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124-20-9

  • Product Name:Spermidine
  • Molecular Formula:C7H19N3
  • Molecular Weight:145.248
  • Appearance:Colorless clear liquid
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Product Details

pd_meltingpoint:23-25 °C

Appearance:Colorless clear liquid

Purity:99%

Top quality factory supply 124-20-9 Spermidine at low price

  • Molecular Formula:C7H19N3
  • Molecular Weight:145.248
  • Appearance/Colour:Colorless clear liquid 
  • Vapor Pressure:0.0269mmHg at 25°C 
  • Melting Point:23-25 °C 
  • Refractive Index:n20/D 1.479(lit.)  
  • Boiling Point:246.57 °C at 760 mmHg 
  • PKA:10.53±0.19(Predicted) 
  • Flash Point:118.078 °C 
  • PSA:64.07000 
  • Density:0.906 g/cm3 
  • LogP:1.45520 

Spermidine(Cas 124-20-9) Usage

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.

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 SpermidineJ. Braz. Chem. Soc., Vol. 22, No. 1, 86-91, 2011DOI: 10.1590/S0103-50532011000100011

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.

General Description

Spermidine is a naturally occurring polyamine involved in cellular growth regulation and protein synthesis, with potential implications in cancer therapy due to its role in modulating ornithine decarboxylase (ODC) activity and influencing neoplastic cell proliferation. Its analogs and derivatives have been explored for their antineoplastic properties, particularly in targeting malignancies such as melanoma and carcinoma. Additionally, spermidine's interaction with ODC highlights its significance in polyamine metabolism, making it a candidate for therapeutic interventions aimed at inhibiting aberrant cellular growth.

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.

InChI:InChI=1/C7H19N3/c8-4-1-2-6-10-7-3-5-9/h10H,1-9H2/p+3

124-20-9 Relevant articles

Probing mammalian spermine oxidase enzyme-substrate complex through molecular modeling, site-directed mutagenesis and biochemical characterization

Tavladoraki, Paraskevi,Cervelli, Manuela,Antonangeli, Fabrizio,Minervini, Giovanni,Stano, Pasquale,Federico, Rodolfo,Mariottini, Paolo,Polticelli, Fabio

, p. 1115 - 1126 (2011)

Spermine oxidase (SMO) and acetylpolyami...

Mechanistic and structural analyses of the roles of active site residues in yeast polyamine oxidase Fms1: Characterization of the N195A and D94N enzymes

Adachi, Mariya S.,Taylor, Alexander B.,Hart, P. John,Fitzpatrick, Paul F.

, p. 8690 - 8697 (2012)

Flavoprotein Fms1 from Saccharomyces cer...

Mechanistic studies of human spermine oxidase: Kinetic mechanism and pH effects

Adachi, Mariya S.,Juarez, Paul R.,Fitzpatrick, Paul F.

, p. 386 - 392 (2010)

In mammalian cells, the flavoprotein spe...

A lysine conserved in the monoamine oxidase family is involved in oxidation of the reduced flavin in mouse polyamine oxidase

Henderson Pozzi, Michelle,Fitzpatrick, Paul F.

, p. 83 - 88 (2010)

Lysine 315 of mouse polyamine amine oxid...

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Jackson

, p. 1374 (1956)

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Preparation method of spermidine

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Paragraph 0032-0037, (2021/12/07)

The invention relates to the technical f...

Synthesis process of spermidine and intermediate thereof

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Paragraph 0054-0059, (2021/10/27)

The invention provides a synthesis proce...

Method for preparing spermidine

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Paragraph 0057; 0072-0074, (2019/01/14)

The invention belongs to the field of ch...

124-20-9 Process route

1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride
117654-79-2

1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
2: spermine oxidase / pH 9.5 / Enzymatic reaction
With recombinant human polyamine oxidase; spermine oxidase;
1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride
117654-79-2

1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride

N-(3-aminopropyl)-1,4-diaminobutane
124-20-9

N-(3-aminopropyl)-1,4-diaminobutane

Spermine
71-44-3

Spermine

benzylamine
100-46-9

benzylamine

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
2: recombinant human polyamine oxidase / pH 9.5 / Enzymatic reaction
With recombinant human polyamine oxidase;

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