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ALITAMEMOKSHA CHIB 13FET1003

Artificial Sweetener

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WHAT IS ALITAME ?

Alitame is a non-nutritive, artificial, intensive sweetener.

Unlike Aspartame, it is a protein and a dipeptide. It has been allotted the E number 956. Used as low calorie sweetener as it gives the same taste

as table sugar but without any calories. Chemical name : L-α-Aspartyl-N-(2,2,4,4-tetramethyl-3-

thietanyl)-D-alaninamide, hydrated Chemical formula : C14H25N3O4S · 2.5 H2O

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STRUCTURE Alitame is a dipeptide of L-Aspartic acid & D-Alanine.

Attached to alanine is a amine (2,2,4,4 tetramethylthietanyl amine).

It was developed by Pfizer in the early 1980s and is currently marketed in some countries under the brand name Aclame.

It was synthesized after the accidental discovery of Aspartame.

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IUPAC Name:

(3S)-3-amino-4-[ [(1R)-1-methyl-2-oxo-2-[(2,2,4,4-tetramethyl-3-thietanyl)amino]ethyl]amino]-4-oxobutanoic acid L –

Aspartic D- Alanine Amide

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STRUCTURE Dipeptides are generally not sweet but Alitame’s

high sweetness potency can be attributed to the presence of amide.

Reasons why Alitame attains its sweet taste: due to the small to moderate ring size presence of small-chain branching α to the

amine-bearing carbon introduction of the sulfur atom into the

carbocyclic ring.

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PREPARATION Alitame is prepared by a multistep synthesis

involving the reaction between two intermediates, (S)-[2,5-dioxo-(4-thiazolidine)] acetic acid and (R)-2-amino-N-(2,2,4,4-tetramethyl-3-thietanyl) propanamide.

The final product is isolated and purified through crystallization of an alitame-4-methylbenzenesulfonic acid molecules, followed by additional purification steps, and finally recrystallization from water.

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PREPARATION

ALITAME

DIPK is Diisopropyl ketone

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ORGANOLEPTIC PROPERTIES Alitame is a crystalline, odourless, non hygroscopic

powder.

It is about 2000 times sweeter than Sucrose & about 10 times sweeter than Aspartame.

The sweetness of Alitame is of a high quality, sucrose-like, without accompanying any bitter or metallic notes. Its sweet taste develops rapidly in the mouth and lingers for sometime.

Alitame has been found to exhibit synergy when combined with both Acesulfame K and Cyclamate. High-quality blends with other sweeteners including saccharin are also effective.

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SOLUBILITY

At the isoelectric pH (5.6), Alitame is very soluble in water.

It shows excellent solubility in polar solvents.

But it is virtually insoluble in lipophilic solvents.

The solubility rapidly increases with temperature.

ALITAME

Solvent Solubility (%w/v)

Water 13.1

Methanol 41.9

Ethanol 61.0

Propylene glycol

53.7

Chloroform 0.02

N- heptane 0.001

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DECOMPOSITION PATHWAYS The major pathway involves

hydrolysis of the aspartylalanine dipeptide bond to give aspartic acid and alanyl-2,2,4,4-tetramethylthietane amide.

The α, β aspartic rearrangement also occurs to give β aspartic isomer of alitame, which again hydrolyses to give the same product.

No cyclization to diketopiperazine or hydrolysis of the alanine amide bond is detectable in solutions of alitame that have undergone up to 90% decomposition.

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STABILITY Its half-life under hot or acidic conditions is about twice

as long as aspartame's. At acid pH (2–4), alitame solution half-lives are more

than twice those of aspartame. As the pH increases, this stability advantage greatly

increases. In particular in the neutral pH range (5–8), alitame is completely stable for more than 1 year at room temperature.

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Alitame and Aspartame stability in buffer solution at 23°C

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This shows that alitame can survive the thermal and pH conditions of the baking process & has a heat stability advantage over aspartame.

Alitame is sufficiently stable for use in hard and soft candies, heat-pasteurized foods, and in neutral pH foods processed at high temperatures, such as sweet baked goods.

