Identification and Quantification of Volatile Compounds Found in Vinasses from Two Different Processes of Tequila Production
Abstract
:1. Introduction
2. Results
2.1. Identification and Concentration of Volatile Compounds
2.1.1. Organic Acids
2.1.2. Esters
2.1.3. Alcohols
2.1.4. Aldehydes
2.1.5. Alkanes
2.1.6. Furanic Compounds
2.1.7. Ketones
2.1.8. Phenols
2.1.9. Pyrans
2.2. Principal Component Analysis (PCA)
3. Discussion
3.1. Organic Acids
3.2. Esters
3.3. Alcohols
3.4. Aldehydes
3.5. Alkanes
3.6. Furanic Compounds
3.7. Ketones
3.8. Phenol Compounds
3.9. Pyrans
3.10. Relationship between PCA and Not-Cooking (NC) and Cooking (C) Processes
4. Materials and Methods
4.1. Chemicals and Standards Used
4.2. Samples
4.3. Volatile Compound Extractions
4.4. Separation and Identification of Volatile Compounds
4.5. Statistical Analysis
5. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Number | Compound | Retention Time (min) | Odor Quality a | Kovats Retention Index b | Sample Found | Identification c | Reference |
---|---|---|---|---|---|---|---|
Acids | |||||||
1 | Acetic acid | 11.89 | sour, astringent, viniegra | 1680 b | All samples | MS, IK, STD | Wanakhachornkrai & Lertsiri (2003) |
2 | Isobutyric acid | 14.48 | rancid, butter, cheese, hammy | ˃1500 b | NC1, NC2, NC3, C1, C3 | MS, IK | Chuenchomrat et al. (2008) |
3 | Butyric acid | 16.06 | - | 1720 b | All samples | MS, IK, STD | Wanakhachornkrai & Lertsiri (2003) |
4 | Isovaleric acid | 16.43 | sweat, acid, rancid | 1864 b | All samples | MS, IK, STD | Jerković et al. (2012) |
5 | Valeric acid | 19.4 | sweet | - | NC2 | MS, IK, STD | Chung et al. (1993) |
6 | Caproic acid | 22.5 | cheese, oil, pungent, sour, rancid, sickening | - | All samples | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
7 | Oenanthic acid | 25.82 | rancid, sour, sweat | - | NC2 | MS | - |
8 | Caprylic acid | 29.09 | cheese, fat, grass, oil | - | NC1, NC2, NC3, C1, C3 | - | - |
9 | Benzoic acid, hexahydro- | 29.79 | fruit | - | NC2 | MS | - |
10 | 9-Decenoic acid | 37.15 | - | - | NC2 | MS | - |
11 | Hendecanoic acid | 41.25 | oil | - | NC1, NC3 | MS | - |
12 | Lauric acid | 41.5 | metal | - | NC2 | MS | - |
13 | 3-Methyl-benzoic acid | 42.56 | - | - | All samples | MS | - |
14 | Benzenepropanoic acid | 44.48 | - | - | NC2, C2 | MS | - |
15 | Palmitic acid | 51.775 | - | - | All samples | MS | - |
16 | Myristic acid | 57.6 | - | - | All samples | MS | - |
Esters | |||||||
17 | Ethyl orthoformate | 7.07 | - | 1465 b | NC2, C2 | MS | - |
18 | Ethyl butanoate | 8.88 | - | ˃1493 b | C2 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
19 | 1,1-Dimethylpropyl ester, pentanoic acid | 9.38 | sweet | ˃1500 b | NC1, NC3 | MS | - |
