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Carbohydrate General
 Source of energy and sweetness:
C6H12O6 + 6 O2 6CO2 + 6H2O + ENERGY
C6H12O6 + 6 O2 6CO2 + 6H2O + SUNLIGHT
 Carbohydrates consists of single units known as
monosaccharidesof multiple units thereof.

Food Chemistry Course  Simple sugars (mono- & disaccharides)

 Oligo- &polisaccharides (sugar polymers)

Simple Sugars monosaccharides

 Glucose
- also known as grape sugar, corn sugar (dextrose)  General formula (CH2O)n
- dextrorotatory (+)  Polyhydroxycarbonyl
- made commercially by hydrolizing starch compounds, e.g. aldoses
(aldehyde based) and ketoses
(ketone based)
 Fructose
 Carbon content can vary
- also known as fruit sugar or laevulose (typically 3-8) for each type of
- laevorotatory (-) saccharide, e.g. pentoses (C5)
- made by hydrolizing starch or isomeri- and hexoses (C6)

zing the glucose from the corn syrup

Sucrose and Lactose:

disaccharides
 Sucrose
– Also known as cane/beet sugar
– Obtained commercially from sugar beet/cane
– Only one isomer present in solution
– Easily crystallized

• Lactose
– Also known as milk sugar
– Primary sugar in mammalian milk (human>cow)
– Also is a by-product of cheese manufacture Lactose consists of a
D-galactose& a D-
– Not very sweet (relative intensity ≤0.3 cf glucose bonded by β-
sucrose) 1-4 glycosidic linkage.
– Hydrolyzed by enzyme β-galactosidase Formula: C12H22O11

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Invert sugar
 Invert sugar is produced by acid hydrolysis of sucrose Fructo-oligosaccharides (FOS), which are found
 Produces a mixture of glucose and fructose in many vegetables, consist of short chains of
fructose molecules.
H2O + sucrose →glucose + fructose
Galactooligosaccharides (GOS), which also
[α]D +66.5º +52.7 º -92.4º
occur naturally, consist of short chains of
–Rotation of solution goes from dextrorotatory to galactose molecules.
laevorotatory overall
These two compounds can be only partially
–Process is called “inversion” of sucrose - digested by humans  they can act as
producing “invert sugar” prebiotics.

Tri-and tetrasaccharides Polysaccharides

Raffinose (Trisaccharide)
 Digestible
α-D-galactopyranosyl-(16)-α-D-glucopyranosyl-(2)- β-D-
fructofuranose – Starches (glycogen/amylose/amylopectin)

Stachyose (Tetrasaccharide)
α-D-galactopyranosyl-(16)-α-D-galactopyranosyl- (1 6)-α-
 Indigestible (dietary fibre/roughage)
D-glucopyranosyl-(12)-β-D-fructofuranose – Cellulose
• Both found in legumes (peas, beans, soya)
– Pectin
• But neither hydrolysed nor digested by humans……
– Seaweed polysaccharides (agarose/carageenan)
• Their presence are providing “a feast” for bacteria (e.g. E. coli)
in the gut which produce H2 and CO2 causing flatulence. – Xanthan and gellan (gums)

glycogen CELLULOSE
 Cellulose is a a linear glucan with β-(1,4)-glycosidic
 Glycogen is the major linkages
carbohydrate storage
molecule in animals. – Humans lack cellulase enzymes, so cellulose is
indigestible for us
 It is a homopolymer of
glucose (a glucan) with α-  Different stereochemistry of glycosidic bond compared to
(1,4)-linkages. starches [i.e. β−(1,4)-vs.α-(1,4)-]
 It is also highly branched, – results in very different molecular shape in solution
with α-(1,6) branch linkages
occurring every 8-10
residues.

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Starches: amylose and

amylopectin
 Starch is the major form of stored carbohydrate in plant cells
e.g. grains, potatoes etc.
 Unbranched starch is called amylose and branched
starch is called amylopectin.
– Amylose: linear glucan with α-(1,4)-glycosidic linkages and
~104 subunits
– Amylopectin: branched glucan with α−(1,4) and α-(1,6)
linkages with ~106 subunits: more compact than amylose for
same MW. Its structure is identical to glycogen, except for a
much lower degree of branching (about every 20-30
residues).

Pectin Other food polysaccharides

 A family of complex polysaccharides that contain
1,4-linked α-D-galactosyluronic acid residues

– can contain up to 20% neutral sugars

– found naturally in fruits, vegetables

– charged at higher pH

– can form GELS

Physical properties
Optical Rotation
Hygroscopicity and Solubility
Ability of certain
# The moisture uptake of sugars in crystallized form is compounds (mostly
variable and depends, fie. on the sugar structure, those with a chiral
isomers present and sugar purity. carbon) to rotate the
plane of polarized
# Solubility decreases as the sugars cake together, as light.
often happens in sugar powders or granulates.
(+) clockwise
# On the other hand, the retention of food moisture by
( - ) anticlockwise
concentrated sugar solutions, e.g., glucose syrup, is
utilized in the baking industry.

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Sensory Properties
Mutarotation  Mono- and oligosaccharides and their corresponding
sugar alcohols, with a few exceptions, are sweet.
Mutarotation is
– a dynamic equilibrium  β-D-Mannose has a sweet-bitter taste, and some
– all isomers can potentially exist in solution oligosaccharides are bitter, e. g. gentiobiose.
– energy/stability of different forms
 The sugars differ in quality of sweetness and taste
Single molecule in solution can interchange intensity. Saccharose is distinguished from other
between sugars by its pleasant taste even at high
– straight chain and ring concentrations. The taste intensity of
– different ring sizes oligosaccharides drops regularly as the chain length
– αandβanomer increases.

 Saccharose is the reference substance usually

chosen as the sweetness reference. The
recognition threshold values for saccharose cited in
the literature vary from 001 to 0037 mol/L
 Taste quality and intensity are dependent not only
on a compound’s structure but on other taste
reception parameters: temperature, pH and the
presence of additional sweet or non-sweet
compounds.

chemical REACTIONs
Fructose vs sucrose & derivatives
 Fructose is sweeter than table sugar 1. Reduction to Sugar Alcohols
(sucrose). The α - &β- furanose forms
(5-ring) are in equilibrium with the Monosaccharides can be reduced
pyranose (6-ring) forms to the corresponding alcohols by
NaBH4 , electrolytically or via
 At higher temperatures (tea and coffee, catalytic hydrogenation.
(D-glucitol)
baking etc.) the equilibrium reaction The alcohol name is derived from
speeds up as the temperature the sugar name in each case by
increases more pyranose (6-ring) replacing the suffix-oseor -
forms its sweetness was reduced & ulosewith the suffix-itol. 
may not help to reduce caloric intake.
D-mannose D-mannitol

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The Maillard Reaction

The Maillard reaction occurs in three main steps:

 Hydrolysis
1. Initial step: formation N glycoside
# a chemical reaction in which a molecule breaks down by
the addition of water.
# Many factors affecting hydrolysis
# Hydrolysis of sucrose yields glucose & fructose about 85%, 1. The immonium ion is formed and then isomerized, this
the reaction temperature can be maintained at 50-60 °C. reaction is called Amadori rearrangement and forms a
compound called ketosamine:

3. The ketosamine products then either dehydrates into

reductones and dehydroreductones, which are caramel, or
products short chain hydrolytic fission products such as
diacetyl, acetol or pyruvaldehyde which then undergo the
Strecker degradation.