Database/Tonic/Ethyl Menthane Carboxamide
Route-dependent · ISO 16128

Is Ethyl Menthane Carboxamide natural?

It depends. The menthane ring comes from menthol (mint oil or pine myrcene = natural; thymol- or citral-derived = petrochemical); the carboxamide carbon, nitrogen and ethylamine part are petrochemical.

INCI nameEthyl Menthane Carboxamide
CAS39711-79-0
FormulaC13H25NO · 211.34 Da
FunctionTonic
FeedstockMenthol is converted to menthyl chloride, carboxylated through…

Why the score varies

This ingredient is made commercially by more than one route, and ISO 16128 scores the feedstock actually used. Without a supplier certificate of origin the value cannot be claimed.

RouteFeedstockNOIShareNotes
Menthol from cornmint oil or pine myrceneMentha arvensis oil or pine turpentine (myrcene)0.66approx. 60% (estimate)
Menthol from thymol (m-cresol) or citral (isobutylene)petrochemical0.00approx. 40% (estimate)
Ask your supplier. A batch-specific certificate of origin or bio-based carbon test (ASTM D6866) settles which route applies.

How we scored it

Skeleton C10H19 139.3 from menthol (route-dependent); carboxamide C=O 28.0 (CO2 carbon), NH 15.0 and ethyl 29.1 treated as petrochemical. Natural-menthol route 139.3 / 211.3 = 0.66; thymol/citral menthol route 0.0.
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

Menthol is converted to menthyl chloride, carboxylated through a Grignard step to p-menthane-3-carboxylic acid, then amidated with ethylamine. Which menthol source dominates is uncertain; mint-oil and pine-myrcene menthol is assumed to be somewhat larger than thymol- or citral-based synthetic menthol.

In plain English

A menthol-derived cooling compound (known as WS-3) used to give a cooling feel in skin, lip and oral products. It is made from menthol by adding an ethyl-amide group using petrochemical reagents.

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Structure

2D structure of Ethyl Menthane Carboxamide

N-ethyl-5-methyl-2-propan-2-ylcyclohexane-1-carboxamide

PubChem CID 62907 ↗

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. 2Ethyl Menthane Carboxamide. PubChem CID 62907. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov ↗
  3. 3ETHYL MENTHANE CARBOXAMIDE. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  4. 4ETHYL MENTHANE CARBOXAMIDE. CosIng u2014 European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=ETHYL%20MENTHANE%20CARBOXAMIDE