An Overview on Truffle Aroma and Main Volatile Compounds
Abstract
:1. Introduction
1.1. History
1.2. Cultivation
1.3. Uses
1.4. Tracing Truffles in the Soil and Interactions with Mammals
2. Truffle Aroma Characterization: Black Truffle and White Truffle
2.1. Aroma Profiles of Truffles
2.2. Factors Influencing Truffle Aroma
2.3. Major Truffle Aroma Components
No | Compound Name and Class | Odor Description | Content [%] | References | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Black Truffles | White Truffles | ||||||||||||
T. mel | T. aest | T. ind | T. mac | T. mes | T. ruf | T. bru | T. mag | T. exc | T. bor | ||||
1 | Sulfur compounds Dimethyl sulfide | Rotten, cabbage | 0.52, 57.0 | 1.04, 0.26 | 8.3 | 2.95, 4.44 | [31,42,52,53,71] | ||||||
2 | bis(Methylthio)methane (=2,4-Dithiapentane) | sulfuric, garlic | 67.33, 83.71, 67.8 | [52,65,71] | |||||||||
3 | Methyl (methylthio)methyl disulfide | 0.05, 0.06 | [52,71] | ||||||||||
4 | Dimethyl disulfide | Cabbage, onion | 0.04, 0.17 | 0.06 | 0.15 | [31,53,71] | |||||||
5 | Dimethyl trisulfide | Rotten food | 0.07, 0.01 | 0.18 | 0.02 | [31,53,71] | |||||||
6 | Sulfinylbismethane | 0.04 | 0.05 | [31] | |||||||||
7 | Methanethiol | Cabbage, vegetal | 0.17 | 0.010 | [53,71] | ||||||||
8 | tris(Methylthio)methane | 0.29 | [71] | ||||||||||
9 | 3-Methyl-4,5-dihydrothiophene | Onion, savory, roast, truffle, garlic, butter | 4.87 | [48] | |||||||||
10 | 2-Methyl-4,5-dihydrothiophene | Aged cheese, rubber | 0.34 | [48] | |||||||||
11 | DMTS = (methyltrisulfanyl)methane | Truffle, onion, garlic | 0.04 | [48] | |||||||||
12 | Methional | Boiled potatoes | 0.12 | [53] | |||||||||
13 | Dimethylsulphoxide | Cheesy, garlic, mushroom | 0.33 | [53] | |||||||||
14 | (E)-1-Methylsulfanylprop-1-ene | Acrid strong garlic-like | 0.2 | 27.0 | 0.3 | 29.6 | [65] | ||||||
15 | 1-Methylsulfanylpropane | Alliaceous creamy leek | 0.1 | 22.1 | 0.4 | [65] | |||||||
16 | Methylsulfanylmethane | 11.7 | 18.9 | 4.3 | 1.3 | 1.2 | 8.2 | 4.5 | 14.6 | 4.9 | [65] | ||
17 | (Z)-1-Methylsulfanylprop-1-ene | Acrid strong garlic-like | 8.0 | 0.2 | 6.7 | [65] | |||||||
18 | (Methyldisulfanyl)methane | 0.2 | 0.2 | 0.1 | 2.8 | 0.1 | [65] | ||||||
19 | 4-Mercapto-4-methyl-2-pentanone | 0.06 | [31] | ||||||||||
20 | Alcohols 1-Octen-3-ol | Mushroom, earthy | 4.04, 0.01,2.0 | 35.2, 1.8, 0.9 | 37.1, 0.2 | 4.7 | 9.6 | 3.1 | 11.2 | 0.09 | 2.4 | 2.51 | [31,42,48,52,53,65] |
21 | 2,6-Dimethyl-2-octanol | 0.26 | [52] | ||||||||||
22 | Z-5-Octen-1-ol | 2.8 | [42] | ||||||||||
23 | 3-Octanol | Earthy, mushroom, herbal | 0.05 | 4.03, 0.11 | 2.1 | [31,42,52] | |||||||
