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compounds
Flavor compounds
Flavor molecules constitute a heterogeneous
group of compounds, with straight-chain,
branched-chain, aromatic and heteroaromatic
backbones
bearing diverse chemical groups such as
hydroxyl, carbonyl, carboxyl, ester, lactone,
amine, and thiol functions. More than 700 flavor
chemicals have been identified and catalogued
2
Cinnamaldehyde
http://www.hellochem.com/xz/img/img0/986.gif
Ethyl vanillin
http://www.bmrb.wisc.edu/metabolomi
cs/standards/Ethyl_vanillin/lit/jr_167.p
ng
Chemical
Odor
Diacetyl
Buttery
Isoamyl acetate
Banana
Benzaldehyde
Cinnamic aldehyde
Ethyl propionate
Fruity
Methyl anthranilate
Grape
5
Odor
Ethyl-(E,Z)-2,4decadienoate
Allyl hexanoate
Pear
Pineapple
Ethyl maltol
Ethyl vanillin
Vanilla
Methyl salyicyllate
Wintergreen
Limonene
Orange
6
Alcohols R-OH
Carbonyls RR-CO-R
Acids
CHO
R-COO-R
Esters
Lactones
O
R
CO
R-COOH Phenols
8
Estimated world
consumption of
selected aroma
chemicals in flavor
and fragrance
compositions
CHO
OCH3
OH
10
CO2 + H2O
hn
PRIMARY METABOLISM
Photosynthesis
Glucose
SECONDARY
METABOLISM
Building Blocks
Phenylpropanoids
Flavonoids
Alkaloids
Amino Acids
Proteins
synthesis
enzymes
regulation
Nucleic
Acids
reproduction
RNA DNA
G
L
Y
C
O
L
Y
S
I
S
Carbohydrates
SECONDARY
METABOLISM
Fatty Acids
Lipids
Acetyl CoA
Citric Acid
Cycle
Acetogenins
Terpenes
Steroids
11
Glucose
hn
CH2OH (6 carbons)
O
CH2OH
O
OH
HO
CO2
OH
OH
OH
HO
photosynthesis
CH2OH
O
CH2OH
O
OH
OH
O
OH
O
OH
O
OH
starch
glycolysis
CHO
CH OH
CHO
CH OH
HC OH
CH2OP
CH2OP
erythrose4-phosphate
CH2OH
C O
CH2
C OP
COOH
HO
COOH
shikimic
acid
anthanilic
acid
OH
OH
NH2
phenylpropanes
lysine
ornithine
phenylalanine
tyrosine
tryptophan
alkaloids
phosphoenol
pyruvate (PEP)
H3C C SCoA
oxaloacetate
nicotinic
acid
lipids
fatty acids
(3 carbons)
COOH
polyketides
acetogenins
CH2OP
aspartic
acid
acetylcoenzymeA
(2 carbons)
HO
CH3
mevalonic
acid
citric
acid
cycle
energy (ATP)
+ CO2 + H2O
NH3
glutamic acid
terpenes
steroids
carotenoids
12
15
16
Fruit flavors
are formed during brief ripening period
Vegetable flavors
develop when tissue damage occurs
(Intact vegetable generally contains few
volatiles)
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18
n-hexanal, ethyl butyrate, 1-propyl propionate, 1butyl acetate, trans-2-hexenal, ethyl 2methylbutyrate, 2-methylbutyl acetate, 1-hexanol,
hexen-1-ol, trans-2-hexen-1-ol, hexyl acetate,
Esters; alcohols; aldehydes; ketone; acids; including
hexanal; ethyl 2-methyl butyrate
Banana
Peach
Aliphatic
Acids
Alcohols
Esters
Carbonyls
lactones
Carbohydrate
Pyruvate
Acetyl CoA
Lignins
Amino acid
Shikimic acid
Terpene
Mevalonyl CoA
Terpenes
Sesquiterpenes
Hydrocarbons
Alcohols
Carbonyls
monoterpenes
Cinnamic acid
Methyl-Branched
Alcohols
Acids
Esters
carbonyls
Aromatic
Alcohols
Acids
Esters
carbonyls
20
Carbohydrate-derived flavor molecules, including 4-hydroxy-2,5-dimethyl-3(2H)furanone (furaneol), 2,5-dimethyl-4-methoxy-3(2H)-furanone (methoxyfuraneol), 4hydroxy-5-methyl-3(2H)-furanone (norfuraneol), 2-ethyl-4-hydroxy-5-methyl-3(2H)furanone (homofuraneol), 4-hydroxy-2-methylene-5-methyl-3(2H)- furanone (HMMF)
and 3-hydroxy-2-methyl-4H-pyran-4-on (maltol).
