Coffee Chemistry
- Aroma
The aroma of a coffee is responsible for all
flavor attributes other than the mouthfeel and sweet, salt,
bitter, and sour taste attributes that are perceived by
the tongue. Therefore, it might be said that the aroma is
the most important attribute to specialty coffee. Even instant
coffee has the components responsible for stimulation of
our taste buds. The difference, however, is that instant
coffee lacks most of the aromatic volatile compounds, which
causes a dramatic alteration in the overall flavor.
Aroma is perceived by means of two different mechanisms.
It can either be sensed nasally via smelling the coffee
grounds or brew through the nose or more importantly retronasally.
Retronasal perception occurs when the coffee is either present
in the mouth or has been swallowed and aromatic volatile
compounds drift upward into the nasal passage.
The number of aromatic compounds found in coffee increases
every year. Today, the number is well over 800 and as our
analytical methods become more precise more will be uncovered.
Yet, the perception of aroma is dependent upon both the
concentration of the compound and its odor threshold. With
that said, understanding coffee aroma is not as difficult
as understanding how over 800 compounds interact with the
olfactory epithelium. It is probable that a relatively small
group of compounds that share both a high concentration
and a low odor threshold make up the fragrance we know as
coffee aroma. This article will discuss the recent research
that has narrowed in on these aroma impact compounds.
Illy listed the following the development of volatile compounds
in coffee (112):
1) Maillard or non-enzymatic browning reaction between nitrogen
containing substances, amino acids, proteins, as well as
trigonelline, serotonine, and carbohydrates, hydroxy-acids
and phenols on the other.
2) Strecker degradation.
3) Degradation of individual amino acids, particularly,
sulfur amino acids, hydroxy amino acids, and proline.
4) Degradation of trigonelline.
5) Degradation of sugar.
6) Degradation of phenolic acids, particularly the quinic
acid moiety.
7) Minor lipid degradation.
8) Interaction between intermediate decomposition products.
In a review article published by Clarke, he asserts that
various research groups have identified 150 aliphatic compounds
including 56 carbonyl compounds and 9 sulfur containing
compounds; 20 alicyclic compounds, including 10 ketones;
60 aromatic benzenoid compounds, including 16 phenols; 300
heterocyclic compounds, including 74 furans, 10 hydrofurans,
37 pyrroles, 9 pyridines, 2 quinolines, 70 pyrazines, 10
quinoxalines, 3 indoles, 23 thiophens, 3 thiophenones, 28
thiazoles, and 28 oxazoles (34).
Table 1 shows the compounds that are likely to be the
most influential in coffee aroma This data was
compiled from the work of both Grosch and Blank and is by no
means exhaustive. It should be noted that the
OAV alone does not dictate which compounds are the most
important compounds present in coffee, but rather suggests
compounds that are likely to have a large impact on the
aroma of coffee. The furans are found to be the most predominant
group of compounds amongst the coffee aromatics. They typically
have caramel-like odors since they result from the pyrolysis
of sugars. Shibamoto claims that furans produce key aroma
notes when secondary reactions take place with sulfur containing
compounds (77).
| Table 1. Important compounds in coffee aroma
as summarized by Grosch. Click on compound name for
more information. |
| Volatile1 |
Conc.
(mg/L)1 |
OAV1 |
Aroma
Description2 |
|
(E)-ß-Damascenone
|
1.95x10-1
|
2.60x105
|
honey-like,
fruity |
|
2-Furfurylthiol
|
1.08
|
1.10x105
|
roasty
(coffee) |
|
3-Mercapto-
3-methylbutylformate
|
1.30x10-1
|
3.70x104
|
catty,
roasty |
|
3-Methyl-2-buten-1-thiol
|
8.20x10-3
|
2.70x104
|
amine-like |
|
2-Isobutyl-3-methoxypyrazine
|
8.30x10-2
|
1.70x104
|
earthy |
|
5-Ethyl-4-hydroxy-
2-methyl-3(2H)-furanone
|
1.73x101
|
1.50x104
|
|
|
Guaiacol
|
4.20
|
1.10x104
|
phenolic,
spicy |
|
2,3-Butanedione
(diacetyl)
|
5.08x101
|
3.40x103
|
buttery |
|
4-Vinylguaiacol
|
6.48x101
|
3.20x103
|
spicy |
|
2,3-Pentanedione
|
3.96x101
|
1.30x103
|
buttery |
|
Methional
|
2.40x10-1
|
1.20x103
|
potato-like,
sweet |
|
2-Isopropyl-3-methoxypyrazine
|
3.30x10-3
|
8.30x102
|
earthy,
roasty |
|
Vanillin
|
4.80
|
1.90x102
|
vanilla |
|
4-Hydroxy-2,5-dimethyl-
3(2H)-furanone (Furaneol)
|
1.09x102
|
1.70x103
|
caramel-like |
|
2-Ethyl-3,5-dimethylpyrazine
|
3.30x10-1
|
1.70x102
|
earthy,
roasty |
|
2,3-Diethyl-5-methylpyrazine
|
9.50x10-2
|
1.00x102
|
earthy,
roasty |
|
3-Hydroxy-4,5-dimethyl-
2(5H)-furanone (Sotolon)
|
1.47
|
7.50x101
|
seasoning-like |
|
4-Ethylguaiacol
|
1.63
|
3.00x101
|
spicy |
|
5-Ethyl-3-hydroxy-4-methyl-
2(5H)-furanone (Abhexon)
|
1.60x10-1
|
2.00x101
|
seasoning-like |
|
Table
References
1)
Grosch, 151.
2) Blank et al., 124.
|
The pyrazines are the second most abundant
class of compounds and contribute to the roasted, walnut,
cereal, cracker, or toast-like flavors in coffee. Along
with thiazoles, the pyrazines have the lowest odor threshold
and therefore significantly contribute to the coffee aroma.
Next, the pyrroles are responsible for some of the sweet,
caramel-like, and mushroom-like aromas in coffee. Conversely,
the thiophens are known to have a meaty aroma and are
thought to be produced from Maillard reactions between
sulfur containing amino acids and sugars. Thiazoles have
an even smaller presence in the overall aroma and are
said to be formed via sugar degradation.
Definitions:
Odor threshold - minimum detectable quantity via nasal
perception.
Taste threshold - minimum detectable quantity via retronasal
perception.
Odor Activity Value (OAV) - ratio of the concentration
of a molecule to its odor threshold.
Flavor dilution factor - when high signifies a key odorant.
Sources
Clarke, R. J. The Flavour of Coffee. In
Dev. Food Science. 3 B. 1986. 1-47.
Blank, I.; Sen, A.; and Grosch, W. 14th
ASIC Colloq. San Francisco. 1991. 117-129.
Grosch, W. 16th ASIC Colloq. Kyoto. 1995.
147-156.
Illy, A. and Viani, Rinantonio. Espresso
Coffee: The Chemistry of Quality.