Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits
Abstract
:1. Introduction
2. Results and Discussion
2.1. Identification of An Unknown “Spicy, Woody, Incense” Odorant in Oak Wood
2.2. Quantitation of Rotundone
2.3. Relative Potency of Rotundone in Bourbon Whiskey
2.3.1. Identification of Potent Odorants in Bourbon Whiskeys of Increasing Age (4, 8, and 12 Years) by Aroma Extract Dilution Analysis (AEDA)
2.3.2. Concentrations and OAVs of Selected Potent Odorants in Bourbon Whiskeys of Increasing Age (4, 8, and 12 Years)
3. Materials and Methods
3.1. Chemicals and Reference Standards
3.2. Materials
3.3. Analysis of Oak Wood Extracts
3.3.1. For Identification of Odorants
3.3.2. For Identification of “Spicy, Woody, Incense-Like” Unknown Odorant in Oak Extracts
3.3.3. Multidimensional GC–MS–O
3.4. GC–O Analysis of Distilled Spirits
3.4.1. Direct Solvent Extraction
3.4.2. Aroma Extract Dilution Analysis (AEDA)
3.4.3. Gas Chromatography–Olfactometry–Mass Spectrometry (GC–MS–O)
3.4.4. Compound Identification
3.5. Quantitative Analysis of Selected Compounds by Stable Isotope Dilution Analysis (SIDA)
3.5.1. Headspace Solid-Phase Microextraction GC–MS Method
3.5.2. Direct Solvent Extraction (DSE)–GC–MS Method
3.5.3. Direct Injection GC–MS Method
3.6. Statistical Analysis
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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Compound | Odor Description | RI (Rtx-5) b | Detected by G–CO | |
---|---|---|---|---|
French | American | |||
hexenal | green, cut-grass | 811 | + | + |
heptanal | citrus, orange | 904 | + | + |
unknown | earthy, mushroom | 912 | + | |
3-octanol | mushroom | 982 | + | + |
o-cresol c | creosote, inky | 1062 | + | |
p-cresol c | barnyard, bandaid | 1083 | + | |
guaiacol | smokey | 1085 | + | + |
4-hydroxy-2,5-dimethyl-3(2H)-furanone c | caramel, burnt sugar | 1096 | + | + |
dihydromaltol c | caramel | 1101 | + | |
maltol c | caramel | 1110 | + | |
3-hydroxy-4,5-dimethyl-2(5H)-furanone c | curry, maple | 1114 | + | |
(Z)-2-nonenal | hay/stale | 1149 | + | + |
(E,Z)-2,6-nonadienal | melon, cucumber | 1156 | + | + |
(E)-2-nonenal | hay/stale | 1161 | + | + |
(E,E)-2,4-nonadienal | fatty, fried | 1217 | + | |
(E)-oak lactone | herbaceous, coconut | 1294 | + | + |
4-ethylguaiacol | smokey, cloves | 1274 | + | + |
thymol | woody, thyme | 1293 | + | |
p-vinylguaiacol | smokey, cloves | 1321 | + | + |
(Z)-oak lactone | herbaceous, coconut | 1331 | + | + |
Syringol | smokey | 1356 | + | + |
(E)-2-undecenal c | fresh, fatty, cilantro | 1366 | + | |
