Artificial and natural Sweetners

presented by Mankaran singh CT Institute of Pharmaceutical Sciences Punjab, India

ARTIFICIAL SWEETNERS
Acesulfame potassium 2. Alitame 3. Aspartame 4. Cyclamate 5. Dulcin 6. Glucin 7. Neohesperidin dihydrocholocone 8. Neotame 9. P -4000 10. Saccharin 11. Sucralose 12. Steria 13. Aspartame
1.

NATURAL SUGAR SUBSITUTES

Brazzein 2. Curculin 3. Erythritol 4. Glycyrrhizin 5. Inulin 6. Laitol 7. Isomalt 8. Luo han guo 9. Mabinlin 10. Maltitol 11. Mannitol 12. Dentadin 13. Sorbitol 14. Stevia 15. tagatose
1.

16. Thaumatin 17. xtlitol

Starch based
HFCS 55 /isoglucose HFCS 42 Glucose syrups High maltose syrups

Aspartame Acesulphame K Cyclamate Saccharin Sucralose TwinSweet Neotame Alitame Sucrose

Thaumatin Neohesperidine Stevioside Glycyrrhizin Brazzein

High Intensity

Fructose Glucose / dextrose Trehalose Tagatose Glucose/fructose/sucrose extracts from fruits

Mannitol Isomalt Maltitol Xylitol Sorbitol Lactitol Sorbitol and maltitol syrups Erythritol Approved in EU

Sugar alcohols

Saccharides

Sweetness
HFCS Sucrose Sorbitol Aspartame Acesulfame-K Alitame Thaumati n

0,1
Glucose

10

100
Saccharin

1000

10000

Fructose Glucose Syrup

Cyclamate

Sucralose

Neotame

ARTIFICIAL SWEETNERS
1.Aspartame
A dipeptide (L--aspartyl-L-phenylalanine methyl ester) Intestinal esterases hydrolyze aspartame to aspartic acid, methanol,

and phenylalanine. Aspartame is approximately 200 times sweeter than sucrose, or table sugar. Aspartame is a methyl ester of the aspartic acid / phenylalanine dipeptide . In 1981, approved by FDA FDA requires that foods that contain aspartame have the prominent display of the following label: "PHENYLKETONURICS: CONTAINS PHENYLALANINE"

Molecular formula

C14H18N2O5

Molar mass

294.3 g mol1

Density

1.347 g/cm3

Melting point

246247 C

Acidity (pKa)

4.5-6.0

Solubility in water Sparingly soluble Solubility slightly soluble in ethanol

Stability and ph
At room temperature its stability is good at pH values of

between 3.4 and 5 and it is maximum at pH 4.3. At pH below 3.4 the dipeptide is hydrolysed and at a pH greater than 5, cyclisation occurs with the formation of diketopiperazine. In both cases, this transformation results in the loss of sweetness. The solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/ml at 25C) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/ml at 25C. Aspartame is very stable in the dry state: at 105C a loss of approximately 5% (formation of diketopiperazine) is observed after 100 hours of treatment. At 120C, a 50% loss is obtained after 80 hours of treatment.

2.ALITAME( C14H25N3O4S)PENDING APPROVAL

Alitame is an artificial sweetener developed by Pfizer in the

early 1980s and currently marketed in some countries under the brand name Aclame. Like aspartame, alitame is an aspartic acid-containing dipeptide. Most dipeptides are not sweet, but the unexpected discovery of aspartame in 1965 led to a search for similar compounds that shared its sweetness. Alitame is one such second-generation dipeptide sweetener. Neotame, developed by the owners of the NutraSweet brand, is another.

ALITAME( C14H25N3O4S)PENDING APPROVAL properties

White, crystalline powder, odourless or having a slight

characteristic odour. Approximately 2000 times sweeter than sucrose.

Solubility = Freely soluble in water and in ethanol pH =Between 5.0 and 6.0 (5 in 100ml soln) Specific rotation = [] 25, D: between +40 and +50,

1% (w/v) in water

3CYCLAMATE (BANNNED)30X SWEETNESS

Cyclamate is the sodium or calcium salt of cyclamic

acid ( cyclohexanesulfamic acid), which itself is prepared by the sulfonation of cyclohexylamine. This can be accomplished by reacting cyclohexylamine with either sulfamic acid or sulfur trioxide.

Log P (o/w) Solubility(water)

0.98 (est ) 200 g/l (20 C)

Molar mass

201.22 g/mol

Bulk density
pH value

600 - 700 kg/m3

5.5 - 7.5 (100 g/l, H2O, 20 C)

SOLUBILITY=Cyclamic acid is very sparingly soluble in water, and is slowly hydrolyzed in hot water. Sodium cyclamate and calcium cyclamate are both freely soluble in water.

