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Compound

Epicatechin

The flavan-3-ol that apple procyanidins are almost entirely built from, and the most bitter of the phenolic monomers a cider contains.

Also called (−)-epicatechin.

Class
Phenolics
Formula
C15H14O6
How often it matters
Regularly encountered

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

Among apple phenolic monomers it is the clearest bitter contributor; free monomers in general are more bitter and less astringent than the polymers assembled from them.

Descriptors it is responsible for

Sensory records that name Epicatechin 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
BitternessA taste sensed at the back of the tongue, distinct from the drying grip of astringency.
TanninThe phenolic material that gives cider structure, grip and ageing capacity.

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.

Chain length splits bitterness from astringencyAt a fixed 750 milligrams per litre in model cider, astringency rises with procyanidin chain length while bitterness peaks in the middle and falls away.Astringency — rises with chain lengthBitterness — peaks at the tetramerMonomerDimerTetramerLong polymerAverage degree of polymerisation →Held constant: 750 mg/LConcentration, ethanol, fructose andmalic acid identical at every point.
At a fixed 750 milligrams per litre in model cider, astringency rises with procyanidin chain length while bitterness peaks in the middle and falls away.
Described in full
Shape
A horizontal axis of increasing average degree of polymerisation, marked with four positions: monomer and dimer at the left, tetramer in the middle, and long polymer at the right. Two labelled bands run across it — an astringency band that thickens steadily from left to right, and a bitterness band that is thin at the left, thickest at the tetramer, and thin again at the right.
Astringency
Increases with the degree of polymerisation. Longer chains carry more sites to cross-link salivary proteins, and it is the loss of lubrication in the mouth that reads as drying rather than as taste.
Bitterness
Peaks at the medium chain length. In the study behind this figure, the tetramer fraction was the most bitter of the four tested; both the shorter and the longer fractions were less so. Bitterness is a receptor event, and a molecule can be too large to fit the receptor while remaining perfectly able to bind a protein.
The fixed condition
Every point on this axis is 750 milligrams of procyanidin per litre in the same model solution of water, ethanol, fructose and malic acid. Concentration is held constant so that the axis shows chain length alone. The companion study found the chain-length effect is not identical at every concentration, so this figure describes one concentration.
The side effect
A note beneath the axis records that in the same experiments the perception of sweetness and sourness also moved with procyanidin concentration, although the fructose and the malic acid were identical in every sample. Tannin does not only add its own sensations; it changes the reading of the others.
What this is not
A model solution is not cider. It contains no pectin, no protein, no carbonation and none of the hundreds of compounds a fermentation makes, and every one of those can shift how a phenolic behaves on the palate.

About Epicatechin

Apple tannin is epicatechin tannin. Where grape procyanidins involve a mixture of flavan-3-ol units and where some fruits build largely on catechin, apple procyanidin chains are made from (−)-epicatechin almost throughout, with (+)-catechin appearing mainly as the terminal unit at the end of a chain. Analysing the ratio between the two is one of the standard routes to estimating how long the chains in a juice are, since every chain has one terminal unit however long it is.

Free epicatechin — molecules that never got built into a chain — is present in juice as well, and it is the most straightforwardly bitter of the apple phenolics. A juice rich in monomers and short oligomers reads bitter; the same total phenolic content held mostly as long polymers reads astringent instead.

Its catechol ring makes it a ready substrate for polyphenol oxidase, and once oxidised it does not simply turn brown and stop. Epicatechin quinones couple with other phenolics, including other procyanidins, building larger structures that eventually leave the solution. This is the chemistry behind the observation that oxidised juice makes a cider both paler in phenolic bite and more stable to further air.

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.