20 | Ethyl lactate | 9.88 | pungent, rancid, soy | - | NC2, C1, C2, C3 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
21 | Methylthiohexanoate | 17.11 | - | ˃1500 b | NC2 | MS | - |
22 | Diethyl succinate | 17.4 | - | - | NC2 | MS | - |
23 | Ethyl acetate | 19.37 | aromatic, brandy, grape | - | C2 | MS, IK | - |
24 | Methyl salicylate | 20.43 | - | - | NC2 | MS | - |
25 | Allyl phenylacetate | 21.62 | floral | - | C2 | MS | - |
26 | Ethyl palmitate | 34.65 | - | - | NC1, NC2, NC3, C1, C3 | MS | - |
27 | 2-Phenylethyl acetate | 35.4 | flower, honey, rose | - | NC1, NC3 | MS | - |
28 | Monoethyl succinate | 38.62 | - | - | NC1, NC2, NC3, C1, C3 | MS | - |
Alcohols | |||||||
29 | 2-Methyl-1-propanol | 6.36 | apple, bitter, cocoa, wine | 1107 b | NC1, NC3 | MS, IK | Chuenchomrat et al. (2008) |
30 | 3,7-Dimethyl-1-octanol | 6.57 | - | - | NC1, NC3 | MS | - |
31 | 1-Butanol | 7.21 | fruit | 1156 b | NC2 | MS, IK | Chuenchomrat et al. (2008) |
32 | 3-Penten-2-ol | 7.56 | - | - | All samples | MS | - |
33 | 2-Butyl-1-Octanol | 9.26 | - | - | NC1, NC3, C1, C2, C3 | MS | - |
34 | 3-Ethoxy-1-propanol | 10.37 | - | - | C2 | MS | - |
35 | 2-Ethyl-1-hexanol | 12.52 | - | ˃1361 b | C2 | MS, IK | Chung et al. (1993) |
36 | 1-Decanol, 2-hexyl- | 13.50 | - | - | NC2 | MS | - |
37 | 2,3-Butanediol | 14.69 | - | ˃1493 b | All samples | MS, IK | Chuenchomrat et al. (2008) |
38 | 1,2-Propanediol | 15.1 | - | - | NC2, C1, C2 | MS | - |
39 | Furfuryl alcohol | 17.13 | burnt, caramel, cooked | ˃1493 b | All samples | MS, IK, STD | Chuenchomrat et al. (2008) |
40 | 3-(Methylthio)-1-propanol | 18.65 | - | - | C1, C2 | MS | - |
41 | 1,3-Propanediol | 20.67 | - | - | C2 | MS | - |
42 | Benzyl alcohol | 23.54 | sweet, flowery, boiled cherries, moss, roasted bread, rose | 1943 b | All samples | MS, IK | Chuenchomrat et al. (2008) |
43 | Phenylethyl Alcohol | 24.58 | honey, spice, rose, flowery, caramel | 1997 b | All samples | MS, IK | Jerković et al. (2012) |
44 | Benzene propanol | 28.66 | - | - | All samples | MS | - |
45 | p-Menthane-1,8-diol | 30.17 | - | - | NC1, NC3 | MS | - |
46 | 1-(2-Furanyl)-1,2-ethanediol | 44.03 | - | - | All samples | MS | - |
47 | 1-Phenyl-1-decanol | 58.78 | - | - | NC1, NC3 | MS | - |
48 | 3-(p-Hydroxyphenyl)-1-propanol | 58.99 | - | - | NC2 | MS | - |
Aldehydes | |||||||
49 | Benzaldehyde | 13.63 | bitter almond, burnt sugar, cherry, malt, roasted pepper | ˃1500 b | C1, C3 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
50 | 4-Methyl-benzaldehyde | 16.8 | - | ˃1500 b | NC1, NC2, NC3 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
51 | 3-Methyl-benzaldehyde | 37.35 | - | ˃1500 b | NC1, NC3, C2 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
Alkanes | |||||||
52 | Dodecane | 7.823 | - | - | All samples | MS | - |
