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Table 2 Changes in volatile compounds as a function of cysteine

From: Flavor improving effects of cysteine in xylose–glycine–fish waste protein hydrolysates (FPHs) Maillard reaction system

No.

CAS

Compounds

F

A

B

C

D

E

Odor description

  

Furans

 

179.9 ± 7.21

36.62 ± 2.54

13.39 ± 1.25

15.40 ± 1.03

8.13 ± 0.92

 

1

534–22-5

2-Methylfuran

ND

13.50 ± 1.21a

ND

ND

ND

ND

Chocolate, coffee, nut

2

98–01-1

Furfural-M

ND

121.7 ± 10.2a

32.33 ± 2.8b

9.54 ± 0.83c

10.94 ± 0.24c

3.30 ± 0.12c

Almond

3

1192–62-7

2-Acetylfuran

ND

3.70 ± 0.28b

2.89 ± 0.53d

3.55 ± 0.12c

4.46 ± 0.41a

3.37 ± 0.22c

Almond, nutty, milk,

4

3194–15-8

1-Propanone,1-(2-furanyl)-

ND

2.80 ± 0.11a

0.72 ± 0.31b

0.3 ± 0.05c

ND

ND

Sulfurous

5

13679–41-9

3-Phenylfuran

ND

2.31 ± 0.16a

0.67 ± 0.07b

ND

ND

ND

 

6

19377–82-3

2-Furanmethanamine,N-(2-furanylmethylene)-

ND

35.89 ± 2.42a

ND

ND

ND

ND

 

7

3777–69-3

2-Amylfuran

ND

ND

ND

ND

ND

1.45 ± 0.23a

Grass

  

Sulfur-containing compound

ND

17.34 ± 1.25

25.05 ± 2.46

62.27 ± 5.31

298.50 ± 21.43

190.14 ± 11.34

 

8

624–92-0

Dimethyl disulfide

ND

5.56 ± 0.2a

ND

ND

ND

ND

Sulfurous, vegetable, onion

9

3658–80-8

Dimethyl trisulfide

ND

1.94 ± 0.1a

ND

ND

ND

ND

Sulfurous, cooked onion, meaty

10

3268–49-3

3-(Methylthio) propionaldehyde

ND

8.81 ± 0.67b

12.09 ± 0.7a

4.34 ± 0.13c

1.59 ± 0.04d

1.55 ± 0.03d

Meaty, cooked onion, seafood

11

24295–03-2

2-Acetylthiazole

ND

1.03 ± 0.02b

3.26 ± 0.12b

14.35 ± 0.78a

1.36 ± 0.06ab

1.26 ± 0.05b

Beef, nutty, popcorn, roasted peanuts

12

28588–74-1

2-Methyl-3-furanthiol

ND

ND

4.31 ± 0.25d

18.16 ± 1.23c

43.73 ± 3.52b

55.35 ± 3.87a

Meaty

13

932–95-6

2,5-Thiophenedicarboxaldehyde

ND

ND

3.98 ± 0.14d

16.79 ± 0.98b

32.23 ± 2.81a

14.87 ± 0.84c

 

14

57500–00-2

Methyl furfuryl disulfide

ND

ND

1.41 ± 0.08b

2.21 ± 0.22a

ND

ND

Sulfury, coffee, roasted alliaceous, meaty

15

5834–16-2

3-Methyl-2-thiophene carboxaldehyde

ND

ND

ND

6.16 ± 0.73b

8.67 ± 0.35a

5.52 ± 0.43c

 

16

98–03-3

2-Thenaldehyde

ND

ND

ND

0.26 ± 0.03b

1.14 ± 0.05a

ND

Bitter almonds

17

98–02-2

Furfuryl mercaptan

ND

ND

ND

ND

209.8 ± 12.41a

111.6 ± 8.3b

Sulfury, roasted, coffee, fatty

18

1639–04-9

2-Methyl-3-pentanethiol

ND

ND

ND

ND

1.24 ± 0.15a

ND

 

19

554–14-3

2-Methylthiophene

ND

ND

ND

ND

ND

4.87 ± 0.28a

Sulfurous, alliaceous onion, green

  

Nitrogen-containing compounds

3.1 ± 0.21

1119.0 ± 32.83

351.00 ± 18.76

314.99 ± 23.85

49.14 ± 2.96

40.60 ± 3.98

 

