Table 4: Main MS-EI fragments of the identified compounds in Table 2 (odorants in glucuronidase-treated urine) and compilation of their odor
thresholds and CAS numbers.
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
0.000077
0.0060 – 0.016
(Blank et al. 1989)
(R. G. Buttery et al. 1997;
Frequently occurring odorants in solvent extracts of human urine after enzymatic hydrolysis
1
Dimethyl trisulphide
3658-80-8
126, 79
Czerny et al. 2008; Hansen et
al. 1992; C. Milo 1995; C Milo
and Grosch 1996)
2
3
3-(Methylthio)-propanal (Methional)
Butanoic acid
3268-49-3
107-92-6
104, 76
60, 73
0.0010 - 0.00014
0.20 – 1.8
(Blank et al. 1989; I.
(R. Buttery and Ling 1995;
Blank et al. 1992 a; P.
Cerny and Grosch 1993; Czerny
Schieberle and Grosch
et al. 2008; H. Guth and Grosch
1994)
1994; Kerler and Grosch 1996)
0.0010 – 0.0028
204 – 7700
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
(Christlbauer 2006;
(Czerny et al. 2008; Karagul-
Leonardos et al. 1969)
Yuceer et al. 2003; J. A. Pino
and Mesa 2006; P Schieberle
1991; Schnabel et al. 1988)
4
2-/3-Methylbutanoic acid
116-53-0
60, 87
2-methylbutanoic acid
2-methylbutanoic acid
or
0.0069 -0.14
0.32 – 6600
503-74-2
(Christlbauer 2006;
(Czerny et al. 2008; Keith and
Steinhaus 2001)
Powers 1968; Larsen and Poll
1992; T. Pyysalo et al. 1977;
Schnabel et al. 1988)
3-methylbutanoic acid
3-methylbutanoic acid
0.00048 – 0.0042
12 – 1600
(Amoore 1977;
(R. Buttery et al. 1990; Czerny
Christlbauer 2006;
et al. 2008; Ong and Acree
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
Steinhaus 2001)
1999; P Schieberle 1991;
Schnabel et al. 1988)
5
(E)-1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-but-2-en-1-
23696-85-
69, 121, 105,
0.0000028
0.00075 – 10
one ((E)--Damascenone)
7
175, 190
(Blank et al. 1989; I.
(R. G. Buttery et al. 1989;
Blank et al. 1992 a)
Czerny et al. 2008; J. A. Pino
and Mesa 2006; P Schieberle
1991; Semmelroch et al. 1995)
6
(E)-3,7-Dimethylocta-2,6-dien-1-ol (Geraniol)
106-24-1
69, 67, 93, 91,
-
121
1.1 – 75
(Czerny et al. 2008; Ong and
Acree 1999; J. Pino et al. 1986;
T. Pyysalo et al. 1977; Schuh
and Schieberle 2006)
7
2-Methoxyphenol (Guaiacol)
90-05-1
124, 109, 81
0.00028 – 0.0015
0.84 – 21
(H Guth and Grosch
(R. Buttery et al. 1971; Cerny
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
1991; Yang et al. 2008)
and Grosch 1993; Czerny et al.