24 | 1-Octanol | Waxy, green, citrus | 0.41 | [52] | |||||||||
25 | 2-Butanol | 0.03 | 0.23, 6.3 | 0.3 | 0.1 | [31,65] | |||||||
26 | 6-Dodecanol | 1.48 | [31] | ||||||||||
27 | Octa-1,5-dien-3-ol | 0.19 | 0.32 | [31] | |||||||||
28 | 1-Hexanol | Alcoholic, pungent, green | 0.07 | 0.51 | [31] | ||||||||
29 | 2-Ethyl-1-hexanol | 0.02 | 1.30 | [31] | |||||||||
30 | Ethanol | 0.06 | [71] | ||||||||||
31 | Isobutyl alcohol | 0.22 | [71] | ||||||||||
32 | 2-Methylbutan-1-ol | Malty | 4.94 | 4.7, 1.4, 3.7 | 0.6 | 3.2 | 0.4 | 3.70 | [31,52,65,71] | ||||
33 | 3-Methyl-1-butanol (Isoamyl alcohol) | Winey, onion, cheese | 41.9 | 13.9, 6.5 | 5.4 | 0.2 | 1.8 | 0.29 | [42,48,53,65] | ||||
34 | 2-Methyl-1-propanol | Winey | 0.31 | 0.59 | [31] | ||||||||
35 | 2,5-Dimethyl-3,4-hexanediol | 0.7 | [42] | ||||||||||
36 | Acids Nonanoic acid | 0.05 | [52] | ||||||||||
37 | Acetic acid | 3.17 | [31] | ||||||||||
38 | 2-Propenoic acid | 1.99 | [31] | ||||||||||
39 | 2-Methylhexanoic acid | 0.08 | 0.09 | [31] | |||||||||
40 | Esters Ethyl acetate | 0.04 | 0.47 | [31] | |||||||||
41 | Ethyl-3-methylbutanoate | Fruity, anise | 0.09 | 0.21 | [31,35] | ||||||||
42 | Butyl-2-methylbutanoate | 0.04 | [31] | ||||||||||
43 | 2-Methylpropyl 2-methylbutanoate | 0.29 | [31] | ||||||||||
44 | 2-Methylpropyl-3-methylbutanoate | 0.03 | [31] | ||||||||||
45 | 3-Methylbutyl-2-methylpropanoate | 0.27 | [31] | ||||||||||
46 | 2-Methylbutyl-2-methylbutanoate | 2.49 | [31] | ||||||||||
47 | Pentyl-3-methylbutanoate | 0.29 | [31] | ||||||||||
48 | sec-Butylformate | 1.80 | [42] | ||||||||||
49 | Ethyl 3-methylbutyrate | Fruit, anise | 0.03 | [35,42,53] | |||||||||
50 | Butan-2-yl formate | 15.70 | 11.40 | 0.20 | 2.20 | 7.00 | [65] | ||||||
51 | 2-Methylpropyl formate | 1.00 | 1.40 | 0.90 | [65] | ||||||||
52 | Aldehydes 2-Octenal | Green, citrus, fatty | 1.87 | 0.27, 8.27 | 0.13, 0.05 | [31,35,52,71] | |||||||
53 | Acetaldehyde | 0.07 | 0.28 | 0.12 | [31,71] | ||||||||
54 | Nonanal | Waxy, aldehydic, fatty | 0.12 | 1.16 | 0.07, 0.03 | [31,35,52,71] | |||||||
55 | Propanal | Vegetable, green | 0.24 | 0.89 | [31,71] | ||||||||
56 | 2-Methyl-butanal | Cocoa, almond-like | 19.13, 8.4 | 0.64, 0.1 | 2.0 | 0.4 | 0.8 | 0.57, 0.1 | [31,42,65,71] | ||||
57 | 3-Methyl-butanal | Green, nutty, cocoa | 38.31, 6.5 | 7.56, 1.2 | 3.2, 2.8 | 1.6 | 0.6 | 2.15, 1.5 | 0.8 | 0.37 | [31,42,48,65,71] | ||
58 | 2-Butenal | Green, vegetable | 3.45 | 7.90 | [31,35] | ||||||||
59 | Hexanal | Leafy, fruity, sweaty | 5.93 | 17.63 | 0.074 | [31,35,71] | |||||||
