17407-37-3

Usage

Uses

dl-α-Tocopherol Succinate is the racemic analog of α-Tocopheryl Succinate (T539950), 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.

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)

Upstream product

• 502-69-2 6,10,14-Trimethyl-2-pentadecanon 
• 1117-52-8 6,10,14-trimethyl-5,9,13-pentadecatriene-2-on 
• 505-32-8 isophytol 
• 108-30-5 succinic acid anhydride 
• 59-02-9 vitamin E 

Relevant academic research and scientific papers

Covalent and Ionic Conjugates of Trolox and α-Tocopherol with 1-Aminoadamantane

Covalent, ionic, and ionic-covalent conjugates of trolox and α-tocopherol with 1-aminoadamantane were synthesized. Their structures were elucidated using mass spectrometry and IR, PMR, and 13C NMR spectroscopy. The water solubility of the ionic trolox conjugates with 1-aminoadamantane increased by 2–24 times as compared with that of trolox whereas that of the α-tocopherol succinate conjugates remained the same as that of α-tocopherol.

Design and Synthesis of Polymer Prodrugs for Improving Water-Solubility, Pharmacokinetic Behavior and Antitumor Efficacy of TXA9

Purpose: TXA9, a novel cardiac glycoside, has a potent anti-proliferative effect against A549 human lung cancer cells, however, possesses a poor water-solubility and a rapid metabolic rate in vivo which limited the further development of TXA9. To overcome the shortcomings of TXA9, four polymer prodrugs of TXA9 were designed and synthesized. Methods: Poly (ethylene glycol) monomethyl ether (mPEG) and α-tocopherol polyethylene glycol succinate (TPGS) were applied to modify TXA9 via carbonate ester and glycine linkers respectively to obtain four polymer prodrugs. The water-solubility and stability of prodrugs were studied in vitro while their pharmacokinetic behaviors and antitumor activity were investigated in vivo. Results: The water-solubility of TXA9 was obviously increased and prodrugs with glycine linkers showed a better stability in rat plasma. Their pharmacokinetic investigation found that the t1/2 and AUC0-∞ of TPGS-Gly-TXA9 was increased by 80- and 9.6-fold compared with that of TXA9, which was more superior than the other three prodrugs. More importantly, the tumor inhibition rate of TPGS-Gly-TXA9 (43.81%) on A549 xenograft nude mice was significantly increased compared with that of TXA9 (25.26%). Conclusion: The above results suggested that TPGS-Gly-TXA9 possessed better antitumor efficiency than TXA9 and could be further investigated as an anti-cancer agent.

Green preparation method of isoxazole compound participating in water-soluble vitamin E

The invention provides a green synthesis method of an isoxazole compound represented by the formula (III), wherein the aldehyde oxime compound represented by the formula (I) is a substrate and is in an aqueous solution of a surfactant with a mass concentration 1 wt % - 5 wt % in N - chlorosuccinimide. The alkyne compound represented by the formula (II) is reacted 6 - 16h at room temperature under the common action of the basic substance, and the resulting reaction solution is post-treated to obtain the isoxazole compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

Preparation method of water-soluble vitamin E participated conjugated diyne compound

The water-soluble vitamin E participates in the green preparation method of the conjugated diyne compound, the water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized. The excellent physicochemical properties of water are fully utilized, the reaction conditions are mild and efficient, the surfactant TPGS - 750 - M can be recycled through treatment, and the principle of environmental friendliness is completely met. The reaction substrate is wide in applicability, can catalyze the aryl alkyne, can catalyze the aliphatic hydrocarbon, and provides a simple and environment-friendly preparation method for the synthesis of the conjugated diyne. The copper catalyst which is more suitable for the reaction and reaction medium of the invention is screened out, and the yield is greatly improved.

Preparation method for high-purity tocopherol succinate salt

The invention relates to the field of organic synthesis, specifically to a preparation method for tocopherol succinate salt. The preparation method for the tocopherol succinate salt provided by the invention comprises the following steps: hydrogenating dl-alpha-tocopherol in the presence of a precious metal catalyst, subjecting a hydrogenated product and succinic anhydride to an esterification reaction in the presence of alkali so as to prepare a tocopherol succinate intermediate; and subjecting the tocopherol succinate intermediate to salt-forming. The preparation method for the tocopherol succinate salt provided by the invention can effectively improve the purity of a target product, can effectively reduce the content of a single impurity, and can prepare a calcium salt product with a purity capable of reaching 99.9% or above.

