Applications of Vitamin C Phosphate_Industrial Additives

Background and overview^[1]

Vitamin C phosphate is one of the Vc derivatives. Compared with Vc, it has strong antioxidant properties and strong thermal stability. It is decomposed into free L-ascorbic acid by phosphate hydrolase in the body and plays a role. Therefore, it can Meet the needs of feed processing and production. So far, there are two main methods for Vc phosphorylation: one is the phosphorylation of phosphorus oxychloride, using L-ascorbic acid as the raw material, and performing a ketal reaction with acetone to generate 5,6-oxy-isopropylidene-L~ Ascorbic acid protects the hydroxyl groups at positions 5 and 6; then dissolve it with pyridine, adjust the pH with potassium hydroxide, add phosphorus oxychloride dropwise to react, evaporate the pyridine, remove salt several times, concentrate, and then perform cationic resin exchange. The eluate is collected, magnesium hydroxide is added for reaction, and finally the low carbon alcohol is crystallized, filtered and dried to complete. The product is mainly L-ascorbic acid-2-monophosphate, and the by-products are mainly L-ascorbic acid-3-phosphate and 2-pyrophosphate. The whole process is complicated and requires a lot of organic solvents, which will cause environmental pollution. The second method is to use phosphate for phosphorylation, and the main product obtained is L-ascorbic acid-2-polyphosphate.

Apply^[2]

Whitening cosmetics have become a type of functional cosmetics that has been hotly researched on Bayer curing agents in the field of cosmetics in recent years. Vitamin C was first considered by dermatologists as a safe oral drug that can lighten spots. Its derivative, vitamin C phosphate, not only has a good whitening effect, but is also chemically stable and non-irritating to the skin. This type of whitening agent is the most popular in China. It is widely used in cosmetics and has been recognized by the public. Foreign research on the application of vitamin C phosphate derivatives in cosmetics is very active.

Vitamin C phosphate derivative can promote collagen synthesis, inhibit collagen decomposition, and improve skin aging. Through research, it was found that sodium vitamin C phosphate can eliminate acne. Vitamin C phosphate salt can promote the synthesis of ceramides on the skin, increase skin softness, moisture, and anti-aging. Vitamin C phosphate is also often formulated with other active ingredients. A cosmetic formula used to eliminate skin pigmentation containing hydroquinone and a salt of vitamin C phosphate, such as magnesium vitamin C phosphate or sodium vitamin C phosphate. Cosmetic formulas containing sodium vitamin C phosphate and zinc oxide. Through comparative experiments, it was found that zinc oxide can improve the stability of sodium vitamin C phosphate in cosmetics. A whitening formula consisting of white blood cell extract and other whitening agents, such as vitamin C magnesium phosphate, vitamin C glucoside, etc. Many cosmetics companies have developed whitening products with vitamin C phosphate derivatives as active ingredients, such as IwaseCosf’s FineDowder C.P.M. product, MaryKay’s whitening foundation milk SPF15, and Marubi’s vitamin C phosphate whitening and anti-yellowing essence. The following lists the formulas of whitening cosmetics:

Preparation^[3]

Method 1: A method for preparing vitamin C phosphate, characterized in that the process steps are: add vitamin C, anhydrous calcium chloride and deionized water into a reaction kettle at 0~5°C, stir until The material liquid is in a suspended state, then slowly add Ca(OH)2 solution dropwise until the pH is 4.5~6.5, then add sodium trimetaphosphate, continue to add calcium hydroxide solution dropwise until the pH is 8~10.5, stir until it becomes viscous. Directly add NaOH solution dropwise to pH 10-13 at a feed liquid temperature of 10-25°C, stir and react for 5-30 minutes, and then spray dry.

Method 2: Preparation method of vitamin C phosphate:

1) Preparation of 5,6-O-isopropylidene-L-ascorbic acid (IPAA)

Add vitamin C, acetone, and POCl3 into the reaction bottle at the ratio of 1g:4.5~5.5mL:0.1~0.3mL, stir and react at 20°C for 4 hours, filter under reduced pressure, and the filter cake is White yellowish solid, wash the filter cake with a small amount of ethyl acetate to remove yellow impurities to obtain white powdery solid 5,6-O-isopropylidene-L-ascorbic acid (IPAA).

2) Synthesis of magnesium L-ascorbic acid-2-phosphate[7-10]

Add a certain amount of distilled water and pyridine into a 250mL four-necked flask, cool to 0~10°C in an ice-salt bath, and pass through nitrogen. Add 0.012 mol of IPAA, add a certain amount of 10 mol/LKOH solution after dissolution, adjust the pH to 12 to 13, and drop 0.020 mol of phosphorus oxychloride evenly under stirring. After the dropwise addition of POCl3 is completed, continue the reaction for 0.5 to 1 hour. After the reaction is completed, a reaction solution containing L-ascorbic acid-2-phosphate without deprotection is obtained. Add 30% MgCl2·6H2O solution to the reaction solution while stirring, filter out the solid with suction, add 35% hydrochloric acid to adjust the pH to 0.5, continue to add a large amount of absolute ethanol, filter with suction, and distill away the ethanol under reduced pressure. Dilute the residual solution with 1 to 2 times the volume of distilled water and place it at room temperature for 2 hours to hydrolyze and remove the protecting group. The white or light yellow powdery product L-ascorbic acid-2-magnesium phosphate is obtained.