22
2 Pyruvate (3C)
CO2
-O2
-O2
+O2
Ethanol
Lactate
TCA Cycle/
Citric Cycle
Glycolysis
23
Pyruvic acid
CH3COCOOH
Acetic acid
CH3COOH
Acetyl CoA
CH3COSCoA
+ CO2
Malonyl CoA
HOOCCH2COSCoA
Malonic Acid
HOOCCH2COOH
24
26
Biosynthesis of Terpenes
isoprene is derived from acetyl-CoA
27
O
HO
CH2 C SCoA
3 acetylCoA
H3C
HO
C
NADPH
H3C
CH2 C SCoA
O
O
HO
C
H3C
HO
C
CH2 CH2 OH
H2O
H3C
H
CH2 C
O:
: ..
HO
CH2 C SCoA
CH2 CH2 OH
SCoA
CH2 C OH
CH2 C SCoA
NADPH
H3C
CH2 C SCoA
CH2 C H
O
mevalonic acid
28
O
H
..
CH2
CoA
CH3
- CO2
CH3 C
S CoA
CH2
LINEAR
BRANCHED
mevalonic acid
CH3
CH2
HO
CH2
OH
C
CH2
CH2 COOH
TERPENES
C
CH3
CH2
H3C
S CoA
CH2
O
CH2
SCoA
S CoA
CH2
O C
POLYKETIDE CHAINS
SCoA
STEROIDS
ACETOGENINS
29
ADP
AMP
2 ATP
CH2 C OH
O
C
H3C
CH2 CH2 OH
:B-Enz
O
CH2 C
CH2 CH2 O
H
P
mevalonic acid
These five-carbon
intermediates are
responsible for the
formation of all the
terpenes.
CH3
H
CH3
P P O CH2
H+
CH2
P P O CH2
DMAPP
3,3-dimethylallyl
pyrophosphate
CH3
Enz-B:
IPP
isopentenyl
pyrophosphate
30
Classification of Terpenes
31
Apocarotenoid formation
Some of the volatile organic compounds in wine come from the grape's skin, or
exocarp, while others come from the grape's flesh, or mesocarp. Organic acids give
wine its tartness, and sugars give it sweetness. Terpenes provide floral or fruity
flavors. Norisoprenoids impart a honeylike character. Thiols are the sulfur-based
compounds behind complex wine aromas such as guava, passionfruit or grapefruit
but when thiols go wrong, they can make a wine taste "funky."
33
Lipids
metabolic pathway for lipid biosynthesis plays
a significant role in flavor formation.
AAT, alcohol acyl CoA transferase; ADH, alcohol dehydrogenase; AER, alkenal
oxidoreductase; AOC, allene oxide cyclase; AOS, allene oxide synthase; HPL,
hydroperoxide lyase; JMT, jasmonate methyltransferase; LOX, lipoxygenase; OPR, 12oxo-phytodienoic acid reductase; 3Z,2E-EI, 3Z,2E-enal isomerase.
36
37
Palmitoyl-CoA (16:0)
+ Acetyl-CoA
Myristoyl-CoA (14:0)
38
39
Lactones
40
41
42
43
(a) Catabolism of branched-chain amino acids leading to methyl branched flavor compounds, and
(b) postulated biosynthesis of sotolon. Formation of aldehyde (a) from amino acids requires the
removal of both carboxyl and amino groups. The sequence of these removals is not fully known
and could be the opposite to that shown or aldehyde could be formed in one step by aldehyde
synthase
44
45
46
Vegetable Flavors
47
Vegetable flavors
flavor again arises from major metabolic processes e.g. Lipids, CHO & amino acids.
Carbohydrate
Fatty acid
Amino acid
Nonvolatile Precursors
Linoleic, Linolenic acid Thioglucosinolates
Cysteine-sulfoxides
Methyl-methionine
Precursor-splitting Enzymes
Lypoxygenase
Carbonyls
Alcohols
Oxo-acids
Thioglucosidases
Isothiocyanates
Nitriles
S C O
Thiocyanates
C-S-lyases
Polysulides
Alkylthosulfinates
None (Heating)
CH3-S-CH3
49
Genus Allium
Enzymes produce volatiles from derivatives
of cysteine (sulfoxides)
Genus Brassica
Enzymes produce volatiles from glucosinolates
50
Alliaceous vegetables
garlic (Allium sativum L.)
onion (Allium cepa L.)
chive (Allium schoenoprasum L.)
leek (Allium porrum L.)
51
Characteristic flavors
not exist in the bulb before processing
53
54
55
GLUCOSINOLATES
56
thioglucosidase
57
58
59
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