Database/Preservative/Dehydroacetic Acid
100% petroleum · ISO 16128

Is Dehydroacetic Acid natural?

No. Manufactured by self-condensation of diketene from petrochemical acetic acid/acetone feedstocks; no fermentation-acid route is used commercially.

INCI nameDehydroacetic Acid
CAS520-45-6
FormulaC8H8O4 · 168.15 Da
FunctionPreservative · Antimicrobial
FeedstockDehydroacetic acid is produced industrially by dimerizing diketene,…

How we scored it

Dimer of diketene (from ketene/acetic-acid pyrolysis); acetyl/acetone-type chemistry treated as petrochemical → 0 / 168.15 = 0.00.
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

Dehydroacetic acid is produced industrially by dimerizing diketene, itself made by pyrolyzing acetic acid (from petrochemical methanol carbonylation) to ketene. No natural-origin or fermentation route is used commercially for cosmetic-grade dehydroacetic acid or its sodium salt.

The industrial synthesis of dehydroacetic acid (DHA) typically begins with diketene. Diketene is a highly reactive intermediate that is dimerized under controlled conditions, often in the presence of a catalyst, to form dehydroacetic acid. This dimerization process involves the reaction of two molecules of diketene to form the cyclic structure of DHA.

The reaction is usually carried out in an inert solvent to manage the exothermicity and ensure selectivity. Common catalysts employed can include tertiary amines or other organic bases, which facilitate the cyclization and condensation reactions. The temperature is carefully controlled, typically within a moderate range, to optimize yield and minimize side product formation. Temperatures might range from ambient to slightly elevated, depending on the specific catalyst and solvent system used.

Following the reaction, the crude dehydroacetic acid is isolated from the reaction mixture. Purification is a critical step to achieve the high purity required for cosmetic applications. This often involves techniques such as recrystallization from suitable solvents (e.g., ethanol, water, or mixtures thereof) to remove unreacted starting materials, catalysts, and any byproducts. Filtration and drying are the final steps to obtain the solid, crystalline dehydroacetic acid product.

In plain English

Dehydroacetic acid is a synthetic ingredient commonly used in cosmetics and personal care products as a preservative. Its main job is to prevent the growth of bacteria, yeast, and mold, helping to keep your products safe and extending their shelf life. It's often found in lotions, creams, shampoos, and makeup.

This ingredient is manufactured through a chemical process starting from basic building blocks derived from petroleum. While it's effective and widely used, it's not considered a 'natural' ingredient according to the ISO 16128 standard because its production relies entirely on petrochemical sources and synthetic chemistry, rather than renewable plant or animal materials.

CosIng definition: Dehydroacetic Acid is the cyclic ketone that conforms to the formula:

Natural alternatives with the same function

Structure

2D structure of Dehydroacetic Acid

3-acetyl-6-methylpyran-2,4-dione

PubChem CID 122903 ↗

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. 2Dehydroacetic Acid. PubChem CID 122903. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov ↗
  3. 3DEHYDROACETIC ACID. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  4. 4DEHYDROACETIC ACID. CosIng u2014 European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=DEHYDROACETIC%20ACID