Chemistry for Everyone

edited by

Products of Chemistry

George B. Kauffman
California State University
Fresno, CA 93740

Our Everyday Cup of Coffee: The Chemistry behind Its Magic

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Marino Petracco
Research and Technical Development Department, illycaff S.p.A., via Flavia, 110-34147 Trieste, Italy; [email protected]

Coffee beverages are so popular all over the world that

there is hardly the need to describe them. Their fragrance
and flavor are the first stimuli that strike our senses early in
the morning, they crown an excellent meal, and are recurring
visions during never-ending work sessions. After all, our cup
of coffee is a dear old friend, about which we only think we
know everything. When examining it from a chemists viewpoint, we must nevertheless acknowledge that its nature is
so complex that vast gaps remain in scientific understanding.
The history of coffee starts with the legends about the
discovery of coffee as a food. These legends tell the story of
Abyssinian shepherds consuming the seeds of some Coffea
plant, by chewing either raw or cooked, generally roasted,
fruits (1). For those of you who have tried to munch on a
bean, it is hard to imagine that the success of coffeetoday
the most traded food commoditycould have ever occurred,
had those primitive habits persisted.
On one hand, it seems logical that the appeal of coffee
to those early food-science pioneers derived essentially from
their experiencing stimulation that proved to be beneficial
to their activities (2). In other words, the primordial reason
for coffee consumption must have been the physiological effects of caffeine in the human organism, by now well documented (3). On the other hand, it is pretty obvious why coffee
has become so popular, achieving the position of the second
most largely consumed beverage after water. It is a question
of flavor or, better still, of overall impact on our senses. Sensory evaluation, which used to be considered magic because
taste is a matter of taste, is now earning the status of a highly
respected analytical tool (cup-testing is its technical name),
able to produce key information with good reliability.
While people like the flavor of coffee, they do not like
the disturbing sensory feeling of chewing and swallowing hard
particles deriving from a bean. This fact makes beverage preparation a fundamental step for enjoying the benefits of this
commodity and sometimes for transforming it into a specialty.
Production and Consumption Patterns
The coffee tree belongs to the Rubiaceae family, where
two species of the genus Coffea are economically important,
C. arabica and C. canephora (4). The latter is better known
as robusta coffee, a term derived from its ability to thrive in
the harsh environment of the west African rain forest. Arabica
coffee, which is indigenous to the Ethiopian highlands and
prospers in cooler mountain regions of the tropical belt (up
to 2500 m), accounts for more than two-thirds of the world
production and is considered to give the best, mildest cup of
coffee.

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Figure 1. Laborers handpicking a harvest of coffee fruit.

Ripe cherries, the name for the fruit of the coffee plant,
are usually picked by hand (Figure 1). The immediate postharvest process, either direct sun drying or depulping, releases
two seeds per fruit, the raw coffee beans. Beans are usually
shipped in jute bags to the roasting facilities overseas.
As an international trade commodity, global coffee production ranks second in value only to petroleum and results
in more than 6 billion kg of coffee per year. Cultivation occurs
in some 50 tropical countries (Figure 2). As most of these
coffee-producing countries have less-developed economies,
coffee often represents the main source of hard-currency
income.
Coffee consumption has spread worldwide, especially in
Europe, the United States, and Japan (Figure 3). The type of
related beverages and the pattern of consumption are strictly
associated with social habits and culture of the country. Differences in the raw bean composition, in roasting conditions,
and in the extraction procedures used to prepare coffee brews
result in a great diversity of chemical composition in the final
product, the cup of coffee. Also the size of a single serving is
highly variable, ranging from 15 mL of concentrated Italian
espresso to over 250 mL in many English-speaking countries.
Moreover, a coffee serving can be derived from brewing a

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Brazil

Nordic countries

Vietnam

German countries

Colombia

France & Italy

Indonesia

USA & Canada

Spain & Greece

Mexico
Robusta

India

Arabica

Japan
Australia

Cte d'Ivoire
Ethiopia

United Kingdom

Guatemala

Russian Federation
China

Uganda
0

200

400

600

800

1000

1200

1400

1600

1800

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10

Consumption per Capita / (kg yr1)

Production / (106 kg yr1)

Figure 2. Major coffee-producing countries in year 2001 (5).