eugenol | spicy, cloves | 1362 | + | + |
γ-nonalactone | fruity, peach | 1368 | + | |
vanillin | vanilla | 1392 | + | + |
γ-decalactone | fruity, peach | 1463 | + | |
(E)-isoeugenol | spicy, cloves | 1463 | + | + |
(Z)-6-dodecen-γ-lactone | creamy, dairy | 1665 | + | + |
δ-decalactone | floral, peach, coconut | 1501 | + | |
unknown | spicy, woody, incense | 1724 | + | + |
Product | Concentration (µg/L, ppb) a | % RSD b |
---|---|---|
Jim Beam Bourbon (4 year) (JB 4) | 0.342 c | 0.54 c |
Jim Beam Black Bourbon (8 year) (JB 8) | 0.403 c | 1.4 c |
Jim Beam Signature Craft (12 year) (JB 12) | 0.453 c | 1.9 c |
Bulleit Bourbon (~6 year) | 0.694 | 0.12 |
Bulleit Bourbon 10 (10 year) | 1.35 | 0.85 |
W.L Weller Bourbon (12 year) | 0.393 | 1.8 |
Elijah Craig Bourbon (12 year) | 0.694 | 10 |
Bulleit Rye Whiskey (~4 year) | 0.434 | 0.58 |
Jack Daniels Tennessee Whiskey | 0.166 | 0.10 |
Johnnie Walker Black Label Scotch Whiskey (~12 year) | 0.150 | 2.2 |
Appleton Estates Extra Rum (12 year) | 0.152 | 1.8 |
Don Julio Añejo Tequila (18 month) | 0.307 | 0.85 |
Milagro Silver Tequila | 0.100 | 1.1 |
Compound | Odor Description | RI a | Log3 FD b | ||||||
---|---|---|---|---|---|---|---|---|---|
JB 4 | JB 8 | JB 12 | |||||||
Wax | Rtx5 | Wax | Rxt5 | Wax | Rtx5 | Wax | Rtx5 | ||
vanillin | vanilla | 2529 | 1413 | 6 | 5 | 7 | 5 | 8 | 5 |
(Z)-whiskey lactone | herbaceous, coconut | 1949 | 1329 | 5 | 5 | 8 | 6 | 8 | 6 |
syringol | smokey | 2241 | 1355 | 7 | 4 | 8 | 5 | 7 | 5 |
2/3-methyl-1-butanol | chocolate, malty | 1212 | 836 | 8 | 5 | 7 | 5 | 7 | 5 |
2-phenethyl alcohol | rosey, wine-like | 1900 | 1120 | 6 | 4 | 6 | 5 | 7 | 4 |
guaiacol | smokey | 1854 | 1087 | 7 | 4 | 7 | 5 | 7 | 4 |
(E)-isoeugenol | spicy, cloves | 2335 | 1459 | 6 | 3 | 6 | 3 | 6 | 4 |
eugenol | spicy, cloves | 2154 | 1361 | 5 | 4 | 5 | 4 | 6 | 3 |
(E)-β-damascenone | floral, cooked apple | 1823 | 1391 | 4 | 4 | 5 | 4 | 4 | 4 |
ethyl hexanoate | fruity, berry | 1245 | 1001 | 4 | 3 | 4 | 3 | 4 | 5 |
acetal | fruity | 927 | 728 | 4 | 4 | 4 | 4 | 4 | 4 |
ethyl 2-methylbutanoate | fruity, berry | 1070 | 857 | 3 | 3 | 4 | 3 | 4 | 4 |
ethyl butanoate | fruity, bubble gum | 1046 | 808 | 3 | 2 | 3 | 3 | 4 | 4 |
(Z)-2-nonenal c | hay, stale | 1505 | 1149 | 2 | 2 | 3 | 2 | 4 | 3 |
syringaldehyde | smokey, vanilla | 2884 | 1671 | 4 | 3 | 4 | 3 | 3 | 3 |
ethyl vanillate | spicy | 2642 | 1580 | 3 | 1 | 3 | 2 | 3 | 1 |
rotundone | spicy, woody, incense | 2262 | 1720 | 2 | 2 | 4 | 4 | 3 | 3 |
