Chemistry Education in New Zealand August 2010

Coffee chemicals
David Paterson
NZ Science, Technology and Mathematics Teacher Fellow with Syft Technologies Ltd., normally Head of
Science at Cashmere High School (email: pt@cashmere.school.nz)

Everyone loves coffee! And many spend large

amounts of time and money selecting the best coffee
house or lovingly preparing the perfect cup of coffee at home. But how many know exactly what they
are tasting, or realise that the molecules that contribute to the wonderful aroma of roasted coffee can be
highly toxic?
The chemicals that end up floating up from a cup of
coffee are the result of a whole host of reactions that
start with the coffee plant growing peacefully in a
tropical location and end with beans being subjected
to searing heat and scalding hot water. Variations in
any of the steps outlined below will cause changes in
the final flavour of the coffee:
Growing:
Temperature, rainfall, soil quality and the type of
coffee plant used.
Picking:
The timing and method of harvest.
Pulping and fermentation:
Coffee beans are separated from the fruit, or cherry,
by forcing the beans through a wire mesh then fermenting the beans to remove mucilage still attached.
Drying:
Beans are air- or sun-dried for up to four weeks to
reduce water content from 60% to 11%.

tral Nervous System stimulant. It has a very bitter

taste and when added to energy drinks it has to be
masked by flavour compounds to make the drink
palatable.

The flavour of coffee, however, comes from the over

1000 compounds that have been identified in coffee
vapour to date. These develop in the many stages of processing described above and come from a
wide variety of organic families. Some typical coffee compounds are shown in Table 1.
A new way of detecting and identifying volatile organic compounds is to use SIFT-MS (Selected Ion
Flow Tube Mass Spectrometry). This technique
has been recently commercialised by Syft Technologies Ltd. in Christchurch, a spin-off from research
at the University of Canterbury (see Paterson 2009,
2010). This year I have been using the Syft Voice
200 instrument to investigate the aroma compounds in instant and plunger coffees. Samples can
be prepared and measured extremely quickly using
the procedure illustrated in Fig. 1.

Storage:
Green coffee bean flavour peaks within one year.
Burlap bags are best as they allow for air flow around
the beans.
Roasting:
Hundreds of chemicals are produced when amino
acids react with sugars, and oxidations and caramelisation occur.

Push sample
needle into
headspace

Pour some coffee

into sample bottle

Grinding:
The size of particles produced determines which
method of brewing is best.
Brewing:
Using a French Press, drip machine or espresso.
For most people caffeine is the only compound they
consider associated with coffee, a typical cup containing between 65 and 175 mg caffeine. Caffeine
is produced by plants as a pesticide to paralyse and
kill certain insects, but is used by humans as a Cen-

Make a coffee
brew

Draw air from coffee headspace

through the Voice 200 for 1 minute

Fig. 1: Coffee Sampling Technique at Syft Technologies

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Chemistry Eduction in New Zealand August 2010

Table 1: A selection of compounds contributing to coffee aroma
Compound

Structure

Individual odour description

3-methylbutanal

Aldehydic, chocolate-like, peach, fatty

2,3-pentanedione

Buttery, caramel-like

Acetic acid

Acidic, sharp, pungent

Ethyl nononoate

Waxy, fruity, rose

Furfural

Nutty, roasted

Furfuryl methylsulfide

Leather-like

2,6-diethylpyrazine

Pyrazine, potato-like

Instant coffee
Naively I assumed that instant coffee contained
actual coffee bean material, but after doing some
simple research was surprised to find this is not the
case. Instant coffee is basically made by brewing up
an industrial sized coffee in a large stainless steel
tank from roasted beans, then separating the water
infused with coffee chemicals and either spray or
freeze drying it.
In order to see if the Syft technique could distinguish between different brands of coffee I analysed
the headspace of four different dry instant coffee
powders (labelled GCD, NG, EFD, CFD) simultaneously scanning for 36 different compounds. The
compound present at the highest levels, by far, was
acetic acid with an average concentration of 3000
ppb. The concentrations of a selection of other coffee volatiles are shown in Fig. 2.

Fig. 2: Volatiles in four instant coffee powders

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Clearly there are differences between the coffee

samples, but how significant are they? To answer
this question the data for all 36 compounds from all
four coffees was run through multivariate statistical analysis to look for similarities and differences
between samples. The SIMCA (Soft Independent
Modelling of Class Analogy) method looks for relationships between data sets and creates a visual representation of classes assigned in three dimensions.
The results are shown in Fig. 3 and indicate that
there are significant statistical differences between
the coffee types.

Fig. 3: SIMCA plot for four instant coffees

Chemistry Education in New Zealand August 2010

Plunger ground coffees

Four different commercially roasted and ground coffees were analysed in a similar way to the instant
coffees described above. The most striking difference was the vastly increased concentration of all
volatiles in the plunger coffees, note the scale on the
vertical axis in Fig. 4 compared to that in Fig. 2.

But what exactly is going on chemically? The Syft

technology provides a good way of following such
processes in real time. Some simple experiments
were carried out using the set-up shown in Fig. 5.