Figure 3. Major coffee-consuming countries in year 2000 (5).

quantity of roasted ground coffee ranging from as little as 5 g

to as much as 15 g or more.
A remarkable difference between coffee and all the other
beverages is the extraordinary variety of brewing techniques
that have been developed and are used traditionally in different countries; decoction methods (boiled coffee, Turkish
coffee, percolator coffee, and vacuum coffee), infusion methods (drip filter coffee and Napoletana), and the original Italian pressure methods (Moka and espresso) (6).
Espresso is a way to enjoy a cup of coffee that is gaining
a great deal of popularity throughout the world, especially
in the European countries with Latin origins and in recent
years also in the United States and Japan. Its roots are found
in the Italian culture of foods and beverages, which developed a typical lifestyle linked to coffee drinking (7). Its success lies in the greater satisfaction it gives to the consumer,
when compared with coffee brews prepared by other methods.

Raw Coffee Composition and Changes from Roasting

O
H3C

CH3
N

Proximate analysis of raw arabica coffee indicates: 12%

moisture, more than 50% carbohydrates, 16% lipids, and 10%
proteinaceous material. With reference to compounds that are
more coffee-specific, yet abundant, one should mention the
1.2% of caffeine (Figure 4), also known as trimethyl-xanthine,
and the 6.5% of chlorogenic acid1 (Figure 5), the esterification product of the polyphenol caffeic acid with quinic acid.
The main compositional differences of robusta coffee as
compared to arabica coffee are higher caffeine content (2.2%),
lower lipid content (10%), and higher chlorogenic acid content (10%). The presence of some of the less-expensive
robusta coffee in a blend with arabica coffee can be determined precisely, by analyzing for presence of the diterpene
16-methoxycafestol, which is specific to the canephora species (8). The typical compositions of raw coffee for the two
main botanical species are shown in Table 1.
Raw coffee can hardly be defined as edible, and there
are no claims of such material to produce a beverage, even if
the active physiological component, caffeine, can be effectively extracted by hot water from crunched raw seeds. The
grassy, astringent taste of such a brew is surely a deterrent
against any commercial venture in that direction. The roasting

N
CH3

Table 1. Typical Composition of Raw Coffee

for the Two Main Botanical Species

Figure 4. Structure of caffeine.

C. arabica
(Arabica) (%)

Components
Caffeine
Minerals

HO

Lipids

OH
O

OH

HO
O
O

OH
OH

Figure 5. Structure of chlorogenic acid.

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0.91.2

1.62.4

3.04.2

4.04.5

12.018.0

Trigonelline

C. canephora
(Robusta) (%)

9.013.0

1.01.2

0.60.75

11.013.0

11.013.0

Aliphatic Acids

1.52.0

1.52.0

Chlorogenic Acids

5.58.0

7.010.0

Oligosaccharides

6.88.0

5.07.0

50.055.0

37.047.0

Proteins

Polysaccharides

NOTE: The data are expressed as percentage of dry matter (9).

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Chemistry for Everyone

process is required to produce a coffee that, when ground to

increase surface area exposed to water, allows people to enjoy a pleasurable beverage.
During roasting, pyrolytic reactions take place inside
coffee cells (Figure 6) that could be compared to minuscule
autoclaves with an internal pressure up to 25 bar. This is due
to the unusual thickness of the cell walls as compared to other
plants seeds. The highest final roasting temperature, as applied to beans to be used for the preparation of espresso coffee, may reach 220 C (10).
Roasting modifies chemical composition drastically: while
the overall contents of caffeine and lipids remain almost unchanged, the quantities of sugars and of free or protein-bound
amino acids decrease substantially. These are consumed as reactants in Maillard reactions (11). These reactions of condensation between a carbonyl group of a reducing sugar and an amino
group are fundamental to the chemistry of cooking: their labile
intermediates decompose into a number of low molecular weight
compounds, the most reactive of which polymerize to ill-known
structures. In coffee they produce, along with the release of large
volumes of carbon dioxide, many hundreds of volatile substances
imparting roast coffees characteristic aroma (12).
Since the structures of the polymeric Maillard products,
called melanoidins, are largely unknown, they must be generically defined as macromolecular materials (mass > 10,000 Da)
that are brown and contain nitrogen. Melanoidins usually act
as pigments, imparting the color of roasted coffee; because they
are water soluble, they are one of the major components of
coffee beverages (13). Their composition varies in different
foods: for coffee, it has been reported that melanoidins contain approximately 30% carbohydrates, 9% proteins, and 33
42% of polyphenols (14). This suggests the possibility of the
presence of a non-colored carbohydrate skeleton bearing a variety of chromophoric substructures, coming in part from the
Maillard reaction and in part from degradation of chlorogenic
acids. The latter is also the source of further coffee aroma compounds, pertaining to the classes of catechols and guaiacols.
While initial research on roasted coffee was largely devoted to understanding factors that could improve flavor, in
the last decade melanoidins, too, have attracted much interest because of their influence on flavor binding (15) and on
foam stabilization (16).

