C H A P T E R
14
Volatile Chemicals from Thermal Degradation
of Less Volatile Coffee Components
Takayuki Shibamoto
Department of Environmental Toxicology, University of California, Davis, CA, USA
List of Abbreviations
UV Ultraviolet
GC  Gas chromatography
MS  Mass spectrometry
MRPs  Maillard reaction products
14.1 INTRODUCTION
The history of coffee goes back to the ninth century.
A unique nature of coffee was noticed when a goat
became friskier after eating red berries of a local shrub;
subsequently, a goat herder who saw this phenomenon
tasted some of the berries and experienced a pleasant
feeling. In the beginning of the twelfth century, the first
roasted and boiled coffee was prepared and consumed
by Arabians. Later, a beverage coffee became to be
known by people in Europe, and the first coffee house
was opened in England in the mid-seventeenth cen-
tury. Since then, coffee has been gradually introduced
to the world and has become the most popular bever-
age today.
Many people prefer coffee because of its character-
istic pleasant flavor given by the chemical’s so-called
aroma volatiles. Analysis of coffee volatiles began in the
mid-1950s using conventional techniques such as paper
chromatography, ultraviolet (UV), and infrared. Later,
the invention of gas chromatography (GC) advanced
the analysis of volatile chemicals significantly. In partic-
ular, the development of GC/mass spectrometry (MS)
in the late 1960s progressed identification of volatile
chemicals in foods and beverages remarkably.1 Even
before the invention of GC/MS, nearly 350 volatile
chemicals in coffee were identified.2 After the advance-
ment of GC/MS, the number of volatile chemicals iden-
tified in coffee steadily increased, and now has reached
Coffee in Health and Disease Prevention
http://dx.doi.org/10.1016/B978-0-12-409517-5.00014-0 © 2015 Elsevier Inc. All rights reserved.
more than 800.3 This number is proposed to increase
following the development of analytical techniques in
the future.
Coffee volatile chemicals vary from very low molecu-
lar weight compounds, such as methane4 and formalde-
hyde,5 to relatively less volatile compounds quinoxaline,
such as 2,3-dimethylqunoxaline.6 Among volatile chemi-
cals identified in coffee, relatively low molecular weight
heterocyclic compounds, including furans, pyrroles,
thiophenes, thiazoles, oxazoles, pyridines, and pyr-
azines, contribute to the characteristic roasted coffee
flavor. For example, 2-furylthiol possesses a strong
coffee-like aroma.7 More than 400 heterocyclic volatile
compounds have been reported in roasted brewed coffee
today.3 These chemicals produce extremely complicated
coffee aromas.1
There are numerous reports on the formation of aroma
chemicals in roasted coffee. Generally, they are formed
from the following:
1. D  egradation of lipids.
2. Degradation of carbohydrates and sugars.
3. Maillard reaction between nitrogen-containing
compounds and carbonyl compounds.
4. Degradation of proteins and amino acids.
5. Degradation of less volatile constituents,
including chlorogenic acids, quinic acid, and
caffeic acid.
  