New propanoyloxy derivatives of 5β-cholan-24-oic acid as drug absorption modifiers

A series of final twelve propanoyloxy derivatives of 5β-cholan-24-oic acid (O-propanoyl derivatives of cholic acid) as potential drug absorption modifiers (skin penetration enhancers, intestinal absorption promoters) was generated by multistep synthesis. Structure confirmation of all generated compounds was accomplished by 1H NMR, 13C NMR, IR and MS spectroscopy methods. All the prepared compounds were analyzed using RP-TLC, and their lipophilicity (RM) was determined. The hydrophobicity (log P), solubility (log S), polar surface area (PSA) and molar volume (MV) of the studied compounds were also calculated. All the target compounds were tested for their in vitro transdermal penetration effect and as potential intestinal absorption enhancers. The cytotoxicity of all the evaluated compounds was evaluated against normal human skin fibroblast cells. Their anti-proliferative activity was also assessed against human cancer cell lines: T-lymphoblastic leukemia cell line and breast adenocarcinoma cell line. One compound showed selective cytotoxicity against human skin fibroblast cells and another compound possessed the highest cytotoxicity against all the tested cell lines. Only one compound expressed anti-proliferative effect on leukemia cancer cells without affecting the growth of normal cells, which should be promising in potential development of new drugs. Most of the target compounds showed minimal anti-proliferative activity (IC50 > 37 μM), indicating they would have moderate cytotoxicity when administered as chemical absorption modifiers. The relationships between the lipophilicity/polarity and the chemical structure of the studied compounds as well as the relationships between their chemical structure and enhancement effect are discussed in this article.

TPGS-750-M: A second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature

An environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-coupling reactions in water. Several "name" reactions, including Heck, Suzuki-Miyaura, Sonogashira, and Negishi-like couplings, have been studied using this technology, as have aminations, C-H activations, and olefin metathesis reactions. Physical data in the form of DLS and cryo-TEM measurements suggest that particle size and shape are key elements in achieving high levels of conversion and, hence, good isolated yields of products. This new amphiphile will soon be commercially available.

Surfactant Compositions and Synthesis

Disclosed herein are environmentally benign surfactants including TPGS-550-M, TPGS-750-M and TPGS-1000-M that comprises of diesters composed of racemic α-tocopherol, MPEG-550, MPEG-750 and MPEG-1000, respectively, and a succinic acid fragment. Also disclosed are novel and efficient methods for their synthesis. The surfactants are designed as an effective nanomicelle-forming species for dissolution of hydrophobic compounds and composition and for general use in metal-catalyzed cross-coupling reactions in water.

SUBMICRON NANOPARTICLE OF POORLY WATER SOLUBLE CAMPTOTHECIN DERIVATIVES AND PROCESS FOR PREPARATION THEREOF

The present invention relates to a nanoparticle composition comprising a camptothecin derivative, solid polyethyleneglycol and an anti-associative agent, and the process for preparing the same. Specifically, the present invention provides a composition comprising a nanoparticle of the camptothecin derivative, which is prepared by solid-dispersing the poorly water soluble camptothecin derivative in polyethyleneglycol and dissolving the solid dispersions in an aqueous solution containing an anti-associative agent. The composition of the present invention stabilizes the camptothecin derivative lactone form in body fluid for effective anticancer activity.

Polyphenolic Bioprecursors

Cosmetic and therapeutic, in particular dermatological bioprecursors have the formula [A]n—PP—[B]m wherein PP is a polyphenol radical in which each hydroxyl function is protected by a group A or a group B, A is a saturated or unsaturated, substituted or unsubstituted alkyl radical having 1 to 20 carbon atoms which is bonded to the polyphenol, n is an integer not less than 1, and B is a precursor of a biologically active molecule, which is also bonded to the polyphenol, and m is an integer also not less than 1.