Coffee Is More Than Caffeine

Little is known with certainty about the physiological aspects of coffee, but a bewildering array of health and mood
effects are attributed to it. For the reasons mentioned above,
any figure quoted in quantitative assessments of effects of coffee consumption must be taken with caution. A plethora of
epidemiological studies on the effect of coffee have been published in the last 20 years (17) although their conclusions have
not always led to clear-cut answers. More than 90% of the
research carried out on the physiological properties of coffee
has been devoted to caffeine, an alkaloid that stimulates the
central nervous system (18, 19). Caffeine, regarded as the most
used pharmacologically active substance, is also present in
other common beverages such as tea, colas, and chocolate.
While producing a general habit, its daily consumption by
the majority of human population has never been substantiated as addictive; this is probably because caffeine, unlike opioids, nicotine, and even alcohol does not act on the limbic
system of our brain, where reward sensation originates (20).
For coffee lovers who wish to reduce the stimulant effects of caffeine intake without abating the number of cups
per day, industry has developed a number of processes that
virtually eliminate the alkaloid directly from the green beans
(21). However, decaffeination technology is quite complex
and beyond the scope of this article. It resorts to procedures
based on extraction with various dissolving agents, followed
by thorough removal of the solvent and recovery of the caffeine, which mainly ends up in pharmaceuticals as well as in
other artificial beverage formulations. Unfortunately, some
of the aroma precursors are extracted as well as caffeine.
In any case, coffee is much more than caffeine. Its complex composition and the presence of other substances as yet
unidentified, but with evident physiological effects, indicate
that further research is needed to demonstrate both the wholesomeness of coffee as well as the favorable effects this beverage can have on humans. For example, one of the constituents
found in green coffee beans that may be beneficial to human
health is trigonelline (Figure 7), which has received considerable attention as its thermal transformation products are
important both from sensory and nutritional points of view.
Found in quantities up to 1%, trigonelline is readily degraded
by roasting into several aroma compounds (mainly pyrazines)
and into nicotinic acid, or niacin, that is also known as vitamin PP (pellagra preventing) or vitamin B3 (22). An average
coffee consumers niacin intake can represent up to 50% of
the recommended daily dose. Traces of another vitamin precursor, the lipophilic tocopherol or provitamin E, have been
identified in the oil fraction of coffee.

COO

COOH
+

N
N
CH3
trigonelline

Figure 6. Fluorescence microscopy of roasted coffee cellular structure.

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nicotinic acid

Figure 7. Thermal degradation of trigonelline results in nicotinic

acid and other products (not shown).

