Bitterness in beer - Bitter acids

12 important questions on Bitterness in beer - Bitter acids

Where does the bitter taste in beer originate from?

The bitter acids accumulated in the glands of the hop flowers.

Which 2 types of bitter acids exist?

  • Alpha-acids (humulones)
  • Beta-acids (lupulones)

How do alpha and beta-acids look?

  • They contain a central 6-membered carbon ring
  • Prenyl chains
  • R-groups varying in length
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What is the difference between alpha- and beta-acids?

  • B-acids have an additional prenyl chain. It makes the molecule more hydrophobic, which influences the water-solubility of the beta-acids.
  • They are more apolar than the alpha-acids, and consequently have a lower water-solubility. Alpha-acids are reasonably water-soluble, but the beta-acids are not.

Are there a lot of beta-acids in hops?

No, only a minor part of the bitter acids are beta-acids. About 50x lower than of the alpha-acids. Due to their limited water-solubility, relatively small amounts are extracted during the brewing process.

Are alpha- and beta-acids bitter?

No, not that much. The iso-alpha-acids created after conversion of alpha-acids by the influence of heat are much more bitter.

What happens during heating in beer?

  • The Oktoberfest Umlagerung.
  • The 6-membered ring of the alpha-acids is converted to a 5-membered ring, via ring-contraction and rearrangement of the prenyl chain. Iso-alpha-acids are formed.

Why are bitter acids organic acids?

  • Normally organic acids contain a carboxyl group. The bitter acids lack this group
  • The acidic character of bitter acids (alpha, iso-alpha and beta) is induced by their keto-enol-tautomerism.
  • The hydrogen atom is easily released and can relocate over the molecule, making it the acidic hydrogen.

What is the pKa of iso-alpha-acids?

PH 5

When are trans- and cis-iso-alpha-acids formed?

During the ring contraction.

Which bitter acids have a lingering effect?

  • Iso-alpha-acids --> both cis and trans show lingering effect, as the fluorescence fades quickly
  • Alpha- and beta-acids --> stronger lingering effect. Hints at a stronger bitter response.

Which receptors respond to the bitter acids of beer?

T2R1 and T2R40

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