Formulations of water-soluble derivatives of vitamin E and compositions containing same

A composition and derivative technology, applied in the field of vitamin E water-soluble derivative preparations and compositions containing the same, can solve the problems of non-polar compound amount or concentration limitation, undesired sensory properties and the like

Inactive Publication Date: 2016-01-06
VIRUN INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Furthermore, the amount or concentration of non-polar compounds in existing food and beverage products is l...

Method used

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  • Formulations of water-soluble derivatives of vitamin E and compositions containing same
  • Formulations of water-soluble derivatives of vitamin E and compositions containing same
  • Formulations of water-soluble derivatives of vitamin E and compositions containing same

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[0338] Described herein are methods of preparing water-soluble vitamin E derivative mixtures (compositions) such as TPGS compositions described herein, e.g., preparing water-soluble vitamin E derivative compositions such as comprising less than 70% by weight of TPGS monomer and more than TPGS composition of 12 wt% TPGS dimer. Existing methods for the preparation of vitamin E derivatives can be used, but modified to produce higher concentrations of the dimeric form by adjusting the reaction conditions. Such adjustments can be determined empirically as necessary, for example, by varying reaction parameters (eg, time, temperature, and reactant concentrations) to determine conditions that favor higher levels of dimer formation.

[0339] A water-soluble vitamin E derivative mixture (e.g., a TPGS monomer-dimer mixture) prepared according to the method may comprise: 25% to 69% by weight or about 25% to 69% by weight monomer, for example at or about 25% by weight, 26% by weight, 27% ...

Embodiment 1

[0774] Method for preparing TPGS compositions

[0775]d-alpha-tocopheryl polyethylene glycol 1000 succinate (TPGS1000) was synthesized from vitamin E succinate according to the following general procedure.

[0776] Polyethylene glycol (PEG) 1000 (168.7 kg) was added to a reaction flask containing 1430 L of toluene, followed by 71.5 kg vitamin E (alpha-tocopheryl acid) succinate and 2.86 kg p-toluenesulfonic acid. The reaction mixture was heated to 110°C to 112°C and refluxed for up to 6.5 hours, water formed during the esterification reaction was removed by azeotropic distillation. The reaction was terminated when the desired amounts of TPGS monomer and TPGS dimer were formed (indicated by high performance liquid chromatography (HPLC) and thin layer chromatography (TLC)), resulting in the TPGS compositions shown in Table 1 below. Each of the TPGS compositions in Table 1 was formed by terminating the reaction at different time points and contained various amounts of TPGS monom...

Embodiment 2

[0794] Evaluation of Clarity of TPGS-Containing Compositions by Turbidity Analysis

[0795] The clarity of the TPGS compositions prepared above was evaluated by turbidity analysis. TPGS Compositions 1-11 were formulated as 1 g concentrate, each dissolved in 8 oz of water. Then, the clarity of the resulting aqueous liquid dilution composition was evaluated by measuring turbidity using a nephelometer. The evaluation results are shown in Table 2 below.

[0796] Each of the eleven TPGS compositions listed in Table 1 above was diluted in water (purified according to the provided method) using the following procedure.

[0797] by putting The beaker was placed on a Thermolyne heating plate (Model #846925) and 8 ounces of water was heated in the beaker until the water reached 49.8°C. Then, add the TPGS composition concentrate to the hot water and stir with a stir bar until dispersed. The resulting aqueous TPGS composition was cooled to room temperature (about 25°C). For evaluat...

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Abstract

Provided herein are compositions that contain water-soluble vitamin E derivative mixtures (compositions), such as tocopheryl polyethylene glycol succinate (TPGS), TPGS analogs, TPGS homo logs and TPGS derivatives. The water-soluble vitamin E mixtures contain mixtures of dimers and monomers of the vitamin E derivative. Also provided are products containing the water-soluble vitamin E derivative mixtures, including concentrates for dilution into aqueous beverages and compositions for direct ingestion.

Description

[0001] related application [0002] U.S. Provisional Application No. 61 / 852,243 to Philip J. Bromley, filed March 15, 2013, entitled "FORMULATIONSOFPEG-DERIVATIVESOFVITAMINEANDCOMPOSITIONSCONTAININGSAME" and filed August 8, 2013 to Philip J. Bromley, entitled "FORMULATIONSOFWATER- Priority benefit is claimed in U.S. Provisional Application No. 61 / 863,732 of SOLUBLEDERIVATIVESOFVITAMINEANDCOMPOSITIONSCONTAININGSAME". Where permitted, the subject matter of each of the above-cited applications is incorporated by reference in its entirety. [0003] This application is related to Philip J. Bromley's US Patent Application (Attorney Docket No. 33312.05741.US01 / 5741), filed on the same date as this case, entitled "FORMULATIONSOFWATER-SOLUBLEDERIVATIVESOFVITAMINEANDCOMPOSITIONSCONTAININGSAME." [0004] This application is related to Philip J. Bromley's US Provisional Application No. 61 / 863,897, filed August 8, 2013, entitled "COMPOSITIONS CONTAINING WATER-SOLUBLE DERIVATIVE SO F VITAMIN...

Claims

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Application Information

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IPC IPC(8): A23L33/10A23L2/52A61K9/00A61K31/355A61K9/107A23L33/15
CPCA23L2/385A23L2/52A61K45/06A61K9/1075A61K31/355A61K31/765A61K47/46A23L2/04A61K36/82A61K35/60A61K36/02A23L33/105A23L33/12A23L33/15A23L33/175A61P25/20A61P25/24A61P3/02A61K2300/00
Inventor P·J·布罗姆利
Owner VIRUN INC
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