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Chemistry for Everyone

Other constituents of coffee beans are phenolic compounds, among which chlorogenic, caffeic, p-coumaric, and
ferulic acids were identified. Most of those substances display
potent antioxidant activity in vitro and are supposed to play
an important protective role in several human pathologies acting as antiinflammatory, antimutagenic, and anticarcinogenic
agents. Their absorption, metabolic fate, and availability for
antioxidant protection in humans are not, however, fully understood.
Recently, research has given evidence that coffee possesses
an antioxidant activity attributable to the development of
Maillard reaction products. Antioxidant activity increases up
to the medium-dark roasted stage then decreases with further roasting. This experimental observation is explained by
a partial decomposition of the freshly formed antioxidant
compounds (23). A particularly interesting finding is the fact
that antioxidant activity is also present in human blood serum, as an acute result of the administration of 200 mL of
coffee beverage prepared starting from 12 g of roast and
ground coffee blend (24). Latest research points to an ionic
Maillard product, methylpyridinium, as an active antioxidant
and detoxifying agent (25).
Chromatography of Volatiles
When considering that coffee is the second most largely
consumed beverage after water, one must acknowledge that
its popularity has been achieved for its flavor. It is therefore
no surprise that considerable money is spent on coffee aroma
research, mainly by the major companies.
Aroma is the ensemble of volatile molecules given off
by roasted coffee that can be perceived by the human sense
of olfaction either as odor or as flavor. To make the difference clear, it is useful to explain that olfaction operates
through thousands of receptors located in the inner mucosae of the nose. The receptors can be reached directly when
inhaling the molecules arising from ground coffee or from
the cup; odor is appraised this way. The perception of flavor
comes when volatile substances evolve in the mouth after sipping and reach the nasal cavity by the pharyngeal (backward)
pathway (6).
Green coffee beans, straight from the tree via traditional
agricultural practices, do not show either roasted beans color
or aroma. Both are formed during the roasting process, where
the latter develops mainly as a consequence of Maillard reacTable 2. Main Aroma Compounds Identified
in Roasted Coffee
Compound

Dilution Factor

3-Mercapto-3-methylbutylformate

2048

2-Ethyl-3,5-dimethylpyrazine

2048

(E)--Damascenone

2048

4-Vinylguaiacol

0512

2-Isobutyl-3-methoxypyrazine

0512

2,3-Diethyl-5-methylpyrazine

0512

3-Hydroxy-4,5-dimethyl-2[5H]-furanone

0512

5-Ethyl-3-hydroxy-4-methyl-2[5H]-furanone

0512

NOTE: Data from ref 29.

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tions and concentrates mostly in the coffee oil, an effective

aroma carrier. Albeit made up of almost one thousand volatile
compounds, aroma constitutes just 0.1% of the weight of
roasted ground coffee (26).
The identification of some early aroma compounds, such
as guaiacols and furfurylmercaptans, was done by food chemistry pioneers in the 1930s (27). From then on, the number
of compounds identified has grown greatly as a result of gas
chromatography techniques. Because a key coffee aroma compound was never identified, it appeared to make little sense to
increase the number of compounds by lowering detection
thresholds. A newer concept, GC-olfactometry, made the
search of sensory-active compounds possible, spotting them
via sniffing ports at the end of a chromatographic column (28).
Today, the aroma analysis of a coffee sample includes
several steps:
Isolation of volatile substances by steam distillation, followed by extraction with solvents such as diethylether or
pentane. The relevant standard method is the simultaneous
distillation extraction, also known as the LikensNickerson
technique. An alternative, solvent-free technique based on
adsorption has begun to gain popularity, and furthermore,
it requires a small sample size. It is called solid phase microextraction.
Fractionation by a variety of chromatographic configurations
with packed or capillary columns operated under an oven
and injection temperature program. Flame ionization detectors are still used for peak sensing. Pulsed flame photometric
detectors are indispensable when looking for sulfur-containing compounds. For sensory correlation, gas chromatographs must be equipped with sniffing ports where trained
or naive assessors can record their qualitative and quantitative impressions.
Identification of peak compounds, facilitated by the universal use of affordable analyzers based on mass spectrometry (MS). For deeper investigation and better recognition
of more complex compounds, multiple fragmentation instruments are also at hand, the so-called MSMS system,
in the triple quadrupole configuration or even in the MSn
configuration made possible by use of an ion trap.
Final confirmation of structure would require NMR analysis or IR analysis, if the sample quantity could allow it. For
this purpose, some attention is currently being paid to the
exploitation of preparative GC.