4. NEOHESPERIDIN DIHYDROCHOLOCONE
Neohesperidin dihydrochalcone, sometimes

abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus. Neohesperidin dihydrochalcone is up to 1000 times as sweet as sucrose, but it has a number of other properties that limit its use as a sweetener. 1. First, it has an intense cooling effect on the tongue. 2.Second, it has licorice-like and bitter offtastes. Third, it is slow in onset and has a lingering taste that make it decidedly not sucrose-like.

PROPERTIES
Appearance: white to pale yellow powder

Solubility: in cool water is 0.4-0.5 g/l but it has high solubility in hot water, also soluble, in ethanol, water:ethanol solutions and alkaline water solutions.

Odor: Odorless
Stability: very stable in crystalline form and in water solutions

Molecular Weight

612.5764400

logP (o/w)

3.09

Maximised Survey-derived Daily Intakes (MSDI-EU)

12.00 (g/capita/day)

Metling point

156.00 - 158.00 C

5. NEOTAME
Neotame is about 8,000 times sweeter than sugar, so

only 6 milligrams is needed to sweeten a typical 12 ounce soft drink. Neotame is an artificial sweetener made by NutraSweet t hat is between 7,000 and 13,000 times sweeter than sucrose (table sugar). In the European Union, it is known by the E number E961.Neotame is moderately heat stable and extremely potent. Neotame is rapidly metabolized and completely eliminated and does not appear to accumulate in the body. It is chemically similar to the artificial sweetener aspartame but is used at vastly lower levels and is more stable.

6. SACCHARIN
Saccharin is an artificial sweetener. The basic

substance, benzoic sulfilimine, has effectively no food energy and is much sweeter than sucrose, but has an unpleasant bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products such as drinks, candies, biscuits, medicines, and toothpaste.

PROPERTIES
pH: Aqueous solution is neutral to slightly alkaline to litmus Appearance :White crystalline solid
Molecular formula C7H5NO3S

Molar mass

183.18 g mol1

Density

0.828 g/cm3

Melting point

228.8-229.7

Solubility in water

1 g per 290 Ml

7.SUCRALOSE (600X SWEETNESS) APPROVED FDA 1998

Sucralose is a zero-calorie artificial sweetener. In the

European Union, it is also known under the E number (additive code) E955. Sucralose is approximately 600 times as sweet as sucrose (table sugar), twice as sweet as saccharin, and 3.3 times as sweet as aspartame. It is stable under heat and over a broad range of pH conditions. Therefore, it can be used in baking or in products that require a longer shelf life. The commercial success of sucralose-based products stems from its favorable comparison to other low-calorie sweeteners in terms of taste, stability, and safety.

Properties
Safety : Sucralose has undergone extensive safety testing. It appears to be only partially absorbed, followed by excretion in the kidneys. At high temperature in aqueous solution, sucralose is hydrolyzed to a limited extent, producing 4-chloro-4deoxy-galactose and 1,6-dichloro-1,6-dideoxy-fructose.
Molecular formula Molar mass Melting point Solubility in water C12H19Cl3O8 397.64 g/mol 125 C, 398 K, 257 F 283 g/L (20 C)

8.STEVIA( FDA APPROVED)

Stevia is the only natural sweetner available in the

market. Stevia is a south american native sweetner plant of sunflower family. It is used for sweetening for centuries in Paraguay and has been in use since last 400 years across the world. It is the only sweetner which does not have any side effect. The raw stevia leaves are around 35 - 40 times sweeter than sugar, stevia extract are sweet upto 300 times of ordinary sugar. The stevia is safest low calorie sweetner without any side effect.

 PROPERTIES
Mineral content: Iron, manganessium and cobaltus Molecular weight: 804 Formula: C 38 H 60 O 18

It keeps its flavour stable under high and low

temperatures. Stevia doesnt ferment. It is soluble to water, alcohol. Calories: 0 Saturated fat: 0 Sugars: 0 Cholesterol: 0 Carbohydrates: 0

9. ACESULFAME POTASSIUM(FDA APPROVED)

Acesulfame potassium is a calorie-free artificial sweetener, also

known as Acesulfame K or Ace K (K being the symbol for potassium), and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number (additive code) E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG (now Nutrinova). In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C4H4KNO4S and a molecular weight of 201.24 g/mol. Acesulfame K is 180-200 times sweeter than sucrose (table sugar)

PROPERTIES
Appearance = white crystalline powder
Molecular formula Molar mass Density Melting point Solubility in water Heavey Metals logP (o/w) Boiling Point Flash Point C4H4KNO4S 201.242 1.81 g/cm3 225 C, 498 K, 437 F 270 g/L at 20 C < 1 mg/kg Pb -0.31 (est) 332.00 to 334.00 C. @ 760.00 mm Hg 311.00 F. TCC ( 155.00 C. )

10. GLUCIN
Glucin is the name of an artificial sweetening agent

similar to saccharin that was used in the early 20th century.The substance is a sodium salt derived from coal tar. It is composed of a mixture of mono- and disulfonic acids with a chemical formula of C19H16N4. It typically appears as a light brown powder, easily soluble in water. SOLUBILITY=It is insoluble in ether and chloroform. Glucin is about three hundred times sweeter than cane sugar.