All these reactions occur upon heat treatment.
Therefore, the roasting process is an ideal condition
for formation of volatile compounds from green cof-
fee beans because they contain various chemical raw
materials of volatiles. When coffee beans are roasted,
the compositions of the chemical raw materials,
including carbohydrates, proteins, and amino acids,
change significantly. The reduction of these chemicals
129
130 14.  DEGRADATION PRODUCTS IN COFFEE
in green coffee beans upon roasting indicates that
the Maillard reaction occurs during roasting to form
various aroma chemicals. At first, polysaccharides or
lipids degrade into low molecular weight carbonyl
compounds and then react with ammonia, which
formed from proteins or amino acids, to form hetero-
cyclic aroma compounds.8
14.2  VOLATILE CHEMICALS FORMED
FROM LIPIDS IN COFFEE
It is well known that many carbonyl compounds, such
as acetaldehyde, malonaldehyde, glyoxal, and diacetyl,
are formed from lipids upon oxidation.9 Figure 14.1
shows typical volatile lipid peroxidation products and
their generally recognized proposed formation path-
ways, established in the early 1980s.10,11 Some carbonyl
compounds are known to possess characteristic aromas.
For example, acetaldehyde possesses reminiscent of cof-
fee in high dilution and has been used to create vari-
ous imitation flavors including coffee.7 The presence of
acetaldehyde in coffee was reported in the mid-1920s.12
Since then, there have been many reports on analysis
of acetaldehyde in coffee.3 Moreover, aldehydes and
ketones shown in Figure 14.1 are important carbonyl
reactants to form heterocyclic flavor chemicals reacting
with amines.13
Formation of α-dicarbonyl compounds such as gly-
oxal, methyl glyoxal, diacetyl—one of the major car-
bonyl compounds formed by lipid peroxidation—in
oxidized edible oils have already been demonstrated in
the mid-1980s.14 Later, those α-dicarbonyl compounds
were reported in coffee.15 Moreover, these α-dicarbonyl
compounds are known to produce volatile heterocyclic
flavor chemicals reacting with amines via the Maillard
reaction as mentioned above.
Also in the mid-1980s, 5-alkyl (C0–C8) furanones—
possessing a caramel-like odor with low aroma thresh-
old values16—were reported in a heated beef fat.17
Later, 2-methyl-3(2H)-furanone was found in coffee,18
and then eight furanones were reported in coffee up to
now.3 Furan is formed via reactive aldehydes, such as
2-alkenal, that are lipid degradation products.19 Furans
are the most abundant volatile chemicals found in cof-
fee, and more than 130 furans have been reported in
coffee.3
There is another possible pathway in which a lipid
produces various low molecular weight radicals, such
as %CH3, %C]O, %C]O(CH3), and these radicals sub-
sequently combine to yield various volatile chemicals.
This pathway could be proposed when the reaction
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I.   INTRODUCTORY AND GENERAL TEXT

 14.3  Volatile Chemicals FormED from Carbohydrates and Sugars in Coffee
systems absorb high levels of energy from high tem-
perature, such as cooking, or photoirradiation.20 In
fact, when lipid, squalene was irradiated with UV
light, volatile reactive carbonyl compounds were
formed.21,22,23
14.3  VOLATILE CHEMICALS FORMED
FROM CARBOHYDRATES AND SUGARS
IN COFFEE
It has been also known since the 1960s that sugars
degrade into many low molecular weight carbonyl
compounds.24,25 Figure 14.2 shows typical volatile
sugar degradation products and their generally rec-
ognized proposed formation pathways. Figure 14.3
shows that furans and related compounds are also
found as sugar degradation products. In this path-
way, a polysaccharide is hydrolyzed to monosugars
that produce various monosugar isomers, includ-
ing fructose and glucose via keto-enol tautomeriza-
tion. Subsequently, the key intermediates, diketones
for carbonyl compounds formation, are produced by
a dehydration reaction. Once diketones are formed,
further oxidative degradation occurs to form vari-
ous reactive carbonyl compounds, such as diacetyl.26
131
The carbonyl compounds are formed by cleavage at
a keto-enol bonding in a diketone to form various
less molecular weight carbonyl compounds.20 Conse-
quently, these carbonyl compounds react with amines
to form Maillard reaction products (MRPs). Therefore,
these carbonyl compounds participate in the forma-
tion of characteristic coffee flavors as reactants.
One Canadian research group has been investigating
intensively the formation pathways of low molecular
weight volatile compounds from oxidative degra-
dation of sugars and amino acids using 13C-labeled
compounds since the late 1990s. One of their studies
proposed that the major formation pathway of furan
from hexose involves an intermediate 1-deoxyosoe.19
Also, they proposed that low molecular weight reac-
tive carbonyl compounds, such as acetaldehyde,
react to each other to produce different chemicals.27
In addition, acetol, pyruvaldehyde, and glyceral-
dehyde were proposed to form from glucose via an
intermediate 1-deoxyglucosone or 3-deoxyglucosone
yielded from a glucose/l-methionine or l-alanine
Amadori product.28,29 These reports suggest that
amino acids play an important role in oxidative deg-
radation of sugars or lipids and may act as a catalyst
for formation of reactive carbonyl compounds from
lipids and sugars.