Several hundred substances, such as hydrocarbons, aldehydes, and esters, along with sulfurated and nitrogenated
compounds, have been identified as a result of these techniques. Some of them have been highlighted as key aroma
compounds, applying the concept of flavor dilution factor.
This refers to the process of consecutive halving of the quantity of concentrate injected into the column, to find the greatest dilution for which aroma is still perceivable from the
sniffing port at the relevant elution time (Table 2).
Along with the search for volatile compounds contributing to coffee aroma, the same degree (or even more) of attention has been paid to spotting the agents responsible for
off-flavors, namely the obnoxious sensations caused by rotten
or defective beans. Unfortunately, those bad guys can be
easily noticed by our sense of olfaction even when present in

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very small quantities. Among them, there are some infamous

coffee taints, such as the old crop note, the stinker defect, the jute bag flavor, and the peasy flavor: each of those
flaws is responsible for substantial reduction in value of the
affected lots.
The most remarkable achievement in this field is the discovery of the compounds responsible for two frequent negative traits: the so-called Rio-taste and the flavor typical of
robusta. Both have been ascribed to metabolic pathways of
infecting microorganisms producing tiny quantities, in the subppb (parts per billion) range, of potent odorants identified as
2,4,6-trichloroanisole and 2-methylisoborneol, respectively
(Figure 8). The former compound is possibly the most potent
odorant discovered so far: its sensory detection concentration
threshold has been reported (30) to be as low as 0.03 ngkg,
corresponding to a few thousandths of parts per trillion!
Cup-Testing as an Analytical Tool
In the coffee industry, some objective form of sensory
evaluation is needed to ascertain overall product quality along
with the constancy of that quality over time and in varying
process conditions (31). The tool commonly put to use is
a panel of assessors, who may be either coffee experts (professional cup-testers) or naive consumers after a very basic
training. The reason for employing more than one person is
obvious since, by averaging responses, the risk of incorrect
judgment owing to a possible bad mood or minor illness of
one person is minimized. Another panel potential is the synergy that can be gained by debating coffee characteristics
among the assessors during open sessions. This procedure may
yield more information, since individual sensitivities and perception thresholds may be different.
Sensory tests may be grouped in three basic types, listed
by increasing difficulty for the panel members:
Trio tests, used to determine whether any perceivable difference exists between two samples. In this configuration
each sample is split in two cups, but one cup is discarded
and only three cups are presented to the panel. The assessors are requested to tell which is the foreign single cup,
as opposed to the pair of sister cups. A variation called
duotrio presents the panel with five cups, where two sister foreigners are shuffled with three sister controls. This
approach has the advantage of making hits by chance much
less likely (110 vs 13).
Duo tests, where two or more single cups are presented to
the panel and panel members are asked to rank the cups of
coffee in relationship to one sensory variable. When more
than one variable is to be determined, a pre-filled card proves
useful to summarize the evaluations.
Absolute tests, in which some complex variable, such as
aroma or overall merit, is to be determined by comparison
with a mental paradigm present in each assessors memory
by previous experience. Coffee aroma profiling (32) as well
can be included in this type, since it is based on assessors
recall of variegated flavor knowledge present in their experience.

Cup-testing sessions cannot be too long or frequent during the day, because some fatigue develops after the first dozen
cups. This is particularly true for espresso tasting, owing to
the presence of tiny coffee oil droplets in emulsion; they stick
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O
Cl

CH3

H 3C

CH 3

Cl
HO

CH3
CH3

Cl

2,4,6-trichloroanisole

2-methylisoborneol

Figure 8. Structures of compounds responsible for off-flavor odor

in coffee.

on the tongue and mouth membranes and impart a lingering aftertaste. Rinsing the mouth with water, albeit necessary between each sampling, is not effective in removing the
taste completely. On the contrary, cool whole milk seems to
be better for this purpose perhaps because, being itself an
oil-in-water emulsion, it can displace coffee oil droplets from
the tongue by dilution.
A collection of sensory data can be utilized for the calibration of instrumental screening methodologies such as near
infrared reflectance (NIR). This analysis, using spectroscopy
in the near-infrared wavelengths (11002500 nm), is a technique that measures scanned monochromatic light absorption
by the material to be examined, whose energy is dissipated in
rotational and vibrational movements of the molecular bonds
and ultimately transformed into heat (33). The energy absorption pattern provides information about the molecular
configuration of the tested material.
NIR analysis takes advantage of the fact that it is a rapid,
nondestructive fingerprinting technique apt to supply simultaneous forecasts of many chemical characteristics of the
sample examined, provided that a good calibration has been
previously obtained by statistical correlation with conventional, time-consuming analytical methods. This secondary
method is suitable also for modeling sensory data, bearing
in mind that since several preprocessing steps are needed to
obtain the actual coffee beverage tested, regression coefficients
not better than 60% are to be expected (34).
Five Senses Are Involved in Espresso Enjoyment
Few everyday experiences can compete with a good cup
of coffee, based on sheer sensory pleasure. It is clear that most
of the quality of such a beverage is determined by its flavor
or, better still, by its overall sensory impact. In this context,
espresso is the brewing method that offers the consumer the
most powerful experience, even if a high quality cup it is not
easy to obtain. Espressos very strength, the ability to concentrate aromas, is also its weak point because, while enhancing
qualities, at the same time it brings out all the latent defects
that may exist in the raw material.
The main features of espresso coffee derive from the way
it is prepared:
Preparation on order. Unlike other brews that wait for a
customer, it is the latter who must wait for his or her espresso
cup.
Brewing by a specific methodpercolationthat uses high
water pressure (around 9 bar).
Rapid extraction (30 s), admitting into the cup just the best,
most palatable material.