53 | 4,6-Dimethyl-dodecane | 7.90 | - | 1200 b | C1, C3, NC1, NC3 | MS, IK | Chung et al. (1993) |
54 | 2,3,6,7-Tetramethyl-octane | 8.064 | - | 1300 b | C1, C3 | MS, IK | Chung et al. (1993) |
55 | 5-Methyl-tridecane | 9.67 | - | - | NC1, NC3, C1, C3 | MS | - |
56 | Tetradecane | 10.54 | - | 1400 b | All samples | MS, IK | Jerković et al. (2012) |
57 | 3,3-Dimethyl-heptane | 10.61 | - | - | NC1, NC3 | MS | - |
58 | Farnesan | 11.13 | - | - | NC1, NC3, C2 | MS | - |
59 | 3-Ethyl-3-methylheptane | 15.30 | - | - | All samples | MS | - |
60 | Nonadecane | 17.80 | - | 1900 b | All samples | MS, IK | Jerković et al. (2012) |
61 | Eicosane | 12.48 | - | 2000 b | All samples | MS, IK | Chung et al. (1993) |
Furanic | |||||||
62 | 2,2,3,3,4,4-Hexamethyltetrahydrofuran | 8.905 | - | - | C1, C3 | MS | - |
63 | Furfural | 12.30 | almond, baked potatoes, bread, burnt, spice | 1493 b | C1, C2, C3 | MS, IK, STD | Chuenchomrat et al. (2008) |
64 | 5-Methylfurfural | 12.38 | - | ˃1493 b | C1, C2, C3 | MS, IK | Chuenchomrat et al. (2008) |
65 | Acetylfuran | 13.20 | balsamic, cocoa, coffee | - | C1, C3 | MS | - |
66 | 2-Furoate-methyl | 14.88 | fruit | - | All samples | MS, STD | - |
67 | Furan, 2-(1,2-diethoxyethyl)- | 21.07 | - | - | All samples | MS, IK | - |
68 | 2-(Hydroxyacetyl)furan | 27.83 | - | - | NC1, NC3 | MS | - |
69 | 2,5-Dimethyl-2-(2-tetrahydrofuryl) tetrahydrofuran | 30.37 | - | - | All samples | MS | - |
70 | HMF | 41.99 | almond, baked potatoes, bread, burnt, spice | ˃1493 b | C1, C2, C3 | MS, IK, STD | Chuenchomrat et al. (2008) |
71 | Furan, 2-(1,2-dimethoxyethyl)- | 32.16 | - | - | NC2 | MS | - |
72 | Furan, 2-ethoxy-4-ethyl-2,3-dihydro | 36.04 | - | - | C1, C3 | MS | - |
Ketones | |||||||
73 | 3(2H)-Furanone, dihydro-2-methyl | 8.8 | nuts | 1207 b | C1, C2, C3 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
74 | Acetoin | 9.057 | butter, creamy, green pepper | 1306 b | NC1, NC2, C1, C2, C3 | MS, IK | Chuenchomrat et al. (2008) |
75 | 2-Cyclopenten-1-one | 10.26 | - | - | C1, C3 | MS | - |
76 | 2-Butanone, 3,4-epoxy-3-ethyl | 13.18 | - | - | NC2 | MS | - |
77 | 2(3H)-Furanone, dihydro-5-methyl- | 15.87 | - | ˃1500 b | NC2, C1, C2, C3 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
78 | γ-Butyrolactone | 16.394 | caramel, cheese, roasted nut | 1610 b | NC1, NC2, NC3, C1, C2,C3 | MS, IK | Márquez et al. (2010) |
79 | 2-Cyclopenten-1-one, 2-hydroxy-3-methyl | 22.04 | - | - | C1, C2, C3 | MS | - |
80 | α, β-Angelica lactone | 17.75 | floral | - | C1, C2 | MS, IK | - |
81 | 2,5-Dimethyl-4-hydroxy-3(2H)-furanone | 22.96 | burnt, caramel, cotton candy, honey | 2024 b | C1, C3 | MS, IK | Fuhrmann & Grosch (2002) |
82 | Furyl hydroxymethyl ketone | 27.51 | - | - | NC3, C1, C2, C3 | MS | - |
