Co LTD
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