2008; Kerler and Grosch 1996;
Wassermann 1966)
8
2-Methoxy-5-methylphenol (5-Methylguaiacol)
1195-09-1
138, 123, 95,
-
-
9
3-Hydroxy-2-methylpyran-4-one (Maltol)
118-71-8
126, 71, 97, 127
-
210 – 35000
(R. G. Buttery et al. 1997;
Karagul-Yuceer et al. 2003;
Keith and Powers 1968; Pittet et
al. 1970)
10
4-Ethyl-2-methoxyphenol (4-Ethylguaiacol)
2785-89-9
137, 152
0.000017
4.4 – 50
(I. Blank et al. 1992 a)
(Czerny et al. 2008;
Semmelroch et al. 1995)
11
4-Hydroxy-2,5-dimethyl-3(2H)-furanone (Furaneol)
3658-77-3
128, 57, 85, 129
0.00087 – 0.0010
3.2 – 1700
(I. Blank et al. 1992 a;
(Czerny et al. 2008; Kerler and
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
P. Schieberle and
Grosch 1996; Larsen and Poll
Grosch 1994)
1992; Semmelroch et al. 1995;
Wilson III et al. 1990)
12
-Nonalactone
104-61-0
85, 57
-
9.7 – 27
(Czerny et al. 2008)
13
2-Methoxy-4-methylphenol (4-Methylguaiacol)
93-51-6
138, 123, 95, 67
-
10 - 90
(Czerny et al. 2008; Kennison et
al. 2007; Wassermann 1966)
14
4-Methylphenol (p-Cresol)
106-44-5
107, 108, 77, 79
0.00055 – 0.0010
1.0 - 55
(Blank et al. 1989;
(R. G. Buttery et al. 1988;
Leonardos et al. 1969)
Czerny et al. 2008; Hoak 1957;
Karagul-Yuceer et al. 2003;
Kerscher 2000)
15
-Decalactone
706-14-9
85, 128
-
1.1 – 90
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
(Czerny et al. 2008; Engel et al.
1988; Keith and Powers 1968;
Larsen and Poll 1992; J. A. Pino
and Mesa 2006)
16
-Decalactone
705-86-2
99, 71
-
2.5 - 410
(Czerny et al. 2008; Engel et al.
1988; Karagul-Yuceer et al.
2003; Ong and Acree 1999; J.
A. Pino and Mesa 2006)
17
4-Allyl-2-methoxyphenol (Eugenol)
97-53-0
164, 149
0.00024
0.71 – 150
(Blank et al. 1989)
(I Blank et al. 1992 b; R.
Buttery et al. 1971; Czerny et
al. 2008; J. A. Pino and Mesa
2006; T. Pyysalo et al. 1977)
No.a
18
Odorant
3-Hydroxy-4,5-dimethyl-2(5H)furanone (Sotolone)
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
28664-35-
83, 55, 128, 129
0.000010 – 0.000014
0.30 - 20
(I. Blank et al. 1992 a;
(Czerny et al. 2008; Kerler and
Christlbauer 2006)
Grosch 1996; Semmelroch et al.
9
1995; Zeller and Rychlik 2006)
19
2-Methoxy-4-vinylphenol (4-Vinylguaiacol)
7786-61-0
150, 135, 107, 77
0.00057 – 0.0028
3.0 – 100
(Blank et al. 1989; I.
(R. Buttery and Ling 1995; R.
Blank et al. 1992 a;
G. Buttery et al. 1988; Czerny
Yang et al. 2008)
et al. 2008; J. A. Pino and Mesa
2006; P Schieberle 1991)
20
2-Methoxy-5-vinylphenol (5-Vinylguaiacol)
621-58-9
-
0.15 – 0.35
(Scheidig et al. 2007)
21
-Undecalactone
104-67-6
85, 57
0.00012
2.1 - 410
(Christlbauer 2006)
(Czerny et al. 2008; Greger
2007; Keith and Powers 1968;
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
J. A. Pino and Mesa 2006)
22
Indole
120-72-9
117, 90, 89
0.0081
11 – 140
(Yang et al. 2008)
(R. G. Buttery et al. 1988;
Czerny et al. 2008; KaragulYuceer et al. 2003)
23
2H-Chromen-2-one (Coumarin)
91-64-5
118, 146, 89, 63
-
25 -250
(R. G. Buttery et al. 1978;
Cartwright and Kelley 1952;
Masanetz and Grosch 1998)
24
4-Hydroxy-3-methoxybenzaldehyde (Vanillin)
121-33-5
151, 152, 123, 81
0.00032 - 0.00085
25 – 1200
(Blank et al. 1989; I.
