link.springer.com · web viewkoszinowski, j., & piringer, o. (1986). evaluation of off-odors in...

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 204 – 7700

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



(Christlbauer 2006;

Leonardos et al. 1969) (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)


0.00048 – 0.0042

(Amoore 1977;

Christlbauer 2006;


12 – 1600

(R. Buttery et al. 1990; Czerny

et al. 2008; Ong and Acree

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[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-

one ((E)--Damascenone)

23696-85-

7

69, 121, 105,

175, 190

0.0000028


Blank et al. 1992 a)

0.00075 – 10


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.

0.84 – 21

(R. Buttery et al. 1971; Cerny

and Grosch 1993; Czerny et al.

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



2008) 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


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;

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



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

(Blank et al. 1989;

Leonardos et al. 1969)

1.0 - 55


Czerny et al. 2008; Hoak 1957;

Karagul-Yuceer et al. 2003;

Kerscher 2000)

15 -Decalactone 706-14-9 85, 128 - 1.1 – 90

(Czerny et al. 2008; Engel et al.

1988; Keith and Powers 1968;

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



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

(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;

0.30 - 20

(Czerny et al. 2008; Kerler and

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



Christlbauer 2006) 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. 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 -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 11 – 140

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



(Yang et al. 2008)


Czerny et al. 2008; Karagul-

Yuceer et al. 2003)

23 2H-Chromen-2-one (Coumarin) 91-64-5 118, 146, 89, 63 - 25 -250


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



Christlbauer 2006)

25 – 1200


Czerny et al. 2008; Ong and

Acree 1999; Schuh and

Schieberle 2006; Semmelroch

et al. 1995; Zeller and Rychlik

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



2007)

25 5-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.


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


Czerny et al. 2008; R. G.

Buttery et al. 1997; C. Milo

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



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 -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

No.a Odorant CAS

numberb

MS-EI

fragmentsc


[µg//L]



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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