d-alpha-Tocopheryl acid succinate

Base Information

• Chemical Name: d-alpha-Tocopheryl acid succinate
• CAS No.: 17407-37-3
• Molecular Formula: C33H54 O5
• Molecular Weight: 530.789
• European Community (EC) Number: 241-433-7
• NSC Number: 173849
• DSSTox Substance ID: DTXSID90859862
• Nikkaji Number: J24.825H
• Metabolomics Workbench ID: 46157
• ChEMBL ID: CHEMBL3561966
• Mol file: 17407-37-3.mol

Synonyms:3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1-benzopyran-6-ol;Acetate, Tocopherol;alpha Tocopherol;alpha Tocopherol Acetate;alpha Tocopherol Hemisuccinate;alpha Tocopherol Succinate;alpha Tocopheryl Calcium Succinate;alpha-Tocopherol;alpha-tocopherol acetate;alpha-tocopherol hemisuccinate;alpha-tocopherol succinate;alpha-Tocopheryl Calcium Succinate;d alpha Tocopherol;d alpha Tocopheryl Acetate;d-alpha Tocopherol;d-alpha-Tocopheryl Acetate;R,R,R-alpha-Tocopherol;Tocopherol Acetate;Tocopherol Succinate;Tocopherol, d-alpha;Tocopheryl Acetate;vitamin E succinate

Chemical Property of d-alpha-Tocopheryl acid succinate

Chemical Property:

• Vapor Pressure: 1.58E-16mmHg at 25°C
• Melting Point: 68-71 °C
• Refractive Index: 1.498
• Boiling Point: 625.8°Cat760mmHg
• PKA: 4.35±0.17(Predicted)
• Flash Point: 187°C
• PSA: 72.83000
• Density: 1.002g/cm³
• LogP: 8.90480
• XLogP3: 10.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 530.39712482
• Heavy Atom Count: 38
• Complexity: 720

Purity/Quality:

99%, ^*data from raw suppliers

dl-α-TocopherolSuccinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C(C2=C1OC(CC2)(C)CCCC(C)CCCC(C)CCCC(C)C)C)OC(=O)CCC(=O)O)C
• 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.

Technology Process of d-alpha-Tocopheryl acid succinate

There total 7 articles about d-alpha-Tocopheryl acid succinate 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: 100.0%

succinic acid anhydride (108-30-5) + vitamin E (59-02-9,18920-62-2) → vitamin E succinate (17407-37-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1007/s11095-020-02789-w

Reference yield:

isophytol (505-32-8) → vitamin E succinate (17407-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) chloride / acetic acid butyl ester / 110 - 129 °C

2: triethylamine / toluene / 6 h / 20 - 60 °C / 2250.23 Torr

With triethylamine; zinc(II) chloride; In acetic acid butyl ester; toluene;

Reference yield:

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on (1117-52-8) → vitamin E succinate (17407-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium on activated charcoal; hydrogen / isopropyl alcohol / 3 h / 100 °C

2: 2 h / 0 - 5 °C / Inert atmosphere

3: zinc(II) chloride / acetic acid butyl ester / 110 - 129 °C

4: triethylamine / toluene / 6 h / 20 - 60 °C / 2250.23 Torr

With palladium on activated charcoal; hydrogen; triethylamine; zinc(II) chloride; In acetic acid butyl ester; isopropyl alcohol; toluene;

upstream raw materials:

succinic acid anhydride

vitamin E

isophytol

6,10,14-trimethyl-5,9,13-pentadecatriene-2-on

Refernces

• 1、 Cai, Chengcheng,Han, Na,Li, Yiwen,Liu, Zhihui,Ye, Chun,Yin, Jun,Zhai, Jianxiu,Zhao, Meng. "Design and Synthesis of Polymer Prodrugs for Improving Water-Solubility, Pharmacokinetic Behavior and Antitumor Efficacy of TXA9". . . Retrieved 2020.
• 2、 -. "Preparation method of water-soluble vitamin E participated conjugated diyne compound". Paragraph 0031-0033. . Retrieved 2021/11/14.