(R. G. Buttery et al. 1997;
Blank et al. 1992 a;
Czerny et al. 2008; Ong and
Christlbauer 2006)
Acree 1999; Schuh and
Schieberle 2006; Semmelroch et
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
al. 1995; Zeller and Rychlik
2007)
25
5-Androst-16-en-3-one (Androstenone)
18339-16-
-
7
26
Androsta-4,16-dien-3-one (Androstadienone)
794-58-9
-
0.0021
0.18
(Amoore 1977)
(Amoore 1977)
-
-
Odorants that were only present in the minority of solvent extracts of human urine after enzymatic hydrolysis
1
2
Butan-2,3-dione (Diacetyl)
Oct-1-en-3-one
431-03-8
4312-99-6
-
-
0.00026 – 0.014
1.0 – 6.5
(Christlbauer 2006; I.
(Czerny et al. 2008; R. G.
Blank et al. 1992 a;
Buttery et al. 1997; R. Buttery
Hall and Andersson
and Ling 1995; C. Milo 1995;
1983)
Mulders 1973)
0.000020 - 0.00010
0.0050 – 4.0
(Christlbauer 2006;
(R. G. Buttery et al. 1978;
Koszinowski and
Czerny et al. 2008; R. G.
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
Piringer 1986)
Buttery et al. 1997; C. Milo
1995; H. Pyysalo and Suihko
1976)
3
2-Acetyl-1-pyrroline
85213-22-
83, 111
5
0.000020 – 0.000028
0.053 - 0.12
(Blank et al. 1989;
(R. G. Buttery et al. 1983; R. G.
Hofmann et al. 1995; P. Buttery et al. 1988; Czerny et
4
Phenol
108-95-2
94, 66, 65
Schieberle and Grosch
al. 2008; R. Buttery and Ling
1991, 1994)
1995)
0.047
31 - 10000
(Leonardos et al. 1969)
(Hoak 1957; Young et al. 1996)
5
-Nonalactone
3301-94-8
71, 99, 114, 128
-
-
6
3-Ethylphenol
620-17-7
107, 122, 77
-
0.85 – 1.7
(Czerny et al. 2008)
7
5-ethyl-3-hydroxy-4-methyl-2(5H)-furanone (Abhexone)
698-10-2
-
0.0000028
7.5 – 500
No.a
Odorant
CAS
MS-EI
Odor threshold in air
Odor threshold in water
numberb
fragmentsc
[µg//L]
(orthonasal) [µg//L]
(I. Blank et al. 1992 a)
(Semmelroch et al. 1995; Pittet
et al. 1970)
8
3-Methylindole (Skatol)
83-34-1
130, 131, 103, 77
0.000020
0.13 – 3.0
(Christlbauer 2006)
(Audouin et al. 2001; R. G.
Buttery et al. 1997; Czerny et
al. 2008; Heiler and Schieberle
1997; Karagul-Yuceer et al.
2003)
9
7-Methoxychromen-2-one (7-Methoxycoumarin)
531-59-9
-
-
Footnotes to Table 4a
a) Numbering refers to Figure 3a and 3b (supplementary material and Table 2.
b) Chemical abstracts service number.
c) Main MS-EI fragments as obtained in our experiments. Fragments are listed according to their relative height.
-
Amoore, J. E. (1977). Specific anosmia and concept of primary odors Chemical Senses & Flavour, 2(3), 267-281.
Audouin, V., Bonnet, F., Vickers, Z., & Reineccius, G. (2001). Limitations in the use of odor activity values to determine important odorants in
foods. In J. Leland, S. P, A. Buettner, & A. TE (Eds.), Gas Chromatography Olfactometry. The State of Art. (pp. 156-171, ACS Symposium
Series, Vol. 782): American Chemical Society.
Blank, I., Fischer, K. H., & Grosch, W. (1989). intensive neutral odorants of linden honey - differences from honeys of other botanical origin.
Zeitschrift Fur Lebensmittel-Untersuchung Und-Forschung, 189(5), 426-433.