4-ethylphenol | barnyard, bandaid | 2167 | 1180 | 1 | 1 | 1 | 3 | 3 | 1 |
γ-nonalactone | fruity, peach | 2020 | 1370 | 3 | 2 | 3 | 3 | 3 | 2 |
2-phenethyl acetate | floral, rosy | 1812 | 1258 | 3 | 1 | 3 | 1 | 3 | 1 |
ethyl octanoate | fruity | 1428 | 1193 | 3 | 1 | 3 | 1 | 3 | 2 |
2-methyl-1-propanol | chocolate, malty | 1099 | 634 | 1 | ND | 1 | ND | 3 | ND d |
2/3-methylbutanoic acid c | sweaty | 1662 | 3 | ND | 3 | ND | 3 | ND | |
3-methylbutyl acetate | fruity, banana | 1147 | 875 | <1 e | 1 | <1 | 1 | 2 | 2 |
unknown | fruity | 1198 | 1 | <1 | 1 | ND | 2 | ND | |
2-acetyl-1-pyrroline c | roasty, cereal | 1314 | 1052 | 2 | 1 | 1 | 1 | 2 | 2 |
acetic acid | pungent, vinegar | 1444 | 832 | 1 | ND | <1 | ND | 2 | 1 |
(E)-2-nonenal c | hay, stale | 1537 | 1164 | 1 | <1 | 2 | 1 | 2 | 1 |
butyric acid | cheesy | 1619 | 853 | 2 | 1 | 2 | <1 | 2 | 2 |
(E,E)-2,4-nonadienal | fatty, fried | 1700 | 1157 | 2 | <1 | 1 | 1 | 2 | 2 |
unknown | cereal/burnt | 1801 | 1050 | 2 | 1 | 4 | <1 | 4 | 2 |
(E)-whiskey lactone | coconut | 1882 | 1291 | 2 | 1 | 2 | 1 | 2 | 2 |
4-vinylguaiacol c | smokey, spicy | 2174 | 1320 | 2 | ND | 1 | 1 | 2 | 2 |
unknown | soapy | 2456 | 1555 | 1 | ND | 1 | <1 | 2 | <1 |
p-cresol | barnyard, bandaid | 2074 | 1109 | 1 | 1 | <1 | 3 | 1 | 3 |
(Z)-6-dodeceno-γ-lactone c | creamy, diary | 2384 | 1666 | 1 | <1 | <1 | ND | 1 | 1 |
1-octen-3-one c | metallic, mushroom | 1306 | 982 | 1 | ND | <1 | 1 | <1 | 2 |
γ-decalactone c | fruity, peach | 2139 | 1465 | ND | ND | ND | ND | <1 | <1 |
β-ionone c | floral, violet | 1427 | ND | ND | ND | <1 | ND | <1 | |
4-ethyl guaiacol c | smokey, spicy | 1994 | 1283 | <1 | ND | <1 | ND | <1 | 2 |
Compound | Concentration (µg/L, ppb) | Sig.a | ||
---|---|---|---|---|
Jim Beam Bourbon (4 Year) | Jim Beam Black Bourbon (8 Year) | Jim Beam Signature Craft (12 Year) | ||
3-methyl-1-butanol | 962,000 (±4.0%) | 1,090,000 (±4.5%) | 1,420,000 (±4.9%) | 0.97 |
2-methyl-1-butanol | 379,000 (±4.3%) | 462,000 (±4.1%) | 727,000 (±4.5%) | 0.96 |
2-methyl-1-propanol | 224,000 (±4.4%) | 321,000 (±8.5%) | 419,000 (±8.6%) | 1.0 |
2-phenethyl alcohol | 33,800 (±0.40%) | 41,700 (±1.4%) | 39,100 (±1.4%) | * |
syringaldehyde | 7530 (±3.5%) | 10,400 (±0.54%) | 14,400 (±3.0%) | 1.0 |
acetal | 5390 (±3.7%) | 5360 (±5.6%) | 5170 (±0.49%) | * |
ethyl octanoate | 4790 (±5.2%) | 3260 (±1.8%) | 5830 (±3.0%) | * |
(Z)-whiskey lactone | 2850 (±2.1%) | 4330 (±2.3%) | 5470 (±1.8%) | 1.0 |
3-methylbutyl acetate | 1910 (±0.66%) | 973 (±2.7%) | 1980 (±1.9%) | * |
ethyl hexanoate | 1500 (±2.8%) | 1420 (±1.5%) | 3110 (±2.8%) | * |
