Stamatov, Stephan D. Chemistry and physics of lipids 91.2 (1998): 129-134.
This study describes a three-step synthesis of DL-α-tocopheryl-6-O-phosphorylcholine and its -6-O-phosphorylethanolamine homologue. The synthesis pathway involves the conversion of DL-α-tocopherol to the corresponding 2-bromoethyl phosphate, hydrolysis of the remaining phosphorochloridate bond, and treatment of the resulting diester intermediate with aqueous trimethylamine or ammonia to yield the aminated target derivatives, with overall yields ranging from 61% to 67%.
Synthesis of DL-α-Tocopheryl-6-O-Phosphorylcholine (4a)
To a solution of 2-bromoethyl dichlorophosphate (1; 0.94 g, 3.9 mmol) and triethylamine (1.62 g, 16.0 mmol) in benzene (100 mL), DL-α-tocopherol (2; 1.29 g, 3.0 mmol), dissolved in benzene (20 mL), was added dropwise. The reaction was stirred at room temperature (20-25°C) for 24 hours. The precipitated triethylammonium chloride was filtered off. Hydrolysis of the remaining phosphorochloridate bond and excess 2-bromoethyl dichlorophosphate (1) was carried out by adding water (40 mL) while stirring the mixture at 20-25°C for 12 hours. The organic phase was separated, washed with water (3×40 mL), and the solvent was removed under vacuum. The residue was dissolved in a mixture of chloroform/2-propanol/dimethylformamide (100 mL, 3:5:5, v/v/v) and treated with a 30% solution of triethylamine in water (30 mL, 0.15 mol) at 20-25°C for 24 hours. After removing the volatile solvents under vacuum at 40-45°C, the crude product (4a) was extracted with chloroform/methanol (3:1, v/v) (3×60 mL) from the residual water/dimethylformamide mixture. The extracts were combined, washed with water (3×50 mL), dried over anhydrous sodium sulfate, filtered, and the solvents were removed as previously described. The semi-solid residue was dissolved in system A (20 mL), and the target compound (4a) was isolated by column chromatography in pure form.
Synthesis of DL-α-Tocopheryl-6-O-Phosphorylethanolamine (4b)
Starting with DL-α-tocopherol (2; 1.29 g, 3.0 mmol), the crude diester phosphate (3) was obtained using the procedure described for (4a). The product was dissolved in a mixture of chloroform/2-propanol/dimethylformamide (120 mL, 1:2:5, v/v/v) and treated with a 25% solution of ammonia in water (90 mL, 1.32 mol) at 20-25°C for 48 hours. After removing the volatile solvents under vacuum at 40-45°C, the target compound (4b) was extracted with chloroform/methanol (3:1, v/v) (3×80 mL) from the residual water/dimethylformamide mixture and purified following the same procedure used for (4a).
What is the product name of CAS number 10191-41-0?
The product name is Dl-Alpha-Tocopherol.
What are the synonyms for Dl-Alpha-Tocopherol?
The synonyms are Dl-Α-Tocopherol.
What is the molecular weight of Dl-Alpha-Tocopherol?
The molecular weight is 430.71.
What is the molecular formula of Dl-Alpha-Tocopherol?
The molecular formula is C29H50O2.
What is the percentage of actives in Dl-Alpha-Tocopherol?
The percentage of actives is 95%.
What is the physical state of Dl-Alpha-Tocopherol?
The physical state is a liquid.
What are the typical applications of Dl-Alpha-Tocopherol?
It is typically used as an antioxidant.
How is Dl-Alpha-Tocopherol commonly used in products?
It is commonly used to extend the shelf life of products.
What is the significance of the CAS number 10191-41-0 in relation to Dl-Alpha-Tocopherol?
The CAS number is a unique identifier for chemical compounds, in this case, for Dl-Alpha-Tocopherol.
How does Dl-Alpha-Tocopherol play a role in maintaining product quality?
Dl-Alpha-Tocopherol acts as an antioxidant, helping to preserve the quality and freshness of products.
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