Phenolic Compounds - Case 2: potato - Reaction with sulfite

20 important questions on Phenolic Compounds - Case 2: potato - Reaction with sulfite

What is the effect of vitamin C and sulfite?

They inhibit the browning reachton. Sulfite more efficient then vitamin C.

Why is sulfite more efficient then vitamin C in preventing browning?

Vitamin C lets your quinones react back to diphenols. So if all the vitamin C is used you will have brown coloring.

Sulfite inhibits the tyrosinase enzyme so the reaction can not occure anymore. Therefore you will need less.

Where does sulphite like to bind on the caffeic acid and why there?

You can have 2 resonant structures. The second is prefered. This gives a bit of a postive starch to the 2'position and therfore the sulphite binds there.
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What does sulphite do when it is bound to the caffeic acid?

The sulfo group prevents brown pigment formation. But does not inhibet the enzyme.

Why do the peaks lay more to the left in the socond graph?

You do reversesd phase chromatography.
The sulphite makes your compound more polair and therefore it will dilute faster.

Why could you have a loss of chloroginic acid?

  1. It could be that sulphite takes time to work and allready a part reacted with proteins
  2. At 320 NM the sulphite cloroginic acids have a different responce factor then the normal chloroginic acid molecules.
    This is incase what happend and you have a hapochromic and bathochromic shift.
    Calculations show that you have a quantative conversion.

What is the biggest error in canclualtion the molar extinction coefficient (E)?

The weighing needs to be super precise.

What is the effect on the chloroginic acid by adding sulphite?

All your chlorogenic acid will be intact and not bound to proteins.

Why does red wine not become green?

This is because the phenolics in wine also have acid groups which make them more resistant against turning green.

How can you loose the red color?

Because the conjugated system of the entocianins is interupted by the sulphite.

Which are the 2 main components that can also react with phenolic compounds

  • Cysteine
  • Glutathione

They bought have a sulfide group.

Which is the stronger nucleophile: thiol, cystein or sulfite?

A SH group is more reactive then a sulfite serounded by oxygen.
This is because the oxygen serounding the sulfide will draw some of the free electrons so therfore it is not as free as the electron pair in thiol and cystein.

cystein is stronger then glutathione because the Free electrons are presestn at the end of the molecule and not in the middle. The middle could mean that you have some steric hinder.

strongest: cystein, glutathione and sulfite.

With which machine can you determent where a sulpahte component will bind to in caffeic acid?

With H(proton)-NMR.

How can you see if there is couplin in H-NMR?

By looking if the peeks split up.

Hard to see for the small coupling and therfore you plot to an other measurements with slightly different settings against each other to get a 2D plot. In this you can clearly see if the signal is split up or not.

What ditermens if you have the sulfite group on the X, Z or Y position?

This is ditermont by the R group

What is the inductive and resonance effect?

Inductive: is electronegative elements that draws electrons to the negative atom and thereby create partial positive charges.

Resonance effect: double bonds are jumping around in the molecule.

Why is sulphite manly attached to the z-position? 

Because the resonant structures for x and y have to positive charges very close together. This is very unlikely to happen so this is not a resonant structure that is often formed. If this is unlikely then also not that many sulphite compounds can bind there.   

Why is sulphite mainly attached to the y –position in chlorocatechol?

·Four possible resonance structures
·Vicinal (partially) positive charges (+ and +) unfavourable
·Positive charge on xposition very unfavourable
·Position y and z seem equivalent, but y is the preferred site of addition (exp. evidence!)
·This might be explained by the stronger inductive electron withdrawing effect of chlorine compared to oxygen

Which position will the sulfite go to?

The X position, there are 2 resonant structures that result in a + loading on the x position.

Where will the sulfite bind on the epicatechin?

  • Position y is preferred, although charge distribution unfavourable
  • Steric hindrance apparently overrules charge distribution

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