Blank, I., Sen, A., & Grosch, W. (1992 a). potent odorants of the roasted powder and brew of arabica coffee Zeitschrift Fur LebensmittelUntersuchung Und-Forschung, 195(3), 239-245.
Blank, I., Sen, A., & Grosch, W. (1992 b). Sensory study on the character-impact flavour compounds of dill herb (Anethum graveolens L.). Food
Chemistry, 43(5), 337-343.
Buttery, R., & Ling, L. (1995). Volatile flavor components of corn tortillas and related products. Journal of Agricultural and Food Chemistry,
43(7), 1878-1882.
Buttery, R., Seifert, R., Guadagni, D., & Ling, L. (1971). Characterization of additional volatile components of tomato. Journal of Agricultural and
Food Chemistry, 19(3), 524-529.
Buttery, R., Teranishi, R., Ling, L., & Turnbaugh, J. (1990). Quantitative and sensory studies on tomato paste volatiles. Journal of Agricultural and
Food Chemistry, 38(1), 336-340.
Buttery, R. G., Ling, L. C., & Bean, M. M. (1978). Coumarin off-odor in wheat-flour Journal of Agricultural and Food Chemistry, 26(1), 179-180.
Buttery, R. G., Ling, L. C., Juliano, B. O., & Turnbaugh, J. G. (1983). cooked rice aroma and 2-acetyl-1-pyrroline. Journal of Agricultural and
Food Chemistry, 31(4), 823-826.
Buttery, R. G., Ling, L. C., & Stern, D. J. (1997). Studies on popcorn aroma and flavor volatiles. Journal of Agricultural and Food Chemistry,
45(3), 837-843.
Buttery, R. G., Teranishi, R., Flath, R. A., & Ling, L. C. (1989). fresh tomato volatiles - composition and sensory studies Acs Symposium Series,
388, 213-222.
Buttery, R. G., Turnbaugh, J. G., & Ling, L. C. (1988). contribution of volatiles to rice aroma. Journal of Agricultural and Food Chemistry, 36(5),
1006-1009.
Cartwright, L. C., & Kelley, P. H. (1952). Flavor quality and strength of propenyl guaethol as a vanilla extender or replacement. Food Technology,
6, 373-376.
Cerny, C., & Grosch, W. (1993). quantification of character-impact odor compounds of roasted beef Zeitschrift Fur Lebensmittel-Untersuchung
Und-Forschung, 196(5), 417-422.
Christlbauer, M. (2006). Evaluation of odours from agricultural sources by methods of molecular sensory. TU Munich, Munich.
Czerny, M., Christlbauer, M., Fischer, A., Granvogl, M., Hammer, M., Hartl, C., et al. (2008). Re-investigation on odour thresholds of key food
aroma compounds and development of an aroma language based on odour qualities of defined aqueous odorant solutions. European Food
Research and Technology, 228(2), 265-273, doi:10.1007/s00217-008-0931-x.
Engel, K. H., Flath, R. A., Buttery, R. G., Mon, T. R., Ramming, D. W., & Teranishi, R. (1988). Investigation of volatile constituents in nectarines.
1. Analytical and sensory characterization of aroma components in some nectarine cultivars Journal of Agricultural and Food Chemistry,
36(3), 549-553.
Greger, V. (2007). Characterisation of key aroma compounds in apricots and peaches with special emphasis on lactones and their formation during
processing. TU Munich, Munich.
Guth, H., & Grosch, W. (1991). A comparative study of the potent odorants of different virgin olive oils. Lipid/Fett, 93(9), 335-339.
Guth, H., & Grosch, W. (1994). identification of the character impact odorants of stewed beef juice by instrumental analyses and sensory studies
Journal of Agricultural and Food Chemistry, 42(12), 2862-2866.
Hall, G., & Andersson, J. (1983). Volatile fat oxidation products. I. Determination of odour thresholds and odour intensity functions by dynamic
olfactometry. Lebensmittel-Wissenschaft und -Technologie, 16, 354-361.
