Chemistry Reference
In-Depth Information
thesamesweetnessbutdifferinsolubilityandsensitivitytopH.AGisrelativelystableandhighly
soluble in hot or cold water and in alcohol. It withstands temperatures above 105°C for a short
periodoftimeandprecipitatesatpHvaluesbelow4.5.MAGisusedinapplicationswherelowpH
andcolorruleoutAG.
Glycyrrhizinis50-100timessweeterthansucroseandhasaslowonsetofsweetnessfollowed
byalingeringlicorice-likeaftertaste(Table4.1).Itexhibitsasweetwoodylavor,whichlimitsits
useasapuresweetener.Glycyrrhizinenhancesfoodlavors,masksbitterlavors,andincreasesthe
perceived sweetness level of sucrose. It has the potential for providing functional characteristics
includingfoaming,viscositycontrol,gelformation,andpossiblyantioxidantcharacteristics.
Studieshavefocusedonthepharmacologicaleffectsofglycyrrhizinasantiulcer,antiinlammatory,
antiviral,anticariogenic,andantispasmodic.Italsohascorticoidactivity,inluencingsteroidmetabo-
lismtomaintainbloodpressureandvolumeandtoregulateglucose/glycogenbalance.Glycyrrhizin
canbehydrolyzedbyhumanintestinalmicrolorato18-β-glycyrrhetinicacidandtwomoleculesof
glucuronicacid.Afterreleaseoftheacids,thecompoundbindstoplasmaprotein,enterstheentero-
hepaticcirculation,andisalmostcompletelymetabolized.However,sideeffects,typicallyinvolving
cardiac dysfunction, edema, and hypertension, have been reported among subjects receiving high
dosesofglycyrrhizin-basedpharmaceuticalsorconsuminglargeamountsoflicorice-containingcon-
fectioneryorhealthproductsoveraprolongedperiod.
TheammoniumsaltofglycyrrhizinisapprovedasalavoringandlavorenhancerintheUnited
States.ItisontheFDA“generallyrecognizedassafe”(GRAS)list.Theuseofglycyrrhizinisper-
mittedinJapanandTaiwan.InJapan,itisusedasalavoringforhydrolyzedvegetableprotein,soy
sauce,andbeanpastetocontrolsaltiness.Atlevelsof30-300mg/kg,itenhancesthelavorofcocoa
and chocolate-lavored products, lavors and sweetens candy, confectionery, and beverages, and
masksthebittertasteofpharmaceuticals.Becauseofitspharmacologicalaction,itshouldbeused
inmoderateamountsasasweetener.GlycyrrhizinisusedinJapanandinothercountriesasasweet-
eningagent.IntheUnitedStates,itisapprovedforuseasalavorandlavorenhancerbelow4.5.
4.8 NeOheSperIDIN DIhYDrOChaLCONe
Citrus fruits contain bitter lavanone glycosides, all derivatives of the disaccharide 2-
O
-α-l-
rhamnopyranosyl-β-d-glucopyranose, neohesperidose. In 1963, Horowitz and Gentili found that
catalytic hydrogenation of the chalcone form gave dihