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Section C:

EC (Evaluating and Concluding)

In red wine production the grape skins are left in the crushing. The skin contains compounds called anthocyanins (A+) which have complex molecular shapes as seen in the figure. Anthocyanins play a crucial role in developing the colour of red wine, however contribute little to the taste of wine. They have a positive charge on the molecule which enables it to absorb light and thus have colour. An anthocyanin has a carbohydrate (sugar, usually glucose) esterified at the 3 position. Naturally occurring pigments from grapes always have a sugar bonded at the 3 position, though other compounds such as hydroxycinnamates and acetate may be involved. The presence of this sugar helps the anthocyanin maintain solubility in water. If the sugar is hydrolyzed or lost, the solubility decreases and the molecule will be destabilized and lost. Factors that affect the expression of colour in a wine by anthocyanins include: by pH, SO2, temperature, polymerisation and copigmentation. Here the main effects analysed are pH (internal and external), SO2 and temperature. Anthocyanins react with water (hydration reaction) as follows:

A+(aq) + 2 H2O(l) AOH(aq) + H3O+(aq)


The A+(aq) cation form is red and the AOH(aq) form is colourless. Thus LeChateliers principle can be used to understand the effect on the colour of the wine as the pH changes.

Sulfur dioxide is added to the process to kill any bacteria and wild yeast. In this step of wine manufacturing SO2(g) enters an equilibrium and the bottle is closed.

SO2(g) SO2(aq) SO2(aq) + 2 H2O(l) H3O+(aq) + HSO3-(aq)


The HSO3-(aq) also reacts with hydrated anthocyanins to form another colourless compound according to the following reaction.

H3O+(aq) + AOH(aq) + HSO3-(aq) ASO3H(aq) + 2 H2O(l)


The ASO3H(aq) form is also colourless

Investigate the Equilibrium reactions stated here. Research further to evaluate what happens to these equilibria during fermentation, maturing by aging and exposure to the atmosphere after opening. What is the pH range of general red wines and the complex nature of the equilibrium between anthocyanins and acidity?

Solubility Rules

Anion
Nitrates (NO3-), Acetates (CH3COO-) Chlorides (Cl-)

Soluble
All common cations

Insoluble*
No common cations

Most common cations

AgCl, HgCl2. PbCl2 is borderline. AgBr, HgBr2, PbBr2. AgI, HgI2, PbI2. SrSO4, BaSO4, SnSO4, PbSO4, Ag2SO4. CaSO4 is borderline. Most common cations

Bromides (Br-) Iodides (I-) Sulfates (SO42-)

Most common cations Most common cations Most common cations

Hydroxides (OH-)

NaOH, KOH, LiOH, NH4OH, Sr(OH)2, Ba(OH)2. Ca(OH)2 is borderline. Na2S, K2S, Li2S, (NH4)2S, MgS, CaS, BaS, SrS Na2CO3, K2CO3, Li2CO3, (NH4)2CO3 Na3PO4, K3PO4, Li3PO4, (NH4)3PO4 Na2SO3, K2SO3, Li2SO3

Sulfides (S2-)

Most common cations

Carbonates (CO32-)

Most common cations

Phosphates (PO43-)

Most common cations

Sulfites (SO32-)

Most common cations