Hansen, M., Buttery, R., Stern, D., Cantwell, M., & Ling, L. (1992). Broccoli storage under low-oxygen atmosphere: identification of higher boiling
volatiles. Journal of Agricultural and Food Chemistry, 40(5), 850-852.
Heiler, C., & Schieberle, P. (1997). Quantitative instrumental and sensory studies on aroma compounds contributing to a metallic flavour defect in
buttermilk. International Dairy Journal, 7(10), 659-666.
Hoak, R. The Cause of Taste and Odor in Drinking Water. In Proceedings of the 11th industrial waste conference, 1957 (Vol. 91, pp. 229) West
Lafayette: Purdue University.
Hofmann, T., Hassner, R., & Schieberle, P. (1995). determination of the chemical structure of the intense roasty, popcorn-like odorant 5-acetyl-2,3dihydro-1,4-thiazine Journal of Agricultural and Food Chemistry, 43(8), 2195-2198.
Karagul-Yuceer, Y., Vlahovich, K. N., Drake, M. A., & Cadwallader, K. R. (2003). Characteristic aroma components of rennet casein. Journal of
Agricultural and Food Chemistry, 51(23), 6797-6801, doi:10.1021/jf0345806.
Keith, E. S., & Powers, J. J. (1968). Determination of Flavor Threshold Levels and Sub Threshold, Additive, and Concentration Effects. Journal of
Food Science, 33(2), 213-218.
Kennison, K., Wilkinson, K., Williams, H., Smith, J., & Gibberd, M. (2007). Smoke-derived taint in wine: Effect of postharvest smoke exposure of
grapes on the chemical composition and sensory characteristics of wine. Journal of Agricultural and Food Chemistry, 55(26), 10897-10901.
Kerler, J., & Grosch, W. (1996). Odorants contributing to warmed-over flavor (WOF) of refrigerated cooked beef. Journal of Food Science, 61(6),
1271-&.
Kerscher, R. (2000). Objektivierung tierartspezifischer Aromaunetrschiede bei erhitztem Fleisch. TU München, Munich.
Koszinowski, J., & Piringer, O. (1986). Evaluation of off-odors in food packaging - the role of conjugated unsaturated carbonyl compounds.
Journal of Plastic Film & Sheeting, 2, 40-50.
Larsen, M., & Poll, L. (1992). Odor thresholds of some important aroma compounds in strawberries Zeitschrift Fur Lebensmittel-Untersuchung
Und-Forschung, 195(2), 120-123.
Leonardos, G., Kendall, D., & Barnard, N. (1969). Odor threshold determinations of 53 odorant chemicals. Journal of the Air Pollution Control
Association, 19(2), 91-95.
Masanetz, C., & Grosch, W. (1998). Hay-like off-flavour of dry parsley. Zeitschrift Fur Lebensmittel-Untersuchung Und-Forschung A-Food
Research and Technology, 206(2), 114-120.
Milo, C. (1995). Odorants of boiled trout, boiled cod and salmon before and after storage of the raw material TU Munich, Munich.
Milo, C., & Grosch, W. (1996). Changes in the odorants of boiled salmon and cod as affected by the storage of the raw material. Journal of
Agricultural and Food Chemistry, 44(8), 2366-2371.
Mulders, J. E. (1973). Quantitative determination of constituents in the vapour and their odour values. .Zeitschrift Fur Lebensmittel-Untersuchung
Und-Forschung, 151, 310-317.
Ong, P. K. C., & Acree, T. E. (1999). Similarities in the aroma chemistry of Gewurztraminer variety wines and lychee (Litchi chinesis Sonn.) fruit.
Journal of Agricultural and Food Chemistry, 47(2), 665-670.
Pino, J., Torricella, R., & Orsi, F. (1986). Correlation between sensory and gas-chromatographic measurements on grapefruit juice volatiles
Nahrung-Food, 30(8), 783-790.