FIGURE 14.2  Proposed formation pathways of volatile sugar degradation products.

I.   INTRODUCTORY AND GENERAL TEXT

132 14.  DEGRADATION PRODUCTS IN COFFEE

FIGURE 14.3  Furans and related

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14.4  VOLATILE CHEMICALS FORMED
IN COFFEE BY MAILLARD REACTION
A French chemist, L.C. Maillard, advanced the
theory that the reaction of a carbonyl group of a
sugar and an amine group of an amino acid produces
browning pigments and polymers in 1912. Since then,
many studies using so-called Maillard model systems
consisting of a sugar and an amino acid have been
conducted to investigate the formation of various
chemicals in foods and beverages, including flavors,
mutagens, carcinogens, antidiabetics, and antioxi-
dants.30 It is obvious that the Maillard reaction occurs
in coffee beans during roasting because composi-
tions of carbohydrates and amino acids/proteins are
reduced significantly by roasting.31
Since the first comprehensive review on Maillard reac-
tion was published in 1953,32 there have been numerous
articles, books, and book chapters on the formation of
volatile chemicals via Maillard reactions.33,34,35,36,37 Most
flavor chemicals formed by the Maillard reaction are
not first degradation products from less volatile chemi-
cals, such as lipids and carbohydrates, but secondary
products formed from those less volatile degradation
products via Maillard reaction. Therefore, a detailed dis-
cussion on Maillard reaction products formed in coffee
is not the main subject of this chapter, but rather a brief
discussion of the role in Maillard reaction in formation
of flavor chemicals in coffee is presented. Any mixtures
containing an amine group (amino acids, proteins, etc.)
and a carbonyl group (sugars, carbohydrates, etc.) pro-
duce a large number of so-called MRPs. Currently, more
than 1200 MRPs are reported.33,34,35,36,37 Among these
I.   INTRODUCTORY AND GENERAL TEXT
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products, heterocyclic compounds are known to contrib-
ute characteristic flavors to roasted coffee significantly.7
14.5  VOLATILE COMPOUNDS FORMED
FROM AMINO ACIDS AND PROTEINS
It is generally proposed that nitrogen atoms in het-
erocyclic compounds come from NH3, formed from an
amino acid via Strecker degradation.38 Many volatile
chemicals were identified in Maillard systems consist-
ing of a sugar and NH3,39,40 suggesting that amine com-
pounds play as a souse of ammonia in the Maillard
reaction system. Some compounds with no nitrogen
atom, such as carbonyl compounds and furans, form in
Maillard reaction systems, also suggesting that an amine
compound acts as a catalyst for sugar or lipid degrada-
tion as mentioned above. For example, maltose degraded
into diacetyl through an Amadori product intermediate
when it was incubated with l-lysine.34 Various degrada-
tion products, in particular α-dicarbonyl compounds, of
oligosaccharides were reported in the glycine-catalyzed
Maillard reaction system.41 In contrast, 13C-isotope study
demonstrated that an alkyl group from an amino acid
was incorporated into a side chain of pyrazines found in
an alanine/glucose model system.42
When an aqueous solution of l-cysteine alone was
irradiated with UV light at 253.7 nm for 24 h, some vola-
tile heterocyclic compounds, including thiophene, pyr-
azine, thiazole, thiazoline, and pyrrole, were formed,43
suggesting that various low molecular weight radicals
form from a sugar and an amino acid, and then subse-
quently these radicals are combined to form heterocyclic
 14.6  Volatile Chemicals Formed from Quinic Acid, Caffeic Acid, and Chlorogenic Acids 133
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FIGURE 14.4  Proposed formation pathway of volatile chemicals from chlorogenic acids.