20

290–37-9

Pyrazine

ND

ND

3.93 ± 0.29a

ND

ND

ND

Sweet corn

21

5910–89-4

2,3-Dimethyl pyrazine

ND

0.69 ± 0.16a

ND

ND

ND

ND

Nutty, peanut, coffee, walnut caramel

22

14667–55-1

2,3,5-Trimethyl Pyrazine

ND

47.62 ± 2.17a

ND

ND

ND

ND

Nutty, potato, roasted peanut

23

13360–65-1

3-Ethyl-2,5-dimethyl- Pyrazine

ND

34.22 ± 2.29a

ND

ND

ND

ND

Potato, cocoa, roasted nutty

24

91010–41-2

2-Methyl-6-(3-methyl-butyl)-pyrazine

ND

1.33 ± 0.32a

ND

ND

ND

ND

 

25

56617–70-0

3,5-Dimethyl-2-(2-methylbutyl)- (9CI) pyrazine

ND

10.22 ± 1.37a

ND

ND

ND

ND

 

26

18433–98-2

2,5-Dimethyl-3-(3-methylbutyl)- Pyrazine

ND

104.3 ± 5.6a

21.77 ± 1.86b

ND

ND

ND

Fruity

27

18138–03-9

2-Propylpyrazine

ND

ND

17.51 ± 1.25a

6.85 ± 0.53b

ND

ND

Nutty

28

29460–92-2

2-(2-Methylpropyl)-pyrazine

ND

ND

1.10 ± 0.33b

4.33 ± 0.15a

4.45 ± 0.47a

1.13 ± 0.23b

 

29

13925–07-0

2-Ethyl-3,5-dimethyl- Pyrazine

ND

ND

6.57 ± 0.26a

2.38 ± 0.37b

ND

ND

Almonds, roasted nuts, coffee

30

29461–03-8

2-Methyl-5-propyl-pyrazine

ND

ND

ND

ND

ND

5.46 ± 0.48a

 

31

109–08-0

2-Methyl pyrazine

ND

54.86 ± 3.64c

78.98 ± 5.43b

88.70 ± 9.25a

44.69 ± 3.92d

32.75 ± 2.43e

Nutty, cocoa, chocolate, peanut

32

123–32-0

2,5-Dimethyl pyrazine

3.1 ± 0.43d

851.9 ± 24.32a

216.1 ± 13.52b

202.1 ± 15.26c

ND

ND

Cocoa, roasted nuts, roast beef

33

1438–94-4

1-Furfurylpyrrole

ND

6.99 ± 0.45a

ND

ND

ND

ND

Green, fruity, coffee, vegetable

34

616–43-3

3-Methyl-1H-pyrrole

ND

ND

ND

ND

ND

1.26 ± 0.05a

 

35

274–40-8

Indolizine

ND

ND

5.09 ± 0.67a

3.13 ± 0.26b

ND

ND

 

36

289–95-2

Pyrimidine

ND

6.87 ± 0.53a

ND

7.22 ± 0.83a

ND

ND

 

37

16975–71-6

2-Ethenyl-1-methylimidazole

ND

ND

ND

0.27 ± 0.03a

ND

ND

 

The oxygen-containing compounds

  

Aldehydes

211 ± 14.68

136.43 ± 10.52

218.13 ± 14.89

275.40 ± 21.47

421.63 ± 32.58

280.11 ± 23.24

 

38

110–62-3

Valeraldehyde

1.46 ± 0.45a

ND

ND

ND

ND

ND

 

39

1860–39-5

5-Methylhexanal

3.03 ± 0.24a

ND

ND

ND

2.54 ± 0.12b

ND

 

40

66–25-1

Hexanal

13.56 ± 2.11b

7.60 ± 0.52d

8.44 ± 0.65d

11.83 ± 1.58c

15.44 ± 1.26a

12.55 ± 1.32c

Green, fatty, grass, fruity sweaty

41

111–71-7

Heptaldehyde

8.11 ± 0.65a

4.25 ± 0.34c

5.12 ± 0.59b

5.86 ± 0.42b

8.78 ± 0.64a

7.71 ± 0.84a

Fruity

42

57266–86-1

2-Heptenal, (2Z)-

2.39 ± 0.13a

ND

ND

ND

ND

2.12 ± 0.19a

 

