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Volatile phenols: smoke, spice and sticking plaster

One compound family behind three very different things — oak toast character, Brettanomyces spoilage, and smoke taint.

The short answer

Volatile phenols are a family of compounds that reach wine by three quite different routes: extracted from toasted oak, produced by Brettanomyces yeast from grape-derived precursors, or absorbed from wildfire smoke. The chemistry overlaps, which is why the descriptors do too.

Overview

Grouping these together is unusual, and it earns its place: understanding that the smoky note in an oaked wine, the medicinal note of a Brett-affected one and the ashtray note of a smoke-tainted one belong to the same chemical family explains a great deal of otherwise confusing tasting vocabulary.

How it works

The mechanism, at the scope it has actually been established.

Oak toasting thermally degrades lignin in the wood, producing guaiacol and related compounds associated with smoke, spice and toast. These are extracted into wine during barrel contact and are a normal, intended part of oaked wine.

Brettanomyces converts hydroxycinnamic acids naturally present in grapes into 4-ethylphenol and 4-ethylguaiacol, associated with sticking plaster, farmyard and clove characters. Published thresholds for these vary widely with the wine matrix.

Wildfire smoke contains the same guaiacol and cresol family. Grapes absorb them through the skin, and the vine binds much of the load into glycosides — sugar-bound forms that are not volatile and therefore not detectable by smelling the fruit.

Those bound forms are the central difficulty with smoke taint. They can be released during fermentation and, more slowly, in bottle, so a wine can taste clean at pressing and show ashy character months later.

The three routes are distinguishable analytically, which matters commercially, but the sensory overlap is real.

Compounds named on this page

Where a compound comes from is chemistry; what it smells like is perception. These are kept apart deliberately.

Guaiacol
A volatile phenol from lignin breakdown — in toasted oak and in wildfire smoke alike. Associated with smoke, toast, ash, medicinal. Caution: The same compound family is a desirable oak character and the core of smoke taint. Origin, quantity and intention distinguish them, not chemistry.
4-ethylphenol
The principal Brettanomyces marker, associated with sticking-plaster and farmyard character. Associated with sticking plaster, farmyard, horse, smoky. The AWRI gives roughly 368 µg/L in a neutral Australian red, rising as high as 425 to 569 µg/L in wines with strong green character or considerable oak. There is therefore no single threshold. Caution: A minority of drinkers value at low concentrations exactly what others reject. WineHQ reports the thresholds and does not adjudicate the preference.

Sources

Sources consulted

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