Sweeteners

Prepared by Sofia for food chemistry II class meeting #6-7

 Sweeteners in general
• Definition:
• food additives that used either to impart a sweet taste to food or as a
tabletop sweetener (any permitted sweeteners that normally use as
an sugar alternative)
• Sugar and honey are not additives and excluded from official regulation
• Classification:
• High intensity: has a sweet taste, non caloric, no bulk to food, greater
sweetness than sugar and use in very low levels.
• Bulk: generally carbohydrates, providing calories, bulk to food, have
similar sweetness to sugar
 Why do sweeteners taste sweet?
The AH/B theory:
• The saporous (sweet-taste eliciting) is combination between a covalently bound H-bounding
proton (oxygen, nitrogen, chlorine atoms) and an electronegative orbital positioned at about 3
Ao distance
•

• Check this article: http://jn.nutrition.org/content/early/2012/05/02/jn.111.149567.full.pdf

• Check this video: https://www.youtube.com/watch?v=FaBFyEa8-eI

Relative sweetness of various sugars to sucrose
Sugar/sugar Relative Sugar/sugar Relative
alcohol sweetness alcohol sweetness
Fructose 1.70 isomalt 0.45-0.65
Invert sugar 1.30 Erythritol 0.70
Xylitol 0.85-1.20 High fructose corn 1.00
Sucrose 1.00 syrup 55%
Glucose 0.75 Cyclamate 30
Maltitol 0.50-0.90 Aspartame 180
Sorbitol 0.50 Lo han guo extract 180
Mannitol 0.40 Acesulfame K 200
Lactitol 0.30-0.40 Saccharin 300-500
Maltose 0.30 Steviol glycosides 300
Galactose 0.30 Sucralose 600
Lactose 0.15 Neotame 8000
Natural ‘sweeteners’
Chemistry and functional properties of sugars (mono-, di-, and
polysaccharides) and honey
Browning or Maillard reaction

• Reaction between aldehydes and ketones (glucose, galactose, maltose, lactose and
fructose) with amino compounds = Maillard reaction
• The change of polyhydroxycarbonyl compounds when they are heated to high
temperature

are sometimes:
• Desirable: dark color and characteristic odor ( baked odor)
• Undesirable: loss of nutrients, reduction of food protein value, formation of toxic products
(Acrylamide, Furan, Heterocyclic amines, 3-MPCD (Mono Chloro Propan Diol), and 3-
Methyl Imidazolone)
 Sugars-monosaccharides

• Xylose, D-glucose, D-galactose, D-mannose, and D-fructose

• Physical properties: D-xylose
 solid substances,
 soluble in water, less soluble in methanol, ethanol, insoluble in
lipophilic solvent.
 sometimes difficult to crystallize (form supersaturated syrup
solutions),
 many of them have a sweet taste, tasteless or bitter
 Disaccharides
• Sucrose;
• Lactose
• occurs in all plants, commercially obtained from sugar
cane (Saccharum officinarum) and sugar beet (Beta • Sugar in the milk of mammals
vulgaris)
• Soluble in water, and the solubility increases with • Commercial lactose is produced from whey; crystal
increasing temperature lactose is very low hygroscopicity and used in icing
sugar blends
• Caramelized at >200oC; used in soft drinks, baked goods, • It is low sweetness and low solubility, limited
candies, colorant and flavors application (undesirable in condensed milk/ ice
cream)
• Non-redusing sugar
• Lactose, a reducing sugar, can undergo maillard
• Maltase ; reaction resulting (off) flavor compounds and
browning
• It has a characteristic flavor of malt • Lactose is enzymatically hydrolyzed in the small
intestine by β-galactosidase.
• Major end product of enzymatic degradation of starch
by maltase • Inadequate β-galactosidase causes lactose
intolerance; lactose enters to the large intestine,
draws water and causing diarrhea. Lactose is
• It is readily yeast-fermentable sugar, is easily soluble metabolized by bacteria producing gas and
in water and slightly soluble in ethanol’ causing cramps and flatulence
 (Sugar) Syrups

• Some common liquids sweeteners:

• Maple syrup= collected from sap maple tree, concentrated into a syrup

• Golden syrup: evaporated cane juice

• Sorghum syrup: processed from sorghum stalks

• Malt syrup: produced by mashing barley, converting to sugar and

concentrating to the thick syrup

• Corn syrup: differ in glucose concentration (20-98%)