4-ethyl phenol | 72.7 (±0.71%) | 58.4 (±0.82%) | 91.2 (±9.1%) | * |
vanillin | 619 (±2.3%) | 950 (±2.9%) | 1410 (±1.9%) | 1.0 |
2-phenethyl acetate | 614 (±1.3%) | 123 (±1.7%) | 211 (±0.74%) | * |
ethyl butyrate | 458 (±1.0%) | 740 (±2.2%) | 1260 (±2.6%) | 0.99 |
guaiacol | 39.1 (±7.6%) | 56.7 (±4.8%) | 63.5 (±4.3%) | 0.97 |
(E)-whiskey lactone | 316 (±0.48%) | 457 (±0.81%) | 586 (±2.3%) | 1.0 |
(E)-isoeugenol | 306 (±2.4%) | 368 (±3.5%) | 416 (±7.7%) | 1.0 |
eugenol | 207 (±3.9%) | 197 (±2.0%) | 131 (±5.3%) | −0.920 |
syringol | 205 (±14%) | 265 (±20%) | 219 (±4.8%) | * |
γ-nonalactone | 145 (±13%) | 190 (±3.7%) | 175 (±14%) | * |
ethyl vanillate | 127 (±14%) | 299 (±3.9%) | 572 (±17%) | 0.99 |
ethyl 3-methylbutanoate | 85.0 (±1.0%) | 183 (±3.1%) | 313 (±11%) | 0.99 |
p-cresol | 18.0 (±4.0%) | 26.9 (±26%) | 23.6 (±7.8%) | * |
(E)-β-damascenone | 6.56 (±2.1%) | 3.58 (±2.6%) | 3.62 (±2.1%) | * |
rotundone | 0.342 (±0.54%) | 0.403 (±1.4%) | 0.453 (±1.9%) | 1.0 |
Compound | ODT (µg/L, ppb) a | Odor-Activity Value b | ||
---|---|---|---|---|
Jim Beam Bourbon (4 Year) | Jim Bean Black Bourbon (8 Year) | Jim Beam Signature Craft (12 Year) | ||
ethyl 3-methylbutanoate | 1.6 [35] | 53 | 114 | 195 |
ethyl butanoate | 9.5 [35] | 48 | 78 | 133 |
ethyl hexanoate | 30 [35] | 50 | 47 | 104 |
(E)-isoeugenol | 6 [39] c | 51 | 61 | 69 |
(Z)-whiskey lactone | 67 [4] | 43 | 65 | 82 |
guaiacol | 9.2 [35] | 43 | 61 | 69 |
rotundone | 0.008 [7] d | 43 | 50 | 57 |
vanillin | 22 [35] | 28 | 43 | 64 |
ethyl octanoate | 147 [35] | 33 | 22 | 40 |
(E)-β-damascenone | 0.14 [35] | 47 | 26 | 26 |
eugenol | 7.1 [35] | 29 | 28 | 18 |
2-phenylethanol | 2600 [35] | 13 | 16 | 15 |
γ-nonalactone | 21 [35] | 6.9 | 9.0 | 8.3 |
3-methylbutylacetate | 245 [35] | 7.8 | 4.0 | 8.1 |
acetal | 719 [35] | 7.5 | 7.5 | 7.2 |
2-methyl-1-propanol | 101,000 [40] | 2.2 | 3.2 | 4.1 |
2-methyl-1-butanol | 212,000 [35] | 1.8 | 2.2 | 4.1 |
3-methyl-1-butanol | 561,000 [35] | 1.7 | 1.9 | 2.5 |
2-phenylethyl acetate | 108 [35] | 5.7 | 1.1 | 2.0 |
(E)-whiskey lactone | 790 [4] | 0.40 | 0.58 | 0.74 |
4-ethylphenol | 170 [35] | 0.43 | 0.34 | 0.54 |
syringol | 580 [41] | 0.35 | 0.46 | 0.38 |
p-cresol | 81.6 [42] | 0.22 | 0.33 | 0.29 |
syringaldehyde | 50,000 [43] c | 0.15 | 0.21 | 0.29 |
ethyl vanillate | 900 [44] c | 0.14 | 0.33 | 0.64 |
Method | Target | Labeled IS | Mass IS (µg) | Sample (mL) | Response Factor, Rf (iontarget vs. ionIS) |
---|---|---|---|---|---|
SPME (3.5.1) | acetal | [2H8]-ethyl acetate | 243 | 1.0 | 0.521 (103 vs. 96) |