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COMPATIBILITY The compatibility of alitame with a given recipe will

depend on the actual ingredients present and the thermal and pH exposure involved in the manufacturing process.

Reaction with reducing sugars

High levels of reducing sugars, such as glucose and lactose, may react with alitame in heated liquid or semi liquid systems, such as baked goods, to form Maillard reaction products.

Similar reactions are shown by flavour aldehydes at high levels.

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Production of off-flavors

Prolonged storage of alitame in acidic liquid beverage recipes may result in production of off flavours.

Levels of off-flavorant(s) are below the limits of modern analytical detection.

Substances which may produce off-flavors on storage with alitame in liquid products are hydrogen peroxide, sodium bisulfite, ascorbic acid, and some types of caramel colour at pH less than 4.0.

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METABOLISM

Alitame is well absorbed after oral administration to the mouse, rat, dog, or man.

Most of an oral dose (77%–96%) is excreted in urine as a mixture of metabolites. The remainder (7%–22%) is excreted in the faeces, primarily as unchanged alitame.

The maximum calorific value given by alitame is 1.4kcal/ gram.

Alitame is metabolized to aspartic acid which is used in amino acid metabolism, making alitame caloric.

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Metabolism of alitame gives alanine amide fragments.

In rats & dogs, alanine amide is partially acetylated.

In man, it is partially conjugated with glucoronic acid.

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Metabolism of alitame

16INCORPORATION IN FOODS Alitame is used in a wide range of foods and beverages,

including bakery wares, water-based flavored drinks, dairy-based drinks, cream, edible ices, jams, confectionery.

Being a low calorie sweetener, it is incorporated in diabetic foods.

Alitame is used in the rolling compound of chewing

gums from 0.01% - 20%.

Due to high thermal stability, it finds many more applications in bakery products and in dairy based products which undergo pasteurization (UHT) during processing.

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BENEFITS Has zero calories per

serving & thus can be included in diabetic diet.

Has zero glycemic index. Not harmful for teeth i.e

doesn’t lead to dental caries.

Heat stable Non carcinogenic & not

a mutagen. No teratogenic effects No major toxicity Considered to be a

better alternative than Aspartame in many ways.

CONCERNS Although it contains

zero calories, still it doesn’t appear to be effective against diabetes and obesity.

Studies have shown that alitame affects the bacteria in the bowel in adverse ways.

Tests showed impaired glucose metabolism in animals and humans after moderate consumption over several weeks.

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SAFETY Non carcinogenic, teratogenic, embryogenic and

mutagenic. Unlike aspartame, alitame does not contain phenylalanine,

and can therefore be used by people with phenylketonuria (PKU).

Considered to have no or very low toxicological effects in either rats or humans.

In 1996, JECFA set an acceptable ADI of 1mg/kg bw/day. In the 59th meeting occurring in JUNE 2002, JECFA

postponed making ADI or other toxicological recommendations about alitame until findings of a 90 day tolerance study were made available.

In the FDA petition, the estimated daily intake as a sole sweetener in all products is 0.34mg/kg bw/day.

The level at which no observable adverse effects occurred in animals was 100mg/kg.

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REGULATORY STATUS In 1986 a Food Additive Petition was submitted to the US

FDA requesting broad clearance for alitame (Federal Register 1986).

The petition requested approval of alitame as a sweetener and flavoring in specified foods in amounts necessary to achieve the intended effect and in accordance with good manufacturing practice.

Alitame was approved for use in food and beverages in Australia (1993); in Mexico (1994); in New Zealand (1994); in People’s Republic of China (1994); in Indonesia (1995); in Colombia (1996), and in Chile (1997).

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REFERENCES Alternative Sweeteners, 4th edition by Lyn O’ Brien

Nabors. Sweeteners and Sugar Alternatives in Food Technology

by Helen Mitchell Ellis, J. W. (1995). "Overview of Sweeteners". Journal of

Chemical Education 72 (8) "Notice of withdrawal of petition: docket No. FDA-1986-

F-0277 (formerly docket No. 1986F-0364)"(pdf). Food and Drug Administration.

FAO org page- JECFA Additives

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THANK YOU !

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