compounds as mentioned above. It is obvious that there
are two possible pathways—thermal oxidative reac-
tion28 and radical reaction20—involved in Maillard reac-
tion systems.
14.6  VOLATILE CHEMICALS FORMED
FROM QUINIC ACID, CAFFEIC ACID,
AND CHLOROGENIC ACIDS
Quinic acid, caffeic acid, and chlorogenic acids are
present in green coffee beans. Among individual chemi-
cals found in green coffee beans, chlorogenic acids are
one of the most unique chemicals present in coffee
beans. The chlorogenic acids content varies in different
green coffee beans. One study on a total content of chlo-
rogenic acids in green coffee beans was 61 mg/g in Nica-
raguan, 64 mg/g in Sumatran, 69 mg/g in Ethiopian,
and 86 mg/g in Panamanian.44 The composition of chlo-
rogenic acids in green beans reduces from 6.5% to 2.5%
by roasting,31 suggesting that they degrade into volatile
chemicals by heat treatment. When Ethiopian green cof-
fee beans (total content of chlorogenic acids, 69 mg/g)
were roasted under different conditions—Light (230 °C,
12 min), Medium (240 °C, 14 min), City (250 °C, 17 min),
and French (250 °C, 21 min), the total content of chloro-
genic acids in roasted beans was reduced to 32 mg/g by
Light roast, 20 mg/g by Medium roast, 1.8 mg/g by City
roast, and 0.34 mg/g by French roast.44
It is obvious that the total amount of chlorogenic
acids is reduced parallel to the intensity of heating
conditions; the more intensive condition the more deg-
radation. Surprisingly, there is no report on the forma-
tion of volatile chemicals from chlorogenic acids except
the report by Moon et al. (2009).45 One study reported
the isomerization products of chlorogenic acids but
not their degradation products in roasted coffee.46
Figure 14.4 shows a proposed formation pathway of
volatile chemicals from chlorogenic acids, prepared
based on the proposal advanced previously.45 Among
52 volatile chemicals identified in thermal degradation
of a chlorogenic acid, 15 major chemicals identified
were shown in Figure 14.4.45 In this proposed pathway,
a chlorogenic acid is hydrolyzed into quinic acid and
caffeic acid that subsequently degrade into various
volatile chemicals. Furans and cyclohexanones were
formed mainly from a quinic acid moiety via dehy-
dration. Aromatic compounds are also formed from a

I.   INTRODUCTORY AND GENERAL TEXT

134 14.  DEGRADATION PRODUCTS IN COFFEE
quinic acid moiety, but they form mainly from caffeic
acid moiety because a benzene ring exists already in
caffeic acid moiety. Many different and complex reac-
tions are involved in the formation of these volatile
chemicals from chlorogenic acids. Reactions involved
are dehydration, decarboxylation, dehydration, defor-
mic acid, keto-enol tautomerization, and homolytic
bond cleavage as well as free radicals.45
Catechol formed the greatest amount (58,960.8 μg/g),
followed by 4-ethylcatechol (31,437.5  μg/g), phenol
(6637.8 μg/g), benzoic acid (2445.8 μg/g), 2,5-dimethylfu-
ran (2231.0 μg/g), 2-methylcyclohexanone (411.6 μg/g),
1,2-cyclohexadione (260.5  μg/g), furfuryl alcohol
(259.9 μg/g), pyridine (251.9 μg/g), 2-cyclohexen-1-one
(107.4 μg/g), 3-ethylcatechol (103.4 μg/g), 2-hydroxycin-
namic acid (74.8 μg/g), cyclotene (70.6 μg/g), 1-hydroxy-
2-propanone μg/g),
(35.5  and 2-methylpyrazine
(22.6 μg/g) from a chlorogenic acid degradation under
various roasting conditions.45 The presence of chemicals
that are obviously not directly formed from a chloro-
genic acid, such as 1-hydroxy-2-propanone and 2-meth-
ylpyrazine, indicates the involvement of low molecular
weight radicals formed by the heat treatment as men-
tioned above.
14.7  SUMMARY POINTS
• T remendous numbers of volatile chemicals are
formed in coffee by roasting.
• Major components of green coffee beans,
carbohydrates, proteins, and lipids degrade into
low molecular weight volatile compounds via heat
treatment.
• Lipids and carbohydrates produce carbonyl
compounds that react with amines to form
heterocyclic flavor chemicals.
• Maillard reaction plays an important role in
characteristic coffee flavors.
• Chlorogenic acids, one of the major components
of green coffee beans, produce many furans and
aromatic compounds by roasting.
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