Database/Hair Conditioning/Vanillyl Butyl Ether
Route-dependent · ISO 16128

Is Vanillyl Butyl Ether natural?

It depends. The butyl part comes from petrochemical butanol; the vanillyl part is natural origin when the vanillin is made from wood lignin or other natural sources and petrochemical when it is made from guaiacol.

INCI nameVanillyl Butyl Ether
CAS82654-98-6
FormulaC12H18O3 · 210.27 Da
FunctionHair Conditioning · Fragrance
FeedstockVanillin is reduced to vanillyl alcohol and joined…

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
Synthetic vanillin + petrochemical butanolvanillin from petrochemical guaiacol; n-butanol from propylene0.00majority
Lignin or natural vanillin + petrochemical butanolvanillin from wood lignin, ferulic acid or eugenol; n-butanol from propylene0.65minorityvanillyl part 137.16 Da natural of 210.27 Da
Ask your supplier. A batch-specific certificate of origin or bio-based carbon test (ASTM D6866) settles which route applies.

How we scored it

Vanillyl part C8H9O2 137.16 Da + butoxy part C4H9O 73.12 Da (petrochemical butanol); water leaves in the etherification. Vanillin from wood lignin or other natural sources: 137.16/210.27 = 0.65; vanillin from petrochemical guaiacol: 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.

How it’s made

Acid-catalysed SN1 etherification (benzylic cation) of vanillyl alcohol with butanol. Each curved arrow moves one electron pair, and the film ends on the score above.

Where it comes from

Vanillin is reduced to vanillyl alcohol and joined to n-butanol (from petrochemical propylene) by acid-catalysed etherification. Most vanillin is made from petrochemical guaiacol; vanillin from wood lignin, ferulic acid or eugenol makes the vanillyl part natural origin.

Vanillyl butyl ether is made in two steps. Vanillin is first reduced to vanillyl alcohol (4-hydroxy-3-methoxybenzyl alcohol), usually with hydrogen over a metal catalyst.

The vanillyl alcohol is then heated with n-butanol and an acid catalyst. The acid protonates the benzylic OH so that it leaves as water, giving a benzylic cation that the ring's para-hydroxy group stabilises; the oxygen of butanol attacks that cation and loses its proton to form the ether. Water is the only by-product, and the ether is purified by washing and vacuum distillation.

In plain English

A warming agent: it gently triggers the skin's heat receptors, so it is used in lip plumpers, warming massage products and some hair-care products. It is made from vanillin and butanol, and its natural content depends on whether the vanillin comes from wood lignin or from petrochemicals.

Natural alternatives with the same function

Structure

2D structure of Vanillyl Butyl Ether

4-(butoxymethyl)-2-methoxyphenol

PubChem CID 5084146 ↗

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. 2Vanillyl Butyl Ether. PubChem CID 5084146. National Center for Biotechnology Information. pubchem.ncbi.nlm.nih.gov ↗
  3. 3VANILLYL BUTYL ETHER. CosIng — European Commission cosmetic ingredient database. ec.europa.eu/cosing ↗
  4. 4VANILLYL BUTYL ETHER. CosIng — European Commission database for information on cosmetic substances and ingredients. https://ec.europa.eu/growth/tools-databases/cosing/search?search=VANILLYL%20BUTYL%20ETHER