Pino, J. A., & Mesa, J. (2006). Contribution of volatile compounds to mango (Mangifera indica L.) aroma. Flavour and Fragrance Journal, 21(2),
207-213, doi:10.1002/ffj.1703.
Pittet, A., Rittersbacher, P., & Muralidhara, R. (1970). Flavor properties of compounds related to maltol and isomaltol. Journal of Agricultural and
Food Chemistry, 18(5), 929-933.
Pyysalo, H., & Suihko, M. (1976). Odour characterization and threshold values of some compounds in fresh mushrooms. LebensmittelWissenschaft und -Technologie, 9, 371-373.
Pyysalo, T., Suihko, M., & Honkanen, E. (1977). Odour thresholds of the major volatiles identified in cloudberry (Rubus chamaemorus L.) and
arctic bramble (Rubus arcticus L.). Lebensmittel-Wissenschaft und -Technologie, 10, 36–39.
Scheidig, C., Czerny, M., & Schieberle, P. (2007). Changes in key odorants of raw coffee beans during storage under defined conditions. Journal of
Agricultural and Food Chemistry, 55(14), 5768-5775.
Schieberle, P. (1991). Primary odorants of pale lager beer. Zeitschrift für Lebensmittel-Untersuchung und -Forschung A, 193(6), 558-565.
Schieberle, P., & Grosch, W. (1991). potent odorants of the wheat bread crumb - differences to the crust and effect of a longer dough fermentation
Zeitschrift Fur Lebensmittel-Untersuchung Und-Forschung, 192(2), 130-135.
Schieberle, P., & Grosch, W. (1994). potent odorants of rye bread crust - differences from the crumb and from wheat bread crust Zeitschrift Fur
Lebensmittel-Untersuchung Und-Forschung, 198(4), 292-296.
Schnabel, K., Belitz, H., & von Ronson, C. (1988). Investigations on the structure–activity relationships of odorous substances. 1. Detection
thresholds and odour qualities of aliphatic and alicyclic compounds containing functional oxygen. Zeitschrift Fur LebensmittelUntersuchung Und-Forschung, 187, 215–223.
Schuh, C., & Schieberle, P. (2006). Characterization of the key aroma compounds in the beverage prepared from Darjeeling black tea: Quantitative
differences between tea leaves and infusion. Journal of Agricultural and Food Chemistry, 54(3), 916-924, doi:10.1021/jf052495n.
Semmelroch, P., Laskawy, G., Blank, I., & Grosch, W. (1995). Determination of potent odourants in roasted coffee by stable isotope dilution
assays. Flavour and Fragrance Journal, 10(1), 1-7.
Steinhaus, M. (2001). Important odorants in hop (Humulus lupulus L.) TU München, München.
Wassermann, A. E. (1966). Organoleptic evaluation of three phenols present in wood smoke. J. Food Sci., 31, 1005-1010.
Wilson III, C., Shaw, P., & Knight Jr, R. (1990). Importance of some lactones and 2, 5-dimethyl-4-hydroxy-3 (2H)-furanone to mango (Mangifera
indica L.) aroma. Journal of Agricultural and Food Chemistry, 38(7), 1556-1559.
Yang, D., Shewfelt, R., Lee, K., & Kays, S. (2008). Comparison of odor-active compounds from six distinctly different rice flavor types. Journal of
Agricultural and Food Chemistry, 56(8), 2780-2787.
Young, W. F., Horth, H., Crane, R., Ogden, T., & Arnott, M. (1996). Taste and odour threshold concentrations of potential potable water
contaminants. . Water Research., 30(2), 331-340.
Zeller, A., & Rychlik, M. (2006). Character impact odorants of fennel fruits and fennel tea. Journal of Agricultural and Food Chemistry, 54(10),
3686-3692, doi:10.1021/jf052944j.
Zeller, A., & Rychlik, M. (2007). Impact of estragole and other odorants on the flavour of anise and tarragon. Flavour and Fragrance Journal,
22(2), 105-113, doi:10.1002/ffj.1765.