 Starch syrup

• Starch syrups are prepared by partial hydrolysis of starch and producing a mixture of glucose, maltose, and longer chains of
glucose units. Available commercially as soft syrups (extensive hydrolysis) and hard syrups differentiated by DE (dextrose
equivalent, % of reducing sugar in total starch product)

• Syrup with higher DE = sweeter and have greater humectant properties than low DE

• used to impart sweet taste in foods, they don’t crystal easily, they retard sucrose crystallization and act as softening agen ts
 Honey

Honey is sold as either pure honey or honey products; it exists in various forms:
liquid,
crystallized/ granulated: its part of the sugar glucose has been crystallized by losing
water and becoming glucose monohydrate.
creamed/ whipped honey: a supersaturated solution made by controlling the
crystallization process to produce fine crystals, resulting in a smooth and spreadable
products
Some of honey products are:
Dried honey: dehydrated by heating honey mixed with starches/ sugars
Flavored/ fruit honey; added by fruits, color, or flavors
Infused honey: herbs/ peels are added by steeping
 Grading of honey
Grading based on: water content, aroma, flavor,
clarity and absence of defects.

Honey with low moisture; suitable for long preservation

 Physic-chemical properties of honey

• Honey is complex of natural sugars, enzymes, minerals, vitamins, and amino acids

• Honey contains 82.4% carbohydrates (81.1% are sugars)

• Main sugars in honey: fructose (38.5%), glucose (31.0%), sucrose (1.5%0, maltose (7.2%) and
other carbohydrates (4.2% isomaltose, erlose, panose, cellobiose, dextrin, raffinose,
isomaltotriose, isomaltopentaose, maltulose, trehalose, isomaltotriose, isopanose, and formic).

• Sweetness is determined by fructose and glucose

• The color and flavor depends on the nectar and secretions of plants

• A-light colored and low water content honey only slightly change in viscosity at higher
temperatures, but viscosity of dark-colored honey changes at all levels heating temperatures
 Properties and applications

Honey has organic acids (0.6%) and amino acids (0.05%); pH range
(3.5-6.0)
Honey contains enzymes: diastase (amylase), invertase (α-
glucosidase), and glucose oxidase
Honey can increase the sweet perception, decrease sourness,
bitterness intensity and saltiness perception
Crystallization doesn’t effect the nutritional aspects of honey
Applications: bread, beverages, frozen dessert, fruit gels, spreads,
snacks and cereals etc
Nutraceutical aspects of honey

• Excessive heat (37-50oC) causes the loss of important

antibacterial, nutritional, and enzymatic components.
• Honey has low pH (3.2-4.5) that can prevent the growth
microbes
• Honey can play as antiseptic agent when applied to wound
by releasing hydrogen peroxide by enzyme glucose oxidase
 Sugar alcohols (Polyols)
• Naturally present in fruits and vegetables contributing to sweetness or

• Hydrogenated from carbohydrates, which carbonyl group (aldehyde/ketone) is reduced to a

primary/ secondary hydroxyl group

• General formulation ; H(HCHO) n+1H

Comparison of sucrose with sugar alcohols

Sugar/polyol Sweetness (%) GI Cal/g Cooling effect Hygroscopicity

Sucrose 100 60 4 None Medium
Xylitol 100 13 2.5 Very cool High
Maltitol syrup 75 53 3 -
Maltitol 75 36 2.7 None Medium
Erythritol 70 0 0.2 Cool Medium
Sorbitol 60 9 2.5 Cool Very low
Mannitol 60 0 1.5 Cool Low
Isomalt 55 9 2.1 None Low
Lactitol 35 6 2 Slightly cool Medium
Polyglycitol 33 39 2.8 - -

GI = Glycemic Index
 Polyol properties

• Cooling sensation in the oral cavity is caused by the polyols with higher positive
enthalpy of solution

• The melting point ranges from 92oC for xylitol and sorbitol to 165oC for mannitol; polyol
with lower melting produce smooth surface tablets

• Because sugar alcohol lack a carbonyl group, their sweetness differs from carbohydrates

• No maillard and strecker degradation occur

• Mono and disaccharide alcohols are more resistant to enzyme, acids, alkalis, and
heat than sugar/ glucose syrup

• Are suitable for production of non-cariogenic and reduced –calorie products.

