Maillard Reaction, Strecker Degredation and Caramelisation

June 20th, 2006

In the next of my apparent series of articles on all things coffee and chemistry I am going to tackle in a pleasant (I hope) depth these three types of reactions as they appear all the time in coffee articles. Obviously we are going to need to get into a bit of chemistry but hopefully it will remain understandable!

All of these are forms of non-enzymatic browning – opposed to reactions causing foods to go brown because of one of many enzyme actions, such as your apple turning brown when bitten into and left for a bit. This seems an obvious distinction, but I think it is important to include.

As usual – questions or mistakes in the comments!

The Maillard Reaction

Luis-Camille Maillard was the chemist after whom these particular reactions are named, as he was one of the first to investigate them in 1912. The term describes a very specific set a reactions – browning reactions occuring between amino acids and reducing sugars.
Amino acids are the building blocks of proteins, and just as the 26 letters of the alphabet can be used to write an infinite number of different texts, the 20 standard amino acids are put together to create a potentially infinite number of different proteins.
I won’t dwell on the chemistry but all amino acids have the same end to the chain:

The R symbolises the rest of the chain, and obviously this is the bit that is different from amino acid to amino acid.
So anything with protein in it is a candidate for the maillard reaction. All we need now is the presence of a reducing sugar.

The term reducing sugar implies something more interesting than what we find. Simply put a reducing sugar is any sugar with an aldehyde group. We often talk about aldehydes in coffee’s complex aroma chemistry (such as benzaldehyde – which has the characteristic smell of bitter almonds, and is used in just about any almond syrup), but to be an aldehyde means you have to have this arm tacked onto the molecule somewhere:

(again R is the the Rest of the molecule)
A list of reducing sugars is full of familiar names: fructose, glucose, lactose and maltose to name a few.
However, and this is important, sucrose – table sugar – is not a reducing sugar and takes no part in the Maillard Reactions (but does get involved in caramelisation).

These two react together and form new molecules with a brown colour – melanoidins (which you may recall being quite important to crema). Heat is not absolutely necessary, you could mix the two, put them in the fridge and they would turn brown – just very slowly! Heat helps speed the whole thing up. Equally they can happen with water present, but water slows it down. Without the sugar there can be no browning – this is why quakers stand out in roasted coffee, and are so pale.

Problems arise in the full description of reactions because different sugars and different amino acids produce different molecules, and then to complicate the picture these molecules begin to react and interact further. It is almost a cascading set of reactions. Therefore there are a great deal of different compounds created, both aromatic and non-volatile.

There is of course commonality between Maillard Reactions in different food products – coffee and chocolate share a great deal in terms of flavour as many of the same reactions have occured. Roast beef should also share some similar chemistry to roasted coffee, though whether there is enough commonality to make the combination palatable is debatable (though I have a collection of recipes for roasted and barbequed meat with a coffee crust!)
The Maillard reactions are the reason that milk left on a steam wand quickly turns brown.

These reactions are dependent on a few variables: the different amino acids available, the pH, the amount of water, any salts and the period of time held at a temperature.

The Strecker Degradation

This is one I thought I should include because I see it referenced quite a lot, in any text concerning roasting chemistry and is instrumental in the creation of the brown pigment as well as a myriad of volatile aromatics. It falls under the umbrella of, and requires compounds created by, the Maillard Reactions. Unfortunately this one isn’t so simple to explain.

It involves amino acids again, but instead of reacting with a sugar it is reacting with a molecule with two carbonyl groups, which look like this:

The compounds begin to trade parts of themselves, one of the carbonyl groups ending up on the amino acid (the acid having lost on carbon from its chain) creating an aldehyde as wll as an amino ketone. This is an intermediary stage and reactions continue to create many different volatiles.

I have refrained from making explicit descriptions of groups of aromatics. Ketones could be broadly described as having buttery, caramel flavours but key aromas in both raspberries and grapefruit are ketones.
Therefore I don’t think it is terribly helpful for me to claim that furans taste of this, and aldehydes taste of that….
Perhaps a description of each group of aromatics – esters, phenolics, terpenoids and thiols – would make an interesting article.

Caramelisation

Much slower than Maillard reactions, and requiring much higher temperatures these reactions begin exclusively with sugars. They really begin up around 150C to 180C, with water being lost from the sugar molecule beginning the chain of events. In all cases the sugar is converted to a furfuryl. These are a type of furans that have a caramelly, slightly burnt and also slightly meaty notes. The same compound is produced via a different route in the Mailllard reactions. However it is with prolonged high temperature that many other types of aromas are generated.
Caramelisation is more predictable than Maillard reaction due to less variation in the starting compounds. Without the sulphur or nitrogen found in the amino acids caramelisation is unable to produce flavours as meaty as Maillard reactions

It is interesting to note how the sugar solutions taste changes in caramelisation. A sugar solution initially will be sweet with no aroma. Through caramelisation it becomes both sour and a little bitter, as a rich aroma develops. Generally the longer sugar is caramelised the less sweet it tastes.

Extended Reading:
General Book: The Maillard Reaction
Website: Course Information and A nice Diagram
Coffee Specific: The Science of Quality

Hopefully this will give the reader an insight into the basics of the different types of chemistry going on when you apply heat to food and it turns brown. Because of the broad range of applications I haven’t focused this one completely on coffee, though no doubt that will change when I come to review it. Any mistakes or obvious omissions then please let me know!

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