Database/Antioxidant/Sodium Ascorbyl Phosphate
100% natural origin · ISO 16128

Is Sodium Ascorbyl Phosphate natural?

Yes. The ascorbyl part is glucose-derived and the phosphate and sodium are mineral origin, so the whole salt is natural origin under ISO 16128.

INCI nameSodium Ascorbyl Phosphate
CAS66170-10-3
FormulaC6H6Na3O9P · 322.05 Da
FunctionAntioxidant · Skin Conditioning Agent
FeedstockGlucose-derived ascorbic acid phosphorylated with phosphorus oxychloride or…

How we scored it

What counts. ISO 16128-2 scores the atoms that remain in the final ingredient. Reagents, solvents, catalysts and protecting groups used during manufacture leave no mass behind and are not counted.

Where it comes from

Glucose-derived ascorbic acid phosphorylated with phosphorus oxychloride or trimetaphosphate (mineral phosphorus) and neutralised with sodium hydroxide.

Sodium Ascorbyl Phosphate (SAP) is an ester derivative of L-ascorbic acid (Vitamin C). The synthesis typically involves reacting L-ascorbic acid with a phosphorylating agent in the presence of a base. A common method involves using phosphorus oxychloride (POCl3) or other phosphorus pentahalides as the phosphorylating agent. The reaction is usually carried out in an organic solvent, such as pyridine or a chlorinated hydrocarbon, which acts as both a solvent and a base to neutralize the HCl generated during the reaction. Temperatures are typically kept low, often below 0°C, to control the reaction and prevent degradation of the sensitive ascorbic acid molecule.

Alternatively, milder phosphorylating agents like phosphorus pentoxide (P2O5) in combination with a base, or specific phosphoramidites, can be employed. The choice of solvent and base is critical for achieving good yields and purity. Pyridine is often favored for its ability to act as both a solvent and an acid scavenger. After the phosphorylation reaction is complete, the crude product is typically hydrolyzed to remove any remaining reactive phosphoryl groups and then neutralized with a sodium base, such as sodium hydroxide or sodium carbonate, to form the sodium salt. This step is crucial for the stability and water solubility of the final ingredient.

Purification is a critical step to remove unreacted starting materials, inorganic salts, and byproducts. This often involves a series of steps including extraction, precipitation, washing, and drying. Recrystallization from suitable solvent systems may be employed to achieve high purity. The final product is typically obtained as a white to off-white crystalline powder. The overall process requires careful control of reaction conditions, pH, and temperature to ensure the stability of the ascorbic acid moiety and the desired esterification.

It is important to note that while L-ascorbic acid itself can be produced via fermentation (e.g., the Reichstein process followed by fermentation, or direct fermentation routes), the subsequent esterification to form SAP, and the upstream production of the phosphorylating agents and solvents, are predominantly carried out using petrochemical-derived materials and processes. Therefore, the synthesis of Sodium Ascorbyl Phosphate is considered to be of petrochemical origin.

In plain English

Sodium Ascorbyl Phosphate is a stable, water-soluble derivative of Vitamin C (ascorbic acid). It's often used in skincare products because it acts as a powerful antioxidant, helping to protect the skin from damage caused by free radicals, which are unstable molecules that can contribute to premature aging. It's also known for its potential to brighten the skin and improve the appearance of uneven skin tone.

CosIng definition: L-Ascorbic acid, 2-(dihydrogen phosphate), trisodium salt

Structure

2D structure of Sodium Ascorbyl Phosphate

trisodium;[(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-oxido-5-oxo-2H-furan-4-yl] phosphate

PubChem CID 10990876 ↗

References

  1. 1ISO 16128-1:2016 and ISO 16128-2:2017 — Guidelines on technical definitions and criteria for natural and organic cosmetic ingredients and products. ISO, Geneva.
  2. 2Sodium Ascorbyl Phosphate. PubChem CID 10990876. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov ↗
  3. 3SODIUM ASCORBYL PHOSPHATE. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  4. 4SODIUM ASCORBYL PHOSPHATE. CosIng u2014 European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=SODIUM%20ASCORBYL%20PHOSPHATE