Coffee Chemistry: Coffee Aroma
                    Coffee aroma  is responsible for all coffee
                      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 coffee 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 causing 
                      a dramatic decrease in the overall coffee flavor.
                    Perception of Coffee Aroma 
                    Coffee aroma is perceived by two different mechanisms. It can 
                      either be sensed nasally via smelling the coffee through 
                      the nose or 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 coffee 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 coffee elements 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 chemical processses that affect 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 aromatic compounds in coffee  
                          as summarized by Grosch. Click on compound name for 
                          more information. | 
                      
                    
                     
                      
                        
                            
                           
                            | Volatile1 | 
                            Conc.
                              (mg/L)1 | 
                            OAV1 | 
                            Coffee 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 aromatic 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.