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 numberb / MS-EI fragmentsc / Odor threshold in air [µg//L] / Odor threshold in water (orthonasal) [µg//L] /Frequently occurring odorants in solvent extracts of human urine after enzymatic hydrolysis
1 / Dimethyl trisulphide / 3658-80-8 / 126, 79 / 0.000077
(Blank et al. 1989) / 0.0060 – 0.016
(R. G. Buttery et al. 1997; Czerny et al. 2008; Hansen et al. 1992; C. Milo 1995; C Milo and Grosch 1996)
2 / 3-(Methylthio)-propanal (Methional) / 3268-49-3 / 104, 76 / 0.0010 - 0.00014
(Blank et al. 1989; I. Blank et al. 1992 a; P. Schieberle and Grosch 1994) / 0.20 – 1.8
(R. Buttery and Ling 1995; Cerny and Grosch 1993; Czerny et al. 2008; H. Guth and Grosch 1994; Kerler and Grosch 1996)
3 / Butanoic acid / 107-92-6 / 60, 73 / 0.0010 – 0.0028
(Christlbauer 2006; Leonardos et al. 1969) / 204 – 7700
(Czerny et al. 2008; Karagul-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
or
503-74-2 / 60, 87 / 2-methylbutanoic acid
0.0069 -0.14
(Christlbauer 2006; Steinhaus 2001) / 2-methylbutanoic acid
0.32 – 6600
(Czerny et al. 2008; Keith and Powers 1968; Larsen and Poll 1992; T. Pyysalo et al. 1977; Schnabel et al. 1988)
3-methylbutanoic acid
0.00048 – 0.0042
(Amoore 1977; Christlbauer 2006; Steinhaus 2001) / 3-methylbutanoic acid
12 – 1600
(R. Buttery et al. 1990; Czerny et al. 2008; Ong and Acree 1999; P Schieberle 1991; Schnabel et al. 1988)
5 / (E)-1-(2,6,6-Trimethyl-1,3-cyclohexadienyl)-but-2-en-1-one ((E)-b-Damascenone) / 23696-85-7 / 69, 121, 105, 175, 190 / 0.0000028
(Blank et al. 1989; I. Blank et al. 1992 a) / 0.00075 – 10
(R. G. Buttery et al. 1989; 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
(H Guth and Grosch 1991; Yang et al. 2008) / 0.84 – 21
(R. Buttery et al. 1971; Cerny 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
(I. Blank et al. 1992 a) / 4.4 – 50
(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
(I. Blank et al. 1992 a; P. Schieberle and Grosch 1994) / 3.2 – 1700
(Czerny et al. 2008; Kerler and Grosch 1996; Larsen and Poll 1992; Semmelroch et al. 1995; Wilson III et al. 1990)
12 / g-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 (Blank et al. 1989; Leonardos et al. 1969) / 1.0 - 55
(R. G. Buttery et al. 1988; Czerny et al. 2008; Hoak 1957; Karagul-Yuceer et al. 2003; Kerscher 2000)
15 / g-Decalactone / 706-14-9 / 85, 128 / - / 1.1 – 90
(Czerny et al. 2008; Engel et al. 1988; Keith and Powers 1968; Larsen and Poll 1992; J. A. Pino and Mesa 2006)
16 / d-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
(Blank et al. 1989) / 0.71 – 150
(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)
18 / 3-Hydroxy-4,5-dimethyl-2(5H)furanone (Sotolone) / 28664-35-9 / 83, 55, 128, 129 / 0.000010 – 0.000014 (I. Blank et al. 1992 a; Christlbauer 2006) / 0.30 - 20
(Czerny et al. 2008; Kerler and Grosch 1996; Semmelroch et al. 1995; Zeller and Rychlik 2006)
19 / 2-Methoxy-4-vinylphenol (4-Vinylguaiacol) / 7786-61-0 / 150, 135, 107, 77 / 0.00057 – 0.0028
(Blank et al. 1989; I. Blank et al. 1992 a; Yang et al. 2008) / 3.0 – 100
(R. Buttery and Ling 1995; R. G. Buttery et al. 1988; Czerny 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 / g-Undecalactone / 104-67-6 / 85, 57 / 0.00012
(Christlbauer 2006) / 2.1 - 410
(Czerny et al. 2008; Greger 2007; Keith and Powers 1968; J. A. Pino and Mesa 2006)
22 / Indole / 120-72-9 / 117, 90, 89 / 0.0081
(Yang et al. 2008) / 11 – 140
(R. G. Buttery et al. 1988; Czerny et al. 2008; Karagul-Yuceer 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
(Blank et al. 1989; I. Blank et al. 1992 a; Christlbauer 2006) / 25 – 1200
(R. G. Buttery et al. 1997; Czerny et al. 2008; Ong and Acree 1999; Schuh and Schieberle 2006; Semmelroch et al. 1995; Zeller and Rychlik 2007)
25 / 5a-Androst-16-en-3-one (Androstenone) / 18339-16-7 / - / 0.0021
(Amoore 1977) / 0.18
(Amoore 1977)
26 / Androsta-4,16-dien-3-one (Androstadienone) / 794-58-9 / - / - / -
Odorants that were only present in the minority of solvent extracts of human urine after enzymatic hydrolysis
1 / Butan-2,3-dione (Diacetyl) / 431-03-8 / - / 0.00026 – 0.014
(Christlbauer 2006; I. Blank et al. 1992 a; Hall and Andersson 1983) / 1.0 – 6.5
(Czerny et al. 2008; R. G. Buttery et al. 1997; R. Buttery and Ling 1995; C. Milo 1995; Mulders 1973)
2 / Oct-1-en-3-one / 4312-99-6 / - / 0.000020 - 0.00010
(Christlbauer 2006; Koszinowski and Piringer 1986) / 0.0050 – 4.0
(R. G. Buttery et al. 1978; Czerny et al. 2008; R. G. Buttery et al. 1997; C. Milo 1995; H. Pyysalo and Suihko 1976)
3 / 2-Acetyl-1-pyrroline / 85213-22-5 / 83, 111 / 0.000020 – 0.000028
(Blank et al. 1989; Hofmann et al. 1995; P. Schieberle and Grosch 1991, 1994) / 0.053 - 0.12
(R. G. Buttery et al. 1983; R. G. Buttery et al. 1988; Czerny et al. 2008; R. Buttery and Ling 1995)
4 / Phenol / 108-95-2 / 94, 66, 65 / 0.047
(Leonardos et al. 1969) / 31 - 10000
(Hoak 1957; Young et al. 1996)
5 / d-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
(I. Blank et al. 1992 a) / 7.5 – 500
(Semmelroch et al. 1995; Pittet et al. 1970)
8 / 3-Methylindole (Skatol) / 83-34-1 / 130, 131, 103, 77 / 0.000020
(Christlbauer 2006) / 0.13 – 3.0
(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.
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