Stabilized derivatives of ascorbic acid.
A technology of carboxylic acids, compounds, used in the field of stabilizing ascorbic acid derivatives and compositions containing the derivatives
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Embodiment
[0062] Synthesis of embodiment 1.2-octanoyl ascorbic acid sodium salt
[0063] Step 1.5, the synthesis of 6-isopropylidenyl (isopropylidenyl) ascorbic acid
[0064] To a suspension of ascorbic acid (20 g (0.114 mol)) in 660 mL of anhydrous acetone was added 20 g (0.125 mol) of anhydrous copper sulfate, and the reaction mixture was stirred at room temperature for 20 h. The process was monitored by TLC (chloroform-methanol-water, 10:10:3). Filtration and evaporation yielded 22.57 g (92%) of 5,6-isopropylidene ascorbic acid.
[0065] Step 2. Synthesis of 2-octanoyl-5,6-isopropylidene ascorbic acid.
[0066] To a solution of 5,6-isopropylidene ascorbic acid (14.5 g, 0.067 mol) in anhydrous pyridine (80 mL), octanoyl chloride (12.0 g, 0.074 mol) was added dropwise at 0°C. The reaction system was stirred at 0°C for 1.5 h, and the process was monitored by TLC (chloroform-methanol, 3:1). Then, ice water (300 mL) was added and the reaction mixture was adjusted to pH 3 with phosphor...
Embodiment 2
[0071] Embodiment 2. Synthesis of 2-palmitoyl ascorbic acid sodium salt
[0072] Step 1. Synthesis of 5,6-isopropylidene ascorbic acid
[0073] 20 g (0.125 mol) of anhydrous copper sulfate was added to a suspension of 20 g (0.114 mol) of ascorbic acid in 660 mL of anhydrous acetone, and the reaction mixture was stirred at room temperature for 20 h. The process was monitored by TLC (chloroform-methanol-water, 10:10:3). Filtration and evaporation yielded 22.57 g (92%) of 5,6-isopropylidene ascorbic acid.
[0074] Step 2. Synthesis of 2-palmitoyl-5,6-isopropylidene ascorbic acid
[0075] To a solution of 5,6-isopropylidene ascorbic acid (14.5 g, 0.067 mol) in anhydrous pyridine (80 mL) was added dropwise palmitoyl chloride (12.0 g, 0.074 mol) at 0°C. The reaction system was stirred at 0°C for 1.5 h, and the process was monitored by TLC (chloroform-methanol, 3:1). Then, ice water (300 mL) was added and the reaction mixture was adjusted to pH 3 with phosphoric acid (-10 mL) and...
Embodiment 3
[0081] Example 3: Dermatological Effects - Ascorbic Acid Derivatives Stimulate Collagen Synthesis in Primary Human Foreskin Fibroblasts
[0082] L-Ascorbic acid stimulates collagen synthesis in cultured human dermal fibroblasts. Ascorbate contributes to several metabolic processes including efficient hydroxylation of hydroxyproline in collagen synthesis.
[0083] In order to evaluate the effect of ascorbic acid derivatives of the present invention on collagen synthesis, cultured human foreskin fibroblasts were put into 24-well microculture plates (microculture plates), and the medium contained 100 μg / ml β-aminopropionitrile, 10 μCi [2,3- 3 H] Proline in DMEM supplemented with 10% fetal calf serum in the presence of ascorbic acid (positive control) or the ascorbic acid derivative of example 1 or 2 at different concentrations, for example from 1 mM to 50 mM. Cultures were incubated for 24 hours. Determination of [2,3- 3 [H]-proline incorporation into salt-precipitated pepsin...
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