Alitame is an artificial sweetener that is 2000 times sweeter than sucrose. It is a dipeptide composed of L-aspartic acid and D-alanine, attached to a thietanyl group. Alitame is heat stable, non-caloric, and does not promote tooth decay. It is used in foods and beverages as a sugar substitute. While considered safe, some studies have shown alitame can affect gut bacteria and impair glucose metabolism. Alitame received regulatory approval in several countries in the 1990s but was later withdrawn in the US.

1. ALITAME
MOKSHA CHIB
13FET1003
Artificial Sweetener
1

2. 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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3. 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]a
mino]-4-oxobutanoic
acid
L – Aspartic D- Alanine Amide

4. 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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5. 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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6. PREPARATION
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DIPK is Diisopropyl ketone

7. 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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8. 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.
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Solvent Solubility
(%w/v)
Water 13.1
Methanol 41.9
Ethanol 61.0
Propylene
glycol
53.7
Chloroform 0.02
N- heptane 0.001

9. 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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10. 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

11.  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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12. 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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13. 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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14. 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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15.  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

16. INCORPORATION 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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17. ALITAME17

18. 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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19. 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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20. 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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21. 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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22. THANK YOU !
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