Spermine

Base Information

• Chemical Name: Spermine
• CAS No.: 71-44-3
• Deprecated CAS: 115-04-8,1127437-73-3,1127437-73-3
• Molecular Formula: C10H26N4
• Molecular Weight: 202.343
• Hs Code.: 29212900
• European Community (EC) Number: 200-754-2
• NSC Number: 268508
• UNII: 2FZ7Y3VOQX
• DSSTox Substance ID: DTXSID9058781
• Nikkaji Number: J5.246I
• Wikipedia: Spermine
• Wikidata: Q424597
• NCI Thesaurus Code: C106406
• Pharos Ligand ID: 9A2KG497S5ZP
• Metabolomics Workbench ID: 37686
• ChEMBL ID: CHEMBL23194
• Mol file: 71-44-3.mol

Synonyms:Spermine

Chemical Property of Spermine

Chemical Property:

• Appearance/Colour: white to slightly off-white powder crystal
• Vapor Pressure: 0.000683mmHg at 25°C
• Melting Point: 310-311 °C (dec.)(lit.)
• Refractive Index: 1.4850 (estimate)
• Boiling Point: 308.4 °C at 760 mmHg
• PKA: 10.88±0.19(Predicted)
• Flash Point: 175.6 °C
• PSA: 76.10000
• Density: 0.925 g/cm³
• LogP: 1.82580
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: Soluble in chloroform, methanol, water and lower alcohols. Insoluble in ether, benzene and petroleum ether.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 202.21574685
• Heavy Atom Count: 14
• Complexity: 86.1

Purity/Quality:

98%,99%, ^*data from raw suppliers

Spermine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,C
• Hazard Codes: Xi,C
• Statements: 36/38-34
• Safety Statements: 26-36-45-36/37/39-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C(CCNCCCN)CNCCCN
• Recent ClinicalTrials: Prenatal Administration of Spermine Promotes Maturation of Premature Fetal Gut Epithelial Tight Junction: Experimental Study on Fetal Rabbit
• Description: Spermine is an endogenous polyamine synthesized from the reaction of spermidine with decarboxylated S-adenosylmethionine in the presence of the enzyme spermine synthase and is required for eukaryotic cell growth and protein synthesis. Intracellular spermine blocks inward rectifying K+ channels, whereas extracellular spermine acts as a mixed NMDA glutamate receptor agonist/antagonist at the polyamine site. Spermine has neuroprotective and anti-inflammatory effects and functions as a free radical scavenger to prevent DNA damage by reactive oxygen species.
• Uses: immune modulator Binds to the polyamine modulatory site of NMDA Spermine is essential for both normal and neoplastic tissue growth. It is involved in the modulation of calcium-dependent immune processes. It plays an important role in cellular proliferation and differentiation as well as inhibits neuronal nitric oxide synthase (nNOS). Biogenic polyamine formed from spermidine and occurring in almost all tissues. Essential for both normal and neoplastic tissue growth. Involved in the modulation of calcium-dependent immune processes

Technology Process of Spermine

There total 25 articles about Spermine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride (117654-79-2) → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + benzylamine (100-46-9)

Guidance literature:

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;

DOI:10.1007/s00726-009-0429-2

Reference yield:

N1-(3-aminopropyl)-N4-(3-(benzylamino)propyl)butane-1,4-diamine → N-(3-aminopropyl)-1,4-diaminobutane (124-20-9) + Spermine (71-44-3) + benzylamine (100-46-9) + N-{3-[(4-aminobutyl)amino]propyl}(phenylmethyl)amine

Guidance literature:

With recombinant human polyamine oxidase; pH=9.5; pH-value; Reagent/catalyst; Kinetics; Enzymatic reaction;

DOI:10.1007/s00726-009-0429-2

Reference yield:

3,3′,3″,3′″-(butane-1,4-diylbis(azanetriyl))tetrapropanenitrile → Spermine (71-44-3) + N,N,N',N'-tetra(3-aminopropyl)-1,4-butanediamine (120239-63-6) + N,N,N'-tris(3-aminopropyl)-1,4-butanediamine

Guidance literature:

With ammonia; hydrogen; In tetrahydrofuran; at 50 ℃; under 33753.4 Torr; Autoclave;

upstream raw materials:

3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile

1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane

kinetin

(R)-(-)-abscisic acid

Downstream raw materials:

ethyl 16-amino-3-(4-methoxyphenyl)-4,8,13-triazahexadecanoate

philanthotoxin-343

1,1'-(butane-1,4-diyl)-2,2'-diphenylbis(hexahydropyrimidine)

N¹,N¹⁴-bis(triphenylmethyl)spermine

Refernces

• 1、 -. "Process for the preparation of N,N,N',N'-tetrakis(3-aminopropyl)-1,4-butanediamine". Paragraph 0022-0026. . Retrieved 2013/03/26.
• 2、 Haekkinen, Merja R.,Hyvoenen, Mervi T.,Auriola, Seppo,Casero Jr., Robert A.,Vepsaelaeinen, Jouko,Khomutov, Alex R.,Alhonen, Leena,Keinaenen, Tuomo A.. "Metabolism of N-alkylated spermine analogues by polyamine and spermine oxidases". experimental part. p. 369 - 381. Retrieved 2010/11/18.