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O
C
O
H
OCH3
O
H
Hydrophobicity
of the aromatic ring
OCH3
OCH3
O
H
Hydrogen bonds
(intra and intermolecular)
O
H
Reactivity
of a carbonyl group
(Maillard Reaction)
O
C
CH3
CH3
O
O
O
H
O
C
CH3
O
O
H
20O C
100
40O C
50O C
Percent Vanillin
80
60
60O C
40
20
80O C
0
0
10
20
30
40
50
Days
0O C, 20O C
100
40O C
40O C
Percent Vanillin
80
50O C
60
60O C
40
20
60O C
80O C
0
0
10
12
14
Time (days)
100
Percent Vanillin
80
60
40
20
30
40
50
60
70
80
Temperature (OC)
vanillin
methanol
290
10
M vanillin
280
270
260
250
10
20
30
40
50
60
Temperature ( O C)
water
vanillin
10
8
270
6
230
4
ml Water
310
190
2
150
10
20
30
40
50
60
70
80
Temperature (OC)
vanillin
340
10
M Vanillin
320
310
4
300
10
20
30
40
50
60
70
methanol (40%)
Temperature (OC)
O
C
H
CH3
O
O
H
HEAT
C H
CH3
O
O
O
H
WATER
CH3
O
C
O
CH3
O
CH3
O
H
O
O
H
11
KOH
NaOH
10
9
8
pH
7
6
5
4
3
1000
2000
3000
4000
5000
6000
10
8
2.6
6
2.2
ml Water
3.0
4
1.8
water
vanillin pH 8.0
vanillin pH 6.5
1.4
10
20
30
40
50
60
70
80
Temperature (OC)
3.4
3.0
6
2.6
ml Water
10
4
water
vanillin pH 2.0
vanillin pH 3.0
2.2
10
20
30
40
50
60
70
Temperature (OC)
A schematic view of water structure showing a tight intermolecular arrangement created by hydrogen bonding of
neighboring water molecules.
Maillard Reaction
Inhibitors
Promoters
Cl Br I
ClO4 SCN
Li+ Na+
Water Structure
Makers
(Kosmotropes)
C=O + H2NR
HO
Carbinolamine
H
C=O + H2NR
HO
H
C
Carbinolamine
Aldose
R + HOH
HO C H
HO C H
HO C H
+ HOH
H C OH
H C OH
H C OH
Schiff's base
H
C
Schiff's base
Amadori Rearrangement
H
C
H
C
HC OH
H
N
C OH
HO C H
H
HC
HO C H
HO C H
Schiff's base
1-amino-2-keto sugar
RNH 3
HOH + H
CsCl
OD 420 nm
0.5
0.4
0.3
0.2
LiCl
0.1
20
40
60
80
100
Summary
Conditions, which increase the water solubility of vanillin
(alkalinity or chaotropic agents) enhance water co-volatility
and chemical reactivity of the compound.