43

100–52-7

Benzaldehyde

32.04 ± 3.42d

27.30 ± 1.42e

69.80 ± 5.23c

108.1 ± 9.75b

138.0 ± 12.3a

70.15 ± 6.75c

Bitter almond, cherry

44

4313–03-5

2,4-Heptadienal, (E,E)-

8.78 ± 0.62a

ND

ND

ND

6.13 ± 0.39b

4.44 ± 0.22c

Fatty, vegetable

45

124–13-0

Octanal

6.56 ± 0.34d

ND

ND

9.76 ± 0.45b

11.36 ± 1.36a

7.96 ± 0.81c

Orange, fatty

46

122–78-1

Benzeneacetaldehyde

5.35 ± 0.67d

13.49 ± 0.95a

12.21 ± 0.78ab

11.26 ± 1.33b

7.12 ± 0.84c

4.94 ± 0.23d

Rose, fruity

47

2548–87-0

(E)-2-Octenal

4.19 ± 0.44 b

ND

ND

ND

ND

6.44 ± 0.73a

Fresh cucumber, fatty, banana

48

124–19-6

Nonanal

48.10 ± 3.56c

24.33 ± 1.76e

37.44 ± 1.75d

51.35 ± 4.58c

96.64 ± 10.41a

75.29 ± 6.54b

Rose, fatty

49

112–31-2

Decanal

10.04 ± 1.24d

6.33 ± 0.34e

10.76 ± 0.89d

14.23 ± 1.25c

18.15 ± 1.64b

23.11 ± 3.21a

fatty, fruit

50

15764–16-6

2,4-Dimethylbenzaldehyde

5.70 ± 0.64a

ND

ND

ND

ND

ND

Bitter almond, sweet

51

2497–25-8

(Z)-2-Decen-1-al

9.32 ± 1.27a

3.37 ± 0.23c

2.64 ± 0.18d

3.64 ± 0.27c

5.71 ± 0.48b

5.37 ± 0.46b

Butter almond

52

28785–06-0

Benzaldehyde, 4-propyl-

19.79 ± 1.65a

13.75 ± 1.54c

16.53 ± 1.48b

ND

ND

ND

 

53

112–44-7

Undecanal

3.92 ± 0.26b

ND

3.34 ± 0.45b

2.54 ± 0.16c

4.57 ± 0.22a

4.41 ± 0.50a

Fruity, rose, flower,

54

25152–84-5

(E,E)-2,4-Decadienal

9.92 ± 1.01a

ND

ND

ND

ND

ND

Cucumber, citrus, nutty

55

2463–77-6

Undecenal

15.72 ± 1.29a

4.33 ± 0.39c

4.84 ± 0.26c

3.53 ± 0.16d

7.15 ± 0.54b

7.02 ± 0.62b

Grass, fatty, citrus

56

112–54-9

Dodecyl aldehyde

3.94 ± 0.08c

ND

ND

2.83 ± 0.13d

5.02 ± 0.39a

4.39 ± 0.23b

Soapy, aldehydic, green floral

57

590–86-3

3-Methylbutyraldehyde

ND

5.27 ± 0.36a

4.15 ± 0.14b

2.99 ± 0.31c

ND

ND

 

58

2548–87-0

(E)-2-Octenal

ND

0.40 ± 0.12d

0.61 ± 0.03c

0.82 ± 0.04b

2.32 ± 0.18a

ND

Meaty, fatty, chicken

59

56599–95-2

2-Bromo octadecanal

ND

3.52 ± 0.21d

10.44 ± 0.92c

4.79 ± 0.26d

17.09 ± 0.95b

44.21 ± 1.58a

 

60

21662–16-8

(E,E)-2,4-Dodecadienal

ND

3.42 ± 0.24b

0.86 ± 0.04c

0.83 ± 0.06c

6.70 ± 0.03a

ND

 

61

638–66-4

Octadecanal

ND

19.08 ± 1.28d

30.96 ± 3.67c

41.04 ± 3.95b

68.95 ± 5.83a

ND

 
  

Alcohols

14.36 ± 1.20

10.02 ± 1.07

6.32 ± 0.52

5.02 ± 0.43

30.63 ± 0.29

19.13 ± 1.12

 

62

89182–08-1

1-Cyclobutene-1-methanol

5.40 ± 0.24a

1.16 ± 0.08c

ND

1.81 ± 0.11b

ND

ND

 

63

4706–89-2

2-Tetradecanol

1.42 ± 0.13a

ND

ND

ND

ND

ND

 

64

2490–48-4

1-Hexadecanol,2-methyl-

7.53 ± 0.34a

3.30 ± 0.24b

2.01 ± 0.12c

1.07 ± 0.08e

3.68 ± 0.26b

1.66 ± 0.09d

 

65

111–28-4

2,4-Hexadien-1-ol

ND

ND

4.31 ± 0.32a

2.14 ± 0.15c

1.96 ± 0.15c

2.53 ± 0.18b

 

66

6261–22-9

2-Pentyn-1-ol

ND

ND

ND

ND

3.61 ± 0.28a

ND

 

67

6712–79-4

Isopinocarveol

ND

ND

ND

ND

8.25 ± 0.69

10.07 ± 1.25

 

