Chemistry Reference
In-Depth Information
O
H
HO
OH
Me
O
O
O
OH
OMe
HO
O
HO
OH
OH
O
HO
Figure 4.6
Chemical structure of NHDC.
propertiesofNHDCarepossiblebytheadmixtureofbulksweeteners,certainlavors,andother
taste-modifyingfoodadditivessuchasgluconates,aminoacids,ornucleotides.Italsoshowssyner-
gismwithsaccharin,ASP,cyclamate,sucralose,ACS-K,andsugaralcohol.
NHDCisanonhygroscopiccolorlesscrystallinesolid.Itissparinglysolubleinwater(0.50g/L)
at20°Cbutishighlysolubleat80°C(650g/L).Itisalsosolubleinalcoholandaqueousalkali,but
ahighersolubilityisachievedinethanol-watermixturesthaninwaterorethanolalone.Wherea
highersolubilityisrequired,monobasicsaltsmaybeusedthatarefreelysolubleinwaterandexhibit
ashorterdurationofsweetnessthantheparentcompound.ThesolubilityofNHDCmayalsobe
enhancedbydissolvingitinglycerolandpropyleneglycol,aswellasbyusingitinmixtureswith
readilywater-solublepolyolssuchassorbitol.Interestingly,thesebulksweetenersalsoactastaste
modiiersofNHDCbyreducingitsmenthol-likeaftertaste.
NHDCpresentshighstabilityatpH2-6.Itisstableundermostfood-processingandstorage
conditionsandwithstandspasteurization,ultrahightemperatureprocesses,andthenormalshelf
lifeofsoftdrinks.Itisstableduringfermentationofyogurtbutundergoeshydrolysisathighacidity
andelevatedtemperatures,yieldinghesperetindihydrochalcone,hesperetindihydrochalcone-4ʹ-β-
d-glucoside,rhamnose,andglucose.
NHDCisnoncariogenicandhasacaloricvalueof2kcalg
−1
.Littleofthecompoundisabsorbed
unchangedfromthesmallintestine.Aftercleavageoftheglycosidicsidechainbyintestinalmuco-
sal or bacterial glycosidases, the residual primary metabolites are partly excreted unchanged in
thebileandpartlymetabolizedfurther.Standardtoxicitytestshavesuggesteditssafety.In1987,
the Scientiic Committee for Food of the Commission of the European Communities allocated
anADIof0-5mgperkilogramofbodyweight.ItiscurrentlyapprovedforuseintheEuropean
Communities,Sweden,Switzerland,Morocco,andTunisia.
Owingtoitshighlyintenseandlong-lastingsweetness,NHDCisnormallyusedatconcentra-
tionsoflessthan100mg/kg.Onlyinchewinggumarehigherlevelsrequiredbecauseofitsslow
releasefromthegumbase.Foruseinsoftdrinks,NHDChasbeenrecommendedincombination
with other sweeteners at a concentration of 20 mg/kg. Owing to its ability to reduce bitterness
andtoitslavor-enhancingproperties,NHDCisanidealsweetenerforgrapefruitororangejuice.
Promising results have been reported from its use in fruit-lavored yogurts. In tabletop products,
theadditionofsmallamountsofNHDCmayresultinsigniicantsavingsbecauseofitssynergistic,
sweetness-enhancingeffect.Ithasbeenusedinjuice,softdrinks,dairyproducts,desserts,confec-
tionery,spreads,jams,chewinggum,chocolate-basedproducts,andicecream.
NHDCisasemisyntheticsweetenerpreparedfromneohesperidinornaringin,twolavanones
extractedfromcitruspeel.Inaqueoussolutions,NHDCisstableinthepHrange2.5-3.5.NHDC
iscurrentlyallowedformanyapplicationswithintheEU.IntheUnitedStates,itisapprovedfor
lavoringfoodproducts.
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