ethyl butanoate | [2H5]-ethyl butanoate | 1.51 | 1.0 | 0.771 (88 vs. 93) | |
ethyl hexanoate | [2H5]-ethyl hexanoate | 2.50 | 1.0 | 0.831 (88 vs. 93) | |
ethyl octanoate | [2H5]-ethyl octanoate | 2.10 | 1.0 | 0.797 (88 vs. 93) | |
ethyl 3-methylbutanoate | [2H5]-ethyl 3-methyl butanoate | 0.797 | 1.0 | 0.834 (88 vs. 93) | |
ethyl vanillate | [2H5]-ethyl vanillate | 0.168 | 1.0 | 0.954 (196 vs. 201) | |
3-methylbutyl acetate | 3-methylbutyl [2H3]-acetate | 3.89 | 1.0 | 0.834 (87 vs. 90) | |
2-phenylethyl acetate | [1,2-13C2]-2-phenylethyl acetate | 0.111 | 1.0 | 0.932 (104 vs. 106) | |
2-phenylethanol | [13C2]-2-phenylethanol | 41.4 | 1.0 | 1.00 (122 vs. 124) | |
β-damascenone | [2H4]-β-damascenone | 0.0352 | 1.0 | 0.468 (190 vs. 194) | |
DSE (3.5.2) | (E)-whiskey lactone | [2H2]-(E)-whiskey lactone | 3.37 | 1.0 | 0.827 (99 vs. 101) |
(Z)-whiskey lactone | [2H2]-(Z)-whiskey lactone | 3.57 | 1.0 | 0.546 (99 vs. 101) | |
γ-nonalactone | [2H2]-γ-nonalactone | 0.204 | 1.0 | 1.11 (85 vs. 87) | |
guaiacol | [2H3]-guaiacol | 5.35 | 10.0 | 1.02 (124 vs. 127) | |
p-cresol | [2H8]-p-cresol | 0.306 | 10.0 | 0.552 (107 vs. 113) | |
4-ethylphenol | [2H5]-4-ethylphenol | 2.30 | 10.0 | 0.845 (122 vs. 127) | |
syringol | [2H3]-syringol | 13.3 | 10.0 | 0.933 (154 vs. 157) | |
eugenol | [2H3]-eugenol | 2.40 | 10.0 | 0.611 (164 vs. 167) | |
(E)-isoeugenol | [2H3]-(E)-isoeugenol | 2.44 | 10.0 | 0.932 (164 vs. 167) | |
vanillin | [2H3]-vanillin | 24.6 | 10.0 | 0.974 (152 vs. 155) | |
syringaldehyde | [2H3]-syringaldehyde | 175 | 10.0 | 0.611 (182 vs. 185) | |
rotundone | [2H4]-rotundone | 0.0104 | 10.0 | 0.998 (218 vs. 206) | |
Direct injection (3.5.3) | 2-methyl-1-propanol | [2H7]-2-methyl-1-propanol | 15.0 | 0.10 | 0.956 (74 vs. 81) |
2-methyl-1-butanol | [2H11]-3-methyl-1-butanol | 15.8 | 0.10 | 0.963 (57 vs. 62) | |
3-methyl-1-butanol | 0.833 (55 vs. 62) |
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Genthner-Kreger, E.; Cadwallader, K.R. Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits. Molecules 2021, 26, 4368. https://doi.org/10.3390/molecules26144368
Genthner-Kreger E, Cadwallader KR. Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits. Molecules. 2021; 26(14):4368. https://doi.org/10.3390/molecules26144368
Chicago/Turabian StyleGenthner-Kreger, Elizabeth, and Keith R. Cadwallader. 2021. "Identification of Rotundone as an Important Contributor to the Flavor of Oak-Aged Spirits" Molecules 26, no. 14: 4368. https://doi.org/10.3390/molecules26144368