Low Calorie Nonnutritive Sweeteners - Sweeteners: Nutritional Aspects, Applications, and Production Technology - page 83

drinksthatmaintainalowpH.ACS-K[ I ]hasexcellentstabilityunderhightemperaturesandgood
solubilitythatmakesitsuitablefornumerousproducts.Itisapprovedforuseinfoodandbeverage
productsinabout90countriesincludingtheUnitedStates,Switzerland,Norway,UnitedKingdom,
Canada,Australia,andtheEU.

4.3 aLItaMe

Alitame[l-α-aspartyl- N -(2,2,4,4-tetramethyl-3-thioethanyl)-d-alaninamide]isanaminoacid-
basedsweetener(Figure4.2)developedbyPizerCentralResearchfroml-asparticacid,d-alanine,
and2,2,4,4-tetraethylthioethanylamine.Aterminalamidegroupinsteadofthemethylestercon-
stituentofASPwasusedtoimprovethehydrolyticstability.Theincorporationofd-alanineasa
secondaminoacidinplaceofl-phenylalaninehasresultedinoptimumsweetness.Theincreased
stericandlipophilicbulkonasmallringwithasulfurderivativehasprovidedaverysweetproduct
andgoodtastequalities.
TheformulaofalitameisC 14 H 25 O 4 N 3 S,withamolecularweightof331.06.Itisproducedunder
thebrandnameAclame.Itisacrystalline,odorless,andnonhygroscopicpowder,withagoodsolu-
bilityinmostpolarsolventssuchaswater(130g/LatpH5.6)andalcohol.Alitameis2000times
sweeterthansucrose,12timessweeterthanASP,and6timessweeterthansaccharin.Ithasaclean
sweet taste with no unpleasant aftertaste. It is blended with other sweeteners such as saccharin,
cyclamate,andACS-Ktomaximizethequalityofsweetness.
AlitameoffersseveralbeneitssuchasstabilityathightemperaturesandabroaderpHrange.
Forinstance,itisstableforoverayearatpH6-8androomtemperatureandwithstandspasteuriza-
tion.However,prolongedstorageofacidicsolutionsathightemperaturesorincombinationwith
certainingredients(hydrogenperoxideorsodiumbisulite)mayproduceoff-lavors.Inthepresence
ofhighlevelsofreducingsugars,alitamecanundergoMaillardreactions.
Alitame is noncariogenic. From an oral intake, 7%-22% is unabsorbed and excreted in the
feces. The remainder is hydrolyzed to aspartic acid and alanine amide. The aspartic acid is nor-
mallymetabolized,andthealanineamideisexcretedintheurineasasulfoxideisomer,sulfone,or
conjugatedwithglucuronicacid.Theincompleteabsorptionandmetabolismresultinacorevalue
of1.4kcalg −1 .
TheJointExpertCommitteeonFoodAdditives(JECFA)concludedthatalitamewasnotcarci-
nogenicanddidnotshowreproductivetoxicity.In1996,anADIof0-1mg/kgofbodyweightwas
allocated.ItisapprovedforuseinAustralia,NewZealand,Mexico,andChina.Afoodadditive
petitionwassubmittedtotheFDAin1986,andapprovalisawaited.Inthepetition,theestimated
daily intake is 0.34 mg/kg of body weight, which represents the amount if alitame is the only
sweetenerinthediet.Thelevelatwhichnoobservedadverseeffectsoccurinanimalsis100mg/
kg.Potentialusesincludebakedgoods,bakingmixes,hotandcoldbeverages,drybeveragemixes,
tabletopsweeteners,chewinggum,candies,frozendesserts,andpharmaceuticals.Alitamehasbeen
approvedforuseinsomecountriessuchasAustralia,Mexico,NewZealand,andChina,butnotin
theUnitedStatesortheEU.

O CH 3

H 3 C

HO NH CH 3

NH

S

O NH 2 O

H 3 C

CH 3

Figure 4.2 Chemical structure of alitame.