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Compound

4-Ethylphenol

The horse-and-sticking-plaster compound, made by Dekkera from a phenolic acid the fruit supplied, and the clearest case in cider of one molecule being a tradition in one glass and a fault in another.

Also called 4-EP, Ethylphenol.

Class
Phenolics
Formula
C8H10O
How often it matters
Central to how cider behaves

What it does in cider

How it is perceived

What the compound registers as, and at roughly what concentration. Perception is not a property of the molecule alone: sugar, tannin and carbonation all change where a threshold falls.

On threshold

Reported in wine at a few hundred micrograms per litre, and lower when combined with 4-ethylguaiacol, which almost always accompanies it. In cider the concentration at which it is judged a fault is not a fixed figure: several traditional styles carry it as an expected part of their character, and the same level that would condemn a fresh modern cider is unremarkable in a farmhouse one.

Descriptors it is responsible for

Sensory records that name 4-Ethylphenol as a cause. Each states the perception and the mechanism behind it.

The structure it moves

Structural dimensions this compound contributes to. Direction and amount depend on concentration and on what else is in the drink; the dimensions themselves are set out in full under Sensory.
DimensionWhat it is
Phenolic characterSmoky, spicy, leathery or medicinal aromas that sit apart from fruit.
Fermentation characterAromas made by the ferment rather than carried in from the fruit.
FreshnessWhether the drink smells and tastes of live fruit or of time and air.

What forms it

Processes that put this compound into the drink, or increase how much of it is there.

What removes or limits it

Processes that reduce it, hold it below a threshold, or stop it forming in the first place.

Faults it is implicated in

Being implicated is not the same as being a fault. Several of the compounds on this site are ordinary constituents of a sound cider and define a named fault only above a concentration.

Organisms that produce it

Which organism is responsible usually decides whether the compound is a feature or a symptom.

About 4-Ethylphenol

The chemistry is short and specific. Apple juice contains p-coumaric acid, mostly bound as p-coumaroylquinic acid. Free it, and an organism carrying a hydroxycinnamate decarboxylase converts it to 4-vinylphenol; an organism carrying a vinylphenol reductase as well converts that to 4-ethylphenol. Plenty of yeasts and bacteria have the first enzyme. Very few have both, and in cider the organism that matters is Dekkera bruxellensis, the same yeast that produces the equivalent character in wine and in certain Belgian beers.

Two features of the pathway explain how the character behaves in a cellar. The first is that the supply of substrate is usually the bottleneck. Free p-coumaric acid in fresh cider is scarce, and it is released slowly by hydrolysis over months, so phenolic character builds gradually through long maturation rather than appearing when the organism arrives. A cider bottled at six months and the same cider bottled at three years, both carrying Dekkera, will differ substantially. The second is that Dekkera is exceptionally patient. It tolerates alcohol, tolerates low nutrient levels, works slowly at cellar temperature and survives sulphite better than most spoilage yeasts, so it can persist in a barrel for years and transfer to every cider put into it.

Whether the result is a fault is not a chemical question. Traditional West Country farmhouse cider, much Norman cider, and a good deal of Asturian sidra carry recognisable ethylphenol character, and in those contexts it is part of what the style is — the farmyard and leather notes that experienced drinkers of those ciders expect and that competition style guidelines describe rather than penalise. In a clean, aromatic, fruit-driven modern cider the same compound at the same concentration is a spoilage marker, and one that indicates a hygiene problem likely to recur.

Control is entirely preventive, because nothing removes it once formed. The levers are the ordinary ones: adequate free sulphur dioxide at a pH where sulphur dioxide works, prompt racking off lees, filling vessels full, sterile filtration before packaging where the product demands it, and — decisively — attention to wood. Barrels are porous and are effectively impossible to sterilise by rinsing, so a producer who wants no ethylphenol and also wants oak has a genuinely difficult problem, and a producer who wants both character and control has to accept managing an organism rather than excluding it.

Related compounds

Compounds it is formed from, converted into, confused with, or routinely met alongside.

What people ask next

Questions readers ask about the things this page mentions. Each one goes to the section that answers it rather than to a page written to receive the question.

Where to go next

Sources

What this page rests on. Where a source is marked as registered rather than read, CiderHQ is recording that the body is authoritative on the subject without claiming to have worked through the document itself. See our evidence policy for what each state means.