11. Dulcin (FDA BANNED)

It was banned due to putative carcinogenicity, which

the warning label touts as one of saccharin's dangers as well. If you take a look at refused FDA imports from China, you can see that some food imports are rejected because of their dulcin content! It is 250X sweeter than sucrose.

NATURAL SWEETNERS

Novel sugar sweeteners

D-tagatose has a chemical structure similar to fructose

Trehalose is a disaccharide found in mushrooms

Products containing these sweeteners cannot be

labeled as sugar free D-FRUCTOSE D-TAGATOSE

Trahalose

Basic Saccharides
Monosaccharides

(glucose, fructose, galactose)

Disaccharides

(sucrose, maltose, lactose)

Trisaccharides

(raffinose)
Tetrasaccharides

Glucose

Fructose

(stachyose)
Pentasaccharides

(verbascose)

BASIC SACCHARIDES
Monosaccharides
(simple sugars)

glucose (galactose) fructose

Disaccharides (two mono's) saccharose /

sucrose, normal sugar lactose, milk sugar maltose

Starch (>10 glucose units)

Other natural sweeteners:

Honey, molasses, maple syrup,

corn syrup, high fructose corn syrup Sugar alcohols or polyols, such as mannitol, sorbitol, isomalt

1.Barley Malt Syrup

Sprouted barley. Maltose, glucose, complex carbohydrates; 65 percent maltose, 30 percent complex carbohydrate, 3% protein. Dark brown, thick and sticky; strong distinctive flavor, like molasses. Half as sweet as white sugar.

2.Blackstrap Molasses
70 percent sucrose. The dark, syrupy "leftovers" from the sugar-refining process. Marginally qualifies as a natural sweetener, but it does contain most, if not all, of the redeeming value of the original cane plant--such as thiamine, riboflavin, niacin, pantothenic acid, calcium, iron, magnesium, potassium, and chromium, as well as other micronutrients. Very strong flavor. A source of iron.

3. Brown Rice Syrup Brown rice and various enzymes. Maltose, glucose, complex carbohydrates; 50 percent maltose and 37 percent complex carbohydrate. Amber colored syrup with mild "butterscotch" flavor. Half as sweet as white sugar. 4. Date Sugar Ground, dehydrated dates. Sucrose, glucose, fructose, complex carbohydrates. Contains folic acid. Mahogany color, coarse granules, kinda moist. 5.Evaporated White Grape Juice and Brown Rice Syrup (Fruitsource, manufactured by Fruitsource Confections, Inc.) 33 percent or more complex carbohydrate. Yellowish-white, granulated sweetener;

 6. Evaporated Whole Cane Juice (Rapadura,

Sucanat) Sugar cane, water removed. Minerals and molasses are retained. Sucrose and invert sugars*. Amber-colored coarse granules, mild molasses-like taste. WARNING: Just in: Sucanat may not be truly "evaporated" whole cane juice as it once was; have been informed that method has been switched to "crystallization" which requires the adding back of molasses to an essentially refined product. Rapadura, manufactured by Rapunzel, continues to be 100% organic and is obtained through an evaporation process.

7. Honey Extracted from flower nectar by bees. Fructose, glucose, sucrose. Color and taste depend upon flower source. 20% to 60% sweeter than white sugar; use less! 8. Maple Syrup From sap of maple trees (not the imposters in grocery stores!); about 40 gallons of sap produce 1 gallon of syrup; 60% sucrose plus invert sugars; dark brown with maple flavor; high in potassium and calcium. 9. Maple Syrup Granules (Maple Sugar) Dehydrated maple syrup. 93% sucrose, 1% to 3% invert sugars. Light brown granules with maple flavor.

10. Stevia Stevioside

A perennial shrub of the aster family; available in whole or broken leaves, coarse ground, powder extract, or liquid extract; 8-300 times sweeter than table sugar (depending on quality and whether it is leaf or extract) but with 0 calories; sweetening attributes are the glycosides (Steviosides, Rebaudiosides and a Dulcoside).

Functionality highlights Alternatives to Sucrose

HFCS / Isoglucose
Adds water Offers sweetening, bulking, and preservation

Glucose syrup
Bulking, but half sweetness of sugar

Sugar Alcohols
Special sensory effects
Bulking Reduced calorie effect

High Intensity Sweeteners

Only sweetening Varying stability with pH, time and heat Off-taste and after-taste Blending improve taste profiles No effective calories

THANK YOU