60 | 2-Methyl-2-butenal | Fruity, almond, nutty | 1.22 | 1.35 | [31,35] | ||||||||
61 | Heptanal | 0.16 | 5.36 | 0.05 | [31,71] | ||||||||
62 | Octanal | Waxy, orange, peel | 0.86 | 0.70 | 0.03 | [31,42,71] | |||||||
63 | 2-Heptenal | Fresh, fatty, green | 0.35 | 2.16 | [31,35] | ||||||||
64 | Decanal | 1.15 | 0.06 | [31,71] | |||||||||
65 | 2,4-Nonadienal | 0.11 | 0.24 | [31] | |||||||||
66 | Dodecanal | 1.71 | [31] | ||||||||||
67 | 2,4-Decadienal | 0.14 | [31] | ||||||||||
68 | Ketones 3-Hydroxy-2-butanone | Butter, cheese, caramel | 7.58 | 0.001 | [48,52] | ||||||||
69 | 2-Octanone | Earthy, herbal | 0.07 | [35,52] | |||||||||
70 | 2-Nonanone | 0.37, 0.01 | [52,71] | ||||||||||
71 | 2-Decanone | 0.32 | [52] | ||||||||||
72 | Undecanone | 0.05 | 0.18, 0.62 | 0.77 | [52] | ||||||||
73 | 2-Butanone | 1.35, 1.3 | 2.2, 38.2, 53.3 | 1.6, 0.3 | 0.2 | 0.3 | 0.8 | 0.6 | 0.56 | 0.4 | [42,52,65,71] | ||
74 | 3-Octanone | Herbal, lavender, mushroom | 0.20, 4.2 | 1.7, 0.38, 2.6 | 4.6, 0.2 | 7.3 | 4.2 | 5.3 | 8.8 | 0.05, 0.3 | 2.0 | 8.29 | [31,42,48,52,65,71] |
75 | 2-Propanone | 0.09 | 0.57 | [31] | |||||||||
76 | 3-Penten-2-one | 0.44 | [31] | ||||||||||
77 | 5-Methyl-2-heptanone | 0.21 | [31] | ||||||||||
78 | 2,3-Octanedione | 0.06 | 0.06 | [31] | |||||||||
79 | 3-Hydroxy-2-butanone | 0.06 | [31] | ||||||||||
80 | 3-Octen-2-one | 0.37 | 0.015 | [31,71] | |||||||||
81 | 1-Octen-3-one | Mushroom, earthy, musty | 0.03 | 0.70 | [35,42,53] | ||||||||
82 | Aromatic compounds Benzeneacetaldehyde | Honey, sweet, floral | 0.27 | 0.19, 1.85 | 1.10 | 0.11, 0.18 | [31,35,42,52,71] | ||||||
83 | 1-Methoxy-3-methylbenzene | Narcissus | 2.29, 4.2 | 3.7 | 44.50 | 10.60 | 69.5 | 17.4 | 28.3 | 9.05, 0.3 | 37.9 | [31,52,65] | |
84 | Bis(2-Methylpropyl) ester 1,2-Benzenedicarboxylic acid | 1.887 | 0.81 | [52] | |||||||||
85 | Dibutyl phthalate | 0.29 | 0.25 | [52] | |||||||||
86 | Ethylbenzene | 0.66 | [52] | ||||||||||
87 | 1,4-Dimethylbenzene | 7.19, 0.23 | [31,52] | ||||||||||
88 | 1-Ethyl-2-methyl-benzene | 0.24 | [52] | ||||||||||
89 | Phenylethyl alcohol | Floral, yeast, rose | 0.19 | 0.70, 3.82 | 0.002 | [31,48,52] | |||||||
90 | 2,4-Dimethylphenol | 0.93 | [52] | ||||||||||
91 | 1-Methyl-3-(1-methylethyl)benzene | 0.68 | [52] | ||||||||||
92 | Acetophenone | 1.07 | [52] | ||||||||||
93 | Ethylbenzene | 0.33 | [31] | ||||||||||
94 | 1,3-Dimethylbenzene | 0.11 | [31] | ||||||||||
95 | 1,2,4-Trimethylbenzene | 0.07 | 0.20 | [31] | |||||||||
96 | Methoxybenzene | 0.83 | [31] | ||||||||||
97 | 2-(1-Methylethyl)phenol | 0.19 | [31] | ||||||||||