83 | 2(3H)-Furanone, dihydro-3-hydroxy-4,4-dimethyl | 28.34 | - | - | C1, C3 | MS | - |
84 | Ethanone, 1-(2,6-dihydroxy-4-methoxyphenyl) | 39.39 | - | - | NC2 | MS | - |
85 | Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl) | 54.24 | - | - | NC2 | MS | - |
Phenols | |||||||
86 | p-Guaiacol | 23.06 | burnt, phenol, wood | ˃1500 b | NC2 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
87 | p-Methylguaiacol | 26.06 | phenol | ˃1500 b | NC2 | MS, IK | Wanakhachornkrai & Lertsiri (2003) |
88 | 3-Methyl phenol | 29.93 | - | - | NC2 | MS | - |
89 | Phenol, 2-methyl-5-(1-methylethyl) | 32.31 | caraway, spice, thyme | 2189 b | NC2 | MS, IK | Jerković et al. (2012) |
90 | 2,4-Di-tert-butylphenol | 36.67 | - | - | All samples | MS | - |
91 | Phenol, 2-(5-isoxazolyl) | 45.90 | - | - | NC2 | MS | - |
92 | Eugenol | 45.31 | burnt, clove, spice | - | NC2 | MS, STD | - |
93 | Phenol, 2-(2-methylpropyl) | 51.53 | - | - | NC2 | MS | - |
94 | 4-(2-Hydroxyethyl) phenol | 54.59 | - | - | C1, C3 | MS | - |
Pyrans | |||||||
95 | 2H-Pyran-2,6(3H)-dione | 27.26 | - | - | NC1, NC3 | MS | - |
96 | 2-Pentoxy-tetrahydropyran | 28.10 | - | - | NC1, NC3 | MS | - |
97 | 4H-Pyran-4-one, 2,3-dihydro-3,5-dihydroxy-6-methyl | 35.27 | - | - | NC1, NC2, NC3 | MS | - |
98 | Pyrrolo[1,2-a] pyrazine-1,4-dione, hexahydro-3-(2-methylpropyl) | 60.62 | - | - | C1, C2, C3 | MS | - |
Others | |||||||
99 | m-Dioxane, 2-methyl | 5.96 | - | - | C2 | MS | - |
100 | p-Dichlorobenzene | 11.78 | - | - | NC1, NC3 | - | |
101 | m-Di-tert-butylbenzene | 11.28 | - | - | C1, C2, C3 | MS | - |
102 | 6,7-Dihydro-7-hydroxylinalool | 26.69 | - | - | NC1, NC3 | MS | - |
103 | 4-Acetoxy-3-methoxystyrene | 33.29 | - | - | NC1, NC3 | MS | - |
104 | Ethyl linoleate | 60.85 | - | - | All samples | MS | - |
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Rodríguez-Félix, E.; Contreras-Ramos, S.M.; Davila-Vazquez, G.; Rodríguez-Campos, J.; Marino-Marmolejo, E.N. Identification and Quantification of Volatile Compounds Found in Vinasses from Two Different Processes of Tequila Production. Energies 2018, 11, 490. https://doi.org/10.3390/en11030490
Rodríguez-Félix E, Contreras-Ramos SM, Davila-Vazquez G, Rodríguez-Campos J, Marino-Marmolejo EN. Identification and Quantification of Volatile Compounds Found in Vinasses from Two Different Processes of Tequila Production. Energies. 2018; 11(3):490. https://doi.org/10.3390/en11030490
Chicago/Turabian StyleRodríguez-Félix, Elizabeth, Silvia Maribel Contreras-Ramos, Gustavo Davila-Vazquez, Jacobo Rodríguez-Campos, and Erika Nahomy Marino-Marmolejo. 2018. "Identification and Quantification of Volatile Compounds Found in Vinasses from Two Different Processes of Tequila Production" Energies 11, no. 3: 490. https://doi.org/10.3390/en11030490