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Coffee connoisseurs consider perfectly brewed espresso to

be the superlative form of coffee, because its special preparation amplifies and exhibits the inherent characteristics of the
beans. To the young food chemist, espresso could be a challenge for deeper research, because its structure of a polyphasic
colloidal system along with its complex composition may be
seen as the quintessence of all the other techniques by which
coffee can be brewed (36). Knowing espresso is to know coffee in all its forms.

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Figure 9. Cross-sectional detail of a typical espresso percolation

device.

Percolation is a process in which a small quantity of hot

water under pressure is squeezed through a tightly packed
layer of ground roasted coffee, the so-called cake (Figure 9).
This process efficiently produces a concentrated brew containing not only soluble solids, but also some lipophilic substances lacking in other brew types.
The resulting beverage is peculiar from a physical and
chemical perspective, inasmuch as the foam on the top and
the opaque brew are unique to espresso. The former, a velvety, thick, reddish-brown froth called crema, is composed
of tiny gas bubbles arranged in a honeycomb structure that
locks in the coffees distinctive aroma. The latter is due to
the presence of a dispersed phase formed by small oil droplets in emulsion that are perceived in the mouth as a special
creamy sensation, the body. Furthermore, oil droplets preserve many aromatic components that would otherwise either escape into the atmosphere or be destroyed by contact
with water as in the other brewing techniques. Because of
oil droplets the rich coffee taste lingers in the mouth for several minutes (35).
Often considered a strong cup of coffee, espresso fully
deserves this attribute based on its sensory properties. When
it comes to caffeine, on the contrary, espresso is surprisingly
moderate with an average content of less than 80 mg (if prepared from pure arabica). This is due both to the small size
of the serving, usually brewed from as little as 6.5 g of roasted
ground coffee, and to the short contact time with water allowed during extraction. Since caffeine dissolution is slow, a
good quarter of the caffeine remains with the spent grounds.
As already stressed, espressos main characteristics are of
sensory nature. All human senses (with the moot exception
of hearing: think about the distinctive whistling of coffee
makers!) are involved in appreciation of a cup of espresso:
Vision evaluates foams aspect, examining its color and consistency and persistence.
Touch assesses the beverage mouthfeel, or body, a property linked with density and viscosity.
Taste judges the bitteracidic balance and the presence of a
sweet caramel-like aftertaste.
Olfaction evaluates both the fragrance of the vapors arising
from the cup (the direct pathway) and the flavor of the volatile substances evolving in the mouth, by upstream diffusion.

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Conclusion
To develop a fruitful knowledge base, worthy of being
called coffee science, research strategy should prompt scientists with different backgrounds (food technology, food
chemistry and biochemistry, nutrition, consumer science) to
team up and work closely with coffee companies in investigating all aspects that are crucial to product acceptance. Superior coffee is the result of close control over a multitude of
factors in the field, in industrial processing, and in the cup.
Science, with chemistry in a prominent place, is a key ally to
strengthen the quality chain from agriculture to industry,
keeping in mind that each and every link of the chain deserves the best possible care to prevent any decline in the overall result. Only in this way can the highest satisfaction be
assured to every customer enjoying a cup of coffee. Scientificallysure!but without forgetting the magic behind it.
Note
1. The classical Greek meaning of chlorogenic is turning
something green. Actually, a better name for chlorogenic acid
would be caffeoylquinic acid.

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