98 | Benzaldehyde | Sweet, bitter, almond | 1.44 | 6.94 | 0.06 | [31,35,71] | |||||||
99 | 4-Hydroxycroman | 0.38 | [31] | ||||||||||
100 | 1,2-Dimethoxybenzene | 2.66 | [31] | ||||||||||
101 | 1,3-Dimethoxybenzene | 0.15 | [31] | ||||||||||
102 | Naphtalene | 0.04 | 0.71 | [31] | |||||||||
103 | 2,5-Dimethoxytoluene | 0.17 | [31] | ||||||||||
104 | 3,4-Dimethoxytoluene | 0.12 | [31] | ||||||||||
105 | 1-Methoxy-4-(1-propenyl)-benzene | 0.04 | [31] | ||||||||||
106 | 2-Methoxy-4-ethyl-6-methylphenol | 0.03 | [31] | ||||||||||
107 | 2,6-Bis(1,1-Dimethylethyl)-4-methylphenol | 0.59 | 3.74 | [31] | |||||||||
108 | p-Cresol | Phenolic/leather | 0.03, 0.02 | [31,35,53] | |||||||||
109 | α-Ethylidene-phenylacetaldehyde | 0.18 | 0.60 | [31] | |||||||||
110 | Phenol | 1.37 | [31] | ||||||||||
111 | 1,2-Dimethoxy-4-(2-propenyl)benzene | 0.16 | [31] | ||||||||||
112 | 1-Methyl-4-(phenylmethyl)benzene | 0.07 | [31] | ||||||||||
113 | p-Methyl anisole | 0.15 | [71] | ||||||||||
114 | m-Anisole | 7.1 | 0.8, 1.4 | 0.80 | 0.20 | 3.40 | 0.70 | [42,65] | |||||
115 | 3-Ethyl-5-methylphenol | Leather | 0.02 | [35,42,53] | |||||||||
116 | 1,4-Dimethoxybenzene | Sweet green hay newly mown hay | 0.10 | 0.10 | 2.70 | 0.90 | 0.70 | 12.10 | 0.10 | 2.80 | [65] | ||
117 | 1,4-Dimethoxy-2-methylbenzene | 0.10 | 1.20 | 1.60 | 7.80 | 0.10 | 1.40 | 0.10 | [65] | ||||
118 | Furans and Furanones 2-Acetyl-5-methylfuran | 0.57, 0.27 | [52,71] | ||||||||||
119 | 2-Pentylfuran | Fruity, green, earthy | 0.07 | 0.35 | 0.05 | [31,35,71] | |||||||
120 | 2,3-Dihydro-4-methylfuran | 0.08 | [31] | ||||||||||
121 | 2-Furancarboxaldehyde | 0.18 | [31] | ||||||||||
122 | 3-Butyldihydro-2(3H)-furanone | 0.14 | [52] | ||||||||||
123 | 2(3H)-Dihydrofuranone | 0.25 | 4.49 | [31] | |||||||||
124 | Alkanes and Alkenes Decane | 0.21 | [52] | ||||||||||
125 | Dodecane | 0.08 | [52] | ||||||||||
126 | 2-Methylbutane | 3.30 | [42] | ||||||||||
127 | Octylcyclopropane | 2.20 | [42] | ||||||||||
128 | Undec-1-ene | 0.10 | 0.40 | 2.90 | 1.80 | 1.80 | [65] | ||||||
129 | Terpenes Camphor | 0.07 | [52] | ||||||||||
130 | Limonene | Citrus, orange, fresh, sweet | 0.16 | [35,71] | |||||||||
131 | p-Cymene | 0.008 | [71] | ||||||||||
132 | 2-Methylisoborneol | Mould, earth | 0.02 | [35,53] | |||||||||
133 | Others 3-Methyl-1H-pirazol | 0.07 | [31] | ||||||||||
134 | 3-Ethyl-4,5-dihydro-1H-pyrazole | 0.13 | [31] | ||||||||||
135 | 2-Methylbutanenitrile | 0.10 | 21.90 | [65] | |||||||||
136 | 2-Nitropentane | 3.90 | [65] | ||||||||||
137 | 2-Bromo-2-methylbutane | 2.30 | [65] |
3. Analytical Methods for the Determination of VOC in Truffles