Noncariogenicity xylitol ≤ isomalt < sorbitol, maltitol < mannitol≈ lactitol
 Benefits of polyols
• Taste like sugar
• Have low energy
value
• Low
cariogenicity, low
glycemia, low
insulinemia
• Resistant to
fermentation and
acidogenesis by
the dental
plaque
microorganisms
• It is absorbed
slower in
digestive tract
than sucrose
Low Calorie
Nonnutritive
Sweeteners
• = non-nutritive sweeteners
• Classified as:
 synthetic artificial: acesulfame, alitame, aspartame,
cyclamate, neotame, saccharin, and sucralose
 Semisynthetic: neoheperidin dihydrochalcone (NHDC)
 Natural: stevioside, traumatin, and glycyrrhizin
• Offer consumers to enjoy the taste of sweetness with very low or
no energy intake
• Do not provide growth of oral cavity microorganism
• Ingredients of food and beverages market for: obesity treatment,
maintenance of body weight, management of diabetes, prevention
High
and reduction of dental caries intensity
sweeteners
 Characteristics
• Acesulfame-K and saccharin are not metabolized and excreted unchanged by the kidney

• Sucralose, stevioside and cyclamate undergo degrees of metabolism, and the metabolites are readily excreted
 Characteri
• SCF= Scientific food committee of the European community
stics
 Aspartame

• A dipeptide • EFSA (2009)

found no
• 200 x sweeter than sugar indications of
genotoxic nor
• 1 g aspartame provides 4 calories carcinogenic
• White crystalline powder, stable in dry form, but can undergo potential of
degradation depend on pH (degraded at pH <3 and changed at pH ASP.
>6) and temperature (sot good for baking) • But it cannot
• Broken down to its components (aspartic acid, phenylalanine and used by those
methanol) in the gastrointestinal tract suffering from
phenylketonuri
a (PKU)
 Cyclamate

• 35 x sweeter than sugar

• Widely used in low-calorie foods and beverages

• Approved for use in more than 50 countries worldwide (but it is banned in

the USA)

• ADI 11mg/kg body weight (JECFA) and 7 mg/kg body weight (SCF)

• Generally used in sodium salt because it is more soluble than acid form

• It is sweetener, but it can cause gelation and precipitation

• Good stability in soft drink formulation within pH range 2-10

 Saccharin

• Commercially available in 3 forms: acid-, sodium- and calcium saccharin

• The most commonly used: sodium saccharine due its high solubility and stability

• Good stability in solid form and in soft drink

• But, at low pH slowly hydrolyze to 2-sulfobenzoic acid and 2-sulfamoylbenzoic acid

• Applications: used om low-calorie food (for maintain body weight), medically suggested for diabetics

• 300-500 x sweeter than sugar

• High solubility, but has bitter metallic aftertaste

• It is stable at heat processing (jam, canned products, baked product)

• It has been widely used in baked good, beverages, soft drinks, sugar preserves and confectionery, alcoholic
drinks, vinegar, pickles and sauces, dairy products, fruits, vegetables etc

• It has been banned in the USA and restricted levels of used in other countries (European) due to its
controversial safety issue
 Sucralose

• 1,6-dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-
galactopyranoside
• Made from sucrose by selective replacement of 3 OH with Cl, a process
that occurs with inversion of configuration at the 4 position of galacto-
analog
• It has 600 x sweeter than sucrose
• It has a pleasant, sugar-like, sweet taste with no un-pleasant aftertaste
• It is white, crystalline, non-hygroscopic, free-flowing powder, highly
soluble in water, ethanol and methanol, negligible effect on pH solution
and (sliglty lowering) surface tension
Sweetener safety

• All sweeteners are carefully studied and reviewed by numerous

scientific and regulatory bodies (example: JECFA , Codex) before
they are used in foods and beverages
• ADI (acceptable daily intake) can be used as a benchmark to
evaluate the actual intake of substance and as an aid in reviewing
possible additional uses for a food ingredient
Reference(s)

Varzakas T, Labropoulos A and Anestis S. 2012. Sweeteners, Nutritional

aspects, applications, and production technology. CRC Press Taylor &
Francis Group. New York

Nabors LO. 2012. Alternative sweeteners 4rd Edition. CRC Press Taylor &
Francis Group. New York