68

694–29-1

cis-1-Cyclopentene-3,4-diol

ND

ND

ND

ND

13.12 ± 1.84a

ND

 

69

56554–77-9

13-Heptadecyn-1-ol

ND

ND

ND

ND

ND

4.86 ± 0.35a

 
  

Ketones

ND

16.59 ± 3.04

18.64 ± 2.36

35.59 ± 3.29

61.51 ± 7.35

73.25 ± 5.42

 

70

51004–21-8

2-Butanone,4-cyclopentylidene-

ND

1.50 ± 0.09a

ND

ND

ND

ND

 

71

3796–70-1

Geranylacetone

ND

3.52 ± 0.26d

4.84 ± 0.32c

6.42 ± 0.49b

10.42 ± 1.04a

4.80 ± 0.33c

Grass, rose

72

111–13-7

2-Octanone

ND

1.99 ± 0.12c

2.76 ± 0.26a

2.41 ± 0.22b

2.93 ± 0.03a

2.49 ± 0.10b

Apple, grass, floral

73

116–09-6

Hydroxyacetone

ND

9.59 ± 1.01b

9.80 ± 2.30b

17.79 ± 2.54a

ND

ND

 

74

110–43-0

2-Heptanone

ND

ND

1.24 ± 0.05d

1.56 ± 0.1c

2.45 ± 0.02b

3.48 ± 0.23a

Fruity, coconut, woody

75

13125–74-1

5,9-Dodecadien-1-one,6,10-dimethyl-,(E,E))-

ND

ND

ND

4.68 ± 0.23b

5.24 ± 0.45a

4.38 ± 0.52b

 

76

24653–75-6

2-Propanone,1-mercapto- (8CI,9CI)

ND

ND

ND

2.01 ± 0.28c

10.94 ± 1.95b

14.28 ± 1.65a

 

77

21856–89-3

6-Hydroxyhexan-2-one

ND

ND

ND

0.73 ± 0.02a

ND

ND

 

78

67–64-1

Acetone

ND

ND

ND

ND

29.53 ± 3.01b

36.35 ± 3.57a

Apple, pear

79

107–87-9

2-Pentanone

ND

ND

ND

ND

ND

7.48 ± 0.44a

Fruity

  

Esters

2.72 ± 0.14

2.84 ± 0.16

ND

ND

ND

4.46 ± 0.25

 

80

623–42-7

Methyl butyrate

2.72 ± 0.14b

1.47 ± 0.05b

ND

ND

ND

4.46 ± 0.25a

Fruity, apple, banana

81

5331–43-1

Carbobenzoxyhydrazide

ND

1.37 ± 0.07a

ND

ND

ND

ND

 
  

Acids

ND

33.25 ± 4.23

55.38 ± 4.68

30.72 ± 3.28

39.28 ± 2.37

1.05 ± 0.01

 

82

64–19-7

Acetic acid glacial

ND

33.25 ± 4.23a

22.74 ± 2.36b

18.73 ± 2.1c

ND

ND

Sharp pungent sour vinegar

83

57–10-3

Palmitic acid

ND

ND

32.64 ± 2.84b

12.00 ± 0.87c

39.28 ± 3.16a

ND

 

84

2091–29-4

9-Hexadecenoic acid

ND

ND

ND

ND

ND

1.05 ± 0.09a

 
  

Phenol

25.76 ± 1.63

7.06 ± 0.64

9.93 ± 0.88

8.72 ± 0.24

18.77 ± 0.85

18.78 ± 1.21

 

85

6712–79-4

Isopinocarveol

1.71 ± 0.12a

ND

ND

ND

ND

ND

 

86

96–76-4

2,4-Di-tert-butylphenol

3.98 ± 0.43d

7.06 ± 0.82b

5.90 ± 0.66c

4.72 ± 0.13d

13.67 ± 0.22a

14.17 ± 0.11a

 

87

128–37-0

Butylated hydroxytoluene

20.07 ± 2.24a

ND

4.03 ± 0.29b

4.00 ± 0.16b

ND

ND

 

88

497–39-2

4,6-Di-tert-butyl-m-cresol

ND

ND

ND

ND

3.45 ± 0.42b

4.60 ± 0.53a

 
  1. F: samples without cysteine addition and heating, A: Maillard reaction products without cysteine addition, B: Maillard reaction products with 0.25% cysteine addition, C: Maillard reaction products with 0.5% cysteine addition, D: Maillard reaction products with 0.75% cysteine addition, E: Maillard reaction products with 1.0% cysteine addition
  2. ND not detected
  3. Results are mean ± standard deviation (n = 3). Values with different superscript lowercase letters in the same column mean differ significantly (p < 0.05)