4345-03-3 Usage
Description
Tocopherol succinate (4345-03-3) is a potent antioxidant. Protects mice from gamma-radiation by induction of granulocyte-colony stimulating factor.1,2?Tocopherol succinate induces apoptosis in human gastric cancer cells3?and inhibits proliferation of mesothelioma cells by down-regulation of fibroblast growth factor receptor-14. Induces apoptosis in neuroblastoma cells.5
Chemical Properties
Off-White to Pale Yellow Solid
Uses
Different sources of media describe the Uses of 4345-03-3 differently. You can refer to the following data:
1. A potent antioxidant tocopherol
2. A potent novel antineoplastic agent with high selectivity and cooperativity with tumor necrosis factor-related apoptosis-inducing ligand (Apo2 ligand). It inhibits proliferation of mesothelioma cells by selective down-regulation of fibroblast growth factor receptors. Furthermore, it has been shown to enhance the anti-tumor effect of dendritic cell vaccines.
3. A potent novel antineoplastic agent with high selectivity and cooperativity with tumor necrosis factor-related apoptosis-inducing ligand (Apo2 ligand). It inhibits proliferation of mesothelioma cells
by selective down-regulation of fibroblast growth factor receptors. Furthermore, it has been shown to enhance the anti-tumor effect of dendritic cell vaccines.
General Description
White powder.
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Vitamin E succinate is an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Fire Hazard
Flash point data for Vitamin E succinate are not available; however, Vitamin E succinate is probably combustible.
Flammability and Explosibility
Notclassified
Biochem/physiol Actions
Tocopherol exhibits antioxidant property by protecting the cells and membranes from oxidative stress. In plants, high levels of α-tocopherol leads to plant stress tolerance whereas low levels is associated with oxidative stress. In humans, tocopherol prevents cancer, premature aging, atherosclerosis, arthritis caused due to free radicals. Vitamin E succinate (VES) is an anti-tumor analog of vitamin E.
Safety Profile
When heated to
decomposition it emits acrid smoke and
irritating fumes.
References
1) Singh?et al. (2010),?Alpha-tocopherol succinate protects mice from gamma-radiation by induction of granulocyte-colony stimulating factor; Int. J. Radiation Biol.,?86?12
2) Singh?et al. (2009),?Tocopherol succinate: a promising radiation countermeasure; Immunopharmacol.,?9?1423
3) Wu?et al. (2004),?c-Jun N-terminal kinase is required for vitamin E succinate-induced apoptosis in human gastric cancer cells; J. Gastroenterol.,?10?1110
4) Stapelberg?et al. (2004),?alpha-Tocopheryl succinate inhibits proliferation of mesothelioma cells by selective down-regulation of fibroblast growth factor receptors; Biochem. Biophys. Res. Commun.,?318?636
5) Swettenham?et al. (2005),?Alpha-tocopheryl succinate selectively induces apoptosis in neuroblastoma cells: potential therapy of malignancies of the nervous system; J. Neurochem.,?94?1448
Check Digit Verification of cas no
The CAS Registry Mumber 4345-03-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,3,4 and 5 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4345-03:
(6*4)+(5*3)+(4*4)+(3*5)+(2*0)+(1*3)=73
73 % 10 = 3
So 4345-03-3 is a valid CAS Registry Number.
InChI:InChI=1/C33H54O5/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-20-33(8)21-19-28-27(7)31(25(5)26(6)32(28)38-33)37-30(36)18-17-29(34)35/h22-24H,9-21H2,1-8H3,(H,34,35)/t23-,24-,33-/m1/s1
4345-03-3Relevant articles and documents
Synthesis, characterization, and in-vitro antitumor activity of the polyethylene glycol (350 and 1000) succinate derivatives of the tocopherol and tocotrienol isomers of Vitamin E
Abu-Fayyad, Ahmed,Nazzal, Sami
, p. 145 - 156 (2017)
Vitamin E refers to a group of saturated tocopherol (T) isomers and the biologically more active unsaturated tocotrienol (T3) isomers. PEGylated α-tocopherol, commercially known as Vitamin E TPGS, has been used as an emulsifier and therapeutic agent for children with vitamin E deficiency. Limited information, however, is available about the PEG conjugates of the tocotrienol isomers of vitamin E. The current work was therefore undertaken to synthesize and characterize the water soluble polyethylene glycol (PEG 350 and 1000) derivatives of T and T3. Yield and the identity of the synthesized products were confirmed by 1H NMR, mass spectroscopy, HPLC, and thermal analysis. The self-assembly of the PEGylated vitamin E isomers in water at critical micelle concentrations (CMC) was further confirmed by size, zeta, and Cryo-TEM image analysis. While stable at pH 7.4, PEG conjugates were found to rapidly hydrolyze at pH 1.2. Our data showed that PEGylated T3 isomers were significantly more active as inhibitors for P-glycoprotein than PEGylated T. The in vitro cytotoxicity of the conjugates was also tested against a large panel of normal and tumorigenic cells. Of the conjugates, γ-T3PGS 1000 and δ-T3PGS 1000 were found to have the least toxicity against non-tumorigenic breast and pancreatic cell lines, which may be advantageous for its use as functional excipients in drug delivery. The results from the current work have demonstrated the feasibility of synthesizing PEGylated conjugates of vitamin E isomers and highlighted the potential use of these conjugates in drug delivery as functional and safer excipients especially for γ-T3PGS 1000 and δ-T3PGS 1000 conjugate.
Encapsulation of enzymes in metal ion-surfactant nanocomposites for catalysis in highly polar solvents
Cao, Xun,Ni, Yan,Zhang, Alei,Xu, Sheng,Chen, Kequan,Ouyang, Pingkai
, p. 3134 - 3137 (2017)
We described a method to encapsulate enzymes in metal ion-surfactant nanocomposites. The nanobiocatalyst displayed highly retained activity (～100%) and much improved stability in protein-denaturing organic solvents. As a demonstration, the encapsulated lipase exhibited much higher activity and stability in the synthesis of vitamin E succinate in dimethyl sulfoxide.
Method for reducing by hydrolysis producing high content of natural vitamin E industrial production method
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Paragraph 0039-0040, (2017/03/08)
An industrialized production method for producing high-content natural vitamin E by utilizing a hydrolysis reduction process comprises: (1) dissolving low-content natural mixed tocopherols in proper amount of a solvent, adding succinic anhydride and performing esterification reaction under an alkaline condition, so as to generate corresponding natural tocopherol esters; (2) performing reduced-pressure distillation on the product obtained in the step (1) to remove the solvent, adding an extraction reagent and performing extraction, water washing, crystallization and separation, so as to obtain natural tocopherol succinate with high content; (3) hydrolyzing natural tocopherol succinate obtained in the step (2) under an alkaline condition, and reducing to generate natural tocopherols; and (4) performing extraction, water washing, separation and distillation on the natural tocopherols obtained through hydrolysis in the step (3), so as to obtain the natural vitamin E (mixed tocopherols) with the high content up to 90% or more.
