CAS number：86404-04-8
molecular formula：C8H12O6
molecular weight：204.18
EINECS number：617-849-3

English synonyms

3-O-Ethyl Ascorbyl Ether;3-O-Ethyl-L-ascorbic Acid;ETHYL ASCORBIC ACID;3-o-ethyl-l-ascorbic acid;3-O-ETHYLASCORBICACID;(5R,1'S)-5-(1,2-Dihydroxy-ethyl)-4-ethoxy-3-hydroxy-5H-furan-2-one;(5r)-5-[(1s)-1,2-dihydroxyethyl]-4-ethoxy-3-hydroxy-5h-furan-2-one;(R)-5-((S)-1,2-dihydroxyethyl)-4-ethoxy-3-hydroxyfuran-2(5H)-one

Related categories

Daily chemical raw materials/cosmetics; cosmetic raw materials; medical raw materials; biochemicals; cosmetic raw materials-whitening agents; chemical raw materials-1; other raw materials; cosmetic daily chemical raw materials; vitamin derivatives; pharmaceutical intermediates; raw materials; cosmetic grades; organic chemicals ;Pharmaceutical raw materials;Pharmaceutical raw materials;Other sugars;APIs;Chemicals;Daily chemical raw materials;Whitening and freckle raw materials;Vitamin C ethyl ether;Intermediates;Chemical intermediates;Cosmetic daily chemical raw materials;Food additives;Cosmetic raw materials whitening raw materials ;Pharmaceutical raw material intermediates; Antioxidants; API; -Pharmaceutical products; chemical raw materials; whitening and lightening; daily chemical raw materials; cosmetic additives; pharmaceuticals, pesticides and dye intermediates; chemical raw materials; fine chemical raw materials; content products; chemical reagents; other categories; nutrition fortifiers; cosmetic functions Raw material additives-VC ethyl ether;new product series;reagents;whitening agent;whitening series;whitening products;reagents for scientific research;Vitamine C derivative;API;86404-04-8;whitening and skin care;reference substance;heterocycle; Organic raw materials; cosmetic whitening products; additives

Introduction

Vitamin C ethyl ether is a very useful vitamin C derivative, it is not only chemically stable, it is a non-discoloring vitamin C derivative, but also a lipophilic, hydrophilic and amphoteric substance, which greatly expands his Scope of application, especially in daily chemical applications. 3-O-ethyl ascorbic acid ether can easily enter the dermis through the stratum corneum. After it enters the body, it is very easy to be decomposed by biological enzymes in the body to exert the biological effect of vitamin C.

Chemical properties

Use

●  Vitamin C ethyl ether (VC ethyl ether) is a lipophilic and hydrophilic amphoteric vitamin C derivative, which not only retains the redox effect of vitamin C but also is very stable. It is a lipophilic and hydrophilic amphoteric substance, which not only makes it extremely convenient to use in the formula, but also makes it easy to penetrate the stratum corneum and enter the dermis layer. After entering the skin, it is easily decomposed by biological enzymes to play the role of vitamin C, thereby improving the its bioavailability.

●  3-O-ethyl ascorbic acid ether (vitamin C ethyl ether) is a substance that dissolves in both oil and water, which allows the formulator to add it into the oil phase or the water phase, or at high or low temperature, so it is convenient to use. More importantly, this amphiphilicity makes it easier to penetrate the stratum corneum and enter the dermis to exert its biological effects, which other vitamin C derivatives do not have. It can block the formation of melanin by inhibiting the activity of tyrosinase; it has whitening and freckle-removing effects (when 2% is added); it resists inflammation caused by sunlight, and has strong antibacterial and anti-inflammatory effects; Skin is radiant and elastic, restores skin cell activity and promotes collagen production.

●  1. Inhibit the activity of tyrosinase by Cu2+ acting on it and block the formation of melanin;
2. Very effective in whitening and freckle removal (when 2% is added);
3. Anti-inflammatory caused by sunlight, has strong antibacterial and anti-inflammatory effects;
4. Improve dull skin and give skin elasticity;
5. Repair skin cell activity and promote collagen production.

Production method

●  1) Synthesis of 5,6-O-isopropylidene-ascorbic acid:
70g of ascorbic acid, 22g of p-toluenesulfonic acid and 700ml of acetone were added to a 1.5-liter single-necked flask, and the reaction was carried out at room temperature (25° C.) for 8 hours, and a large amount of crystals were formed in the reaction solution. After filtering, the filter cake was washed with acetone, and after vacuum drying, 80 g of 5,6-O-isopropylidene-L-ascorbic acid crystals were obtained with a yield of 93%. After supplementing acetone and ascorbic acid, repeat this step to obtain 5,6-O-isopropylidene-L-ascorbic acid in a cycle.
2) Synthesis of 3-O-alkyl-5,6-O-isopropylidene ascorbic acid:
DMSO is the solvent, and the molar ratio of bromoethane to ascorbic acid is 0.5/1: Weigh 30 g of 5,6-O-isopropylidene-L-ascorbic acid, dissolve it in 120 ml of DMSO, add 7.6 g of bromoethane, 11.6 g g sodium bicarbonate, and then react at 70 °C for 2 hours. After cooling to room temperature (25°C), it was extracted three times with 1000 ml of toluene. The extract was washed with water, concentrated and crystallized to obtain 16.2 g of 3-O-ethyl-5,6-O-isopropylidene ascorbic acid. The calculated yield was 95%. Example 10 3-O-ethyl-5,6-O-isopropylidene ascorbic acid deprotection:
3) Synthesis of 3-O-ethyl ascorbic acid:
10 g of 3-O-ethyl-5,6-O-isopropylidene ascorbic acid was dissolved in 100 ml of methanol, then 5 ml (50% by volume) hydrochloric acid was added, and the reaction was heated to 60° C. for 3 hours. After neutralization with sodium bicarbonate, ethyl acetate was added to extract the crystals to obtain 8.2 g of 3-O-ethyl ascorbic acid with a yield of 98%.

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