Air flows over

the coffee
bean and is
sampled by
the VOICE 200
instrument

Coffee bean in oven

Fig. 5:

Fig. 4: Volatiles in four plunger coffees

Firstly the oven was heated to 200oC, a single green

coffee bean placed in the centre, inside a stainless
steel tube with air being drawn through it. The instrument recorded the concentration of 35 different
volatile compounds for over 15 minutes. The resulting scan is shown in Fig. 6.

Furfural for example is present above the HE coffee sample at a concentration of approximately 4000
ppb or 4 ppm. This is above the Permissible Exposure Limit (PEL) for workers handling furfural as an
industrial solvent, which is 2 ppm for an eight hour
period.

Coffee bean roasting

All coffee aficionados know that coffee beans crack
twice during the roasting process which generally
follows this pattern:
Heating up: The green beans are slowly dried to become yellow and the beans begin to smell like toast
or popcorn.
The first crack occurs at approximately 205C, the
bean doubles in size, becomes a light brown colour,
and experiences a weight loss of approximately 5%.
As the temperature rises from 205C to approximately 220C, the colour changes from light brown
to medium brown and further weight loss occurs.
The second crack occurs between 225-230C, and
the roast colour is defined as medium-dark brown.
The second pop is much quicker sounding and the
beans take on an oily sheen.
Most people recommend stopping the process somewhere between the end of the first crack and midway through the second, depending on the flavour
required.

Fig. 6: SIFT-MS scan of coffee bean at 200oC

The major components of the two peaks are acetic

acid, methanol and propanoic acid. A second experiment was run again using a single coffee bean in the
same apparatus but this time placing the bean in the
oven at 195oC and heating to 250oC over 20 minutes.
The results of this experiment are shown in Fig. 7.
Acetic acid
Hexanoic acid

Methanol

Fig. 7: SIFT-MS scan of coffee bean at 250oC

Two distinct peaks can again be seen but with significantly increased number and concentration of volatiles produced at higher temperatures. The pattern of
compounds seems to match what is expected from

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Chemistry Eduction in New Zealand August 2010

the various Maillard and oxidation reactions, with

what is left in the beans providing the flavour in the
final cup of coffee.

Future possibilities
With a greater understanding of the chemical changes that occur during coffee processing the ability to
more precisely control the final flavour is possible.
Most coffee products result from combinations
of coffee beans from a variety of sources, blended
to give the desired flavour. By tracking the actual
chemicals released from particular beans more accurate blending should be possible.
A group of researchers at Nestl in Switzerland are
using a similar SIFT machine and a human sensory
panel to predict the final aroma profile of a particular coffee. Using sophisticated statistical analysis
the results from the sensory panel are matched to the
chemical signature from SIFT-MS analysis. Then
the machine is given a new coffee sample and is able
to produce an aroma profile, such as shown in Fig.
8, based on the relative concentrations of chemicals
detected. Thus the flavours of new blends can be
quickly established before the use of expensive panels of expert tasters.

ful coffee flavour. And see what sort of reaction you

get when you comment to your fellow coffee connoisseur that you particularly enjoy a touch of furfural in your brew, or a that a hint of pyrazine really
distinguishes an Ethiopian from a Blue Mountain.
Cheers!

References
1 Lopez-Galilea, I., Andriot, I., De Pena, M., Cid, C., &
Guichard, E. (2008). How does roasting process influence the retention of coffee aroma compounds by
lyophilized coffee extract? Journal of Food Science,
78(3), S165-171.
2 Akiyama, M., et al. (2008). Characterisation of headspace aroma compounds of freshly brewed arabica
coffees and studies on a characteristic aroma compound of Ethiopian coffee. Journal of Food Science,
73(5), C335-C446.
3. Perez-Martinez, M., et al. (2008). Application of multivariate analysis to the effects of additives on chemical and sensory quality of stored coffee brew. Journal
of Agricultural and Food Chemistry, 56, 11845-11853.
4. Rowe, D. (ed). (2005) Chemistry and technology of
flavors and fragrances. UK: Blackwell Publishing
Ltd.
5. Lindinger, C., et al. (2008). When machine tastes
coffee: instrumental approach to predict the sensory
profile of espresso coffee. Analytical Chemistry, 80,
1574-1581.
6. Coffee processing http://www.coffeeresearch.org (retrieved 20 Oct 2009)
7. Roasting profile http://www.ravensbrew.com/NewFiles/roastPage.html (retrieved 20 Oct 2009)
8. Coffee general information http://en.wikipedia.org/
wiki/Coffee (retrieved 20 Oct 2009)

Fig. 8: An aroma profile for a coffee brew

So next time you have a cup of coffee try to visualise

the incredible range of chemicals that are interacting
with your sensory receptors to produce that wonder-

ChemScrapes

9. Syft Technologies Ltd. http://www.syft.com/ (retrieved

20 Oct 2009)
10. Paterson, D. (2009). Furfural fuel and flavour molecule of the future? ChemEd NZ, No. 117, 2-4
11. Paterson, D. (2010). Vanilla: natural or not? ChemEd
NZ, No. 118, 2-6

Brendan Burkett

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