3.1. Gas Chromatography Methods for the Analysis of VOC in Truffles
3.1.1. Sample Preparation Techniques
Static Headspace Extraction for VOC Extraction in Truffles
Purge-and-Trap VOC Collection Technique
HS-Solid Phase Microextraction (HS-SPME) Technique
Solvent-Assisted Flavor Evaporation (SAFE) Technique
3.1.2. Gas Chromatography (GC) Separation
3.1.3. GC Detecting System in Truffles Analysis
GC-Flame Ionization Detector (GC-FID)
GC-Mass Spectrometry (GC-MS)
Gas Chromatography–Olfactometry (GC–O)
3.2. Analysis of VOC from Truffles Using Proton-Transfer-Reaction Mass Spectrometry (PTR-MS)
3.3. Electronic Nose (EN) Sensing in the VOC Analysis of Truffles
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Sampling | Analyte Separation | Detecting System | Reference | |
---|---|---|---|---|
Gas chromatography-based methods (GC). | 1. Static Headspace (SHS). 2. Dynamic HS (DHS). 3. Purge and Trap (PT). 4. HS-Solid phase microextraction (HS-SPME). 5. Direct solvent extraction coupled with solvent-assisted flavor evaporation (DSE-SAFE). | 1. Monodimensional GC: DB-WAX, HP-5MS. 2. Comprehensive two-dimensional GC (GC × GC). | 1. Flame Ionization Detector (GC-FID) | [49,71] |
2. Mass spectrometry detector (GC-MS): | ||||
- Quadrupole MS (QMS) | [70] | |||
- Ion trap mass MS (IT-MS) | [72] | |||
- High-Resolution Time-of-Flight MS (HR-TOF). | [27] | |||
3. Olfactometry detector (GC-O) | [73,74,75] | |||
Proton-transfer-reaction mass spectrometry (PTR-MS). | Direct injection of VOC from the HS. | Not applicable | 1. High-Resolution Time-of-Flight MS (TOF). 2. QMS | [76,77,78] |
Electronic nose (EN) sensing | SHS, DHS, PT, and HS-SPME | Not applicable | 1. Metal-oxide sensors (MOS). | [79,80] |
2. Quartz microbalance (QMB) sensors. | [51,71] |
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Mustafa, A.M.; Angeloni, S.; Nzekoue, F.K.; Abouelenein, D.; Sagratini, G.; Caprioli, G.; Torregiani, E. An Overview on Truffle Aroma and Main Volatile Compounds. Molecules 2020, 25, 5948. https://doi.org/10.3390/molecules25245948
Mustafa AM, Angeloni S, Nzekoue FK, Abouelenein D, Sagratini G, Caprioli G, Torregiani E. An Overview on Truffle Aroma and Main Volatile Compounds. Molecules. 2020; 25(24):5948. https://doi.org/10.3390/molecules25245948
Chicago/Turabian StyleMustafa, Ahmed M., Simone Angeloni, Franks Kamgang Nzekoue, Doaa Abouelenein, Gianni Sagratini, Giovanni Caprioli, and Elisabetta Torregiani. 2020. "An Overview on Truffle Aroma and Main Volatile Compounds" Molecules 25, no. 24: 5948. https://doi.org/10.3390/molecules25245948