Database/Skin Conditioning Agent/Retinyl Palmitate
Mostly petroleum · ISO 16128

Is Retinyl Palmitate natural?

Mostly not. Synthetic retinol (285 Da, petrochemical beta-ionone route) is esterified with palm palmitic acid (239 Da), giving 239/525 = 0.46.

INCI nameRetinyl Palmitate
CAS79-81-2
FormulaC36H60O2 · 524.9 Da
FunctionSkin Conditioning Agent · Antioxidant
FeedstockSynthetic retinol from acetone-derived beta-ionone (BASF or DSM)…

How we scored it

Giving 239/525 = 0.46.
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.

How it’s made

O-Acylation of retinol by palmitoyl chloride (Et₃N). Each curved arrow moves one electron pair, and the film ends on the score above.

Where it comes from

Synthetic retinol from acetone-derived beta-ionone (BASF or DSM) esterified with palm-derived palmitic acid.

The industrial synthesis of Retinyl Palmitate primarily involves the esterification of retinol with palmitic acid. Retinol itself is typically synthesized via a complex multi-step process. A common route begins with the cyclization of isoprene units, followed by various functional group transformations. For example, citral can be synthesized from petrochemical sources and then converted to retinol through a series of reactions including Grignard additions and oxidations. Alternatively, retinol can be synthesized from beta-ionone, which is also derived from petrochemical feedstocks.

Palmitic acid, a saturated fatty acid, can be obtained from natural sources like palm oil or coconut oil through hydrolysis and subsequent purification. However, for cosmetic-grade Retinyl Palmitate, it is often synthesized or purified from sources that are integrated with petrochemical supply chains to ensure consistency and purity. The esterification reaction between retinol and palmitic acid is typically carried out under mild conditions, often in the presence of an acid catalyst (like sulfuric acid or p-toluenesulfonic acid) or a dehydrating agent, at moderate temperatures (e.g., 50-100°C) to drive the reaction to completion and remove water as a byproduct.

Purification of the resulting Retinyl Palmitate is crucial. This usually involves steps such as washing to remove residual acids and catalysts, followed by crystallization from suitable solvents (like ethanol or hexane) to obtain a high-purity product. Techniques like chromatography may also be employed for further refinement. The final product is typically a pale yellow, viscous liquid or crystalline solid, sensitive to light, air, and heat, necessitating careful handling and storage.

In plain English

Retinyl Palmitate is a form of Vitamin A, often called a "pro-vitamin" because your body can convert it into retinol, which is the active form of Vitamin A that benefits the skin. It's commonly found in skincare products like anti-aging creams and serums. Vitamin A is known for its ability to help promote skin cell turnover, which can lead to smoother, more radiant skin, and it also plays a role in supporting collagen production, helping to reduce the appearance of fine lines and wrinkles.

In terms of its origin, Retinyl Palmitate is typically made through a chemical process. While one of its components, palmitic acid, can be derived from plant oils, the other key component, retinol, is usually synthesized from petroleum-based chemicals. This means that the overall ingredient is considered to be derived from non-renewable, petroleum sources. It's valued for its stability and gentler action compared to other forms of Vitamin A, making it a popular choice for many cosmetic formulations.

CosIng definition: Retinyl Palmitate is the ester of Retinol and palmitic acid.

Natural alternatives with the same function

Structure

2D structure of Retinyl Palmitate

[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] hexadecanoate

PubChem CID 5280531 ↗

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. 2Retinyl Palmitate. PubChem CID 5280531. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov ↗
  3. 3RETINYL PALMITATE. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  4. 4RETINYL PALMITATE. CosIng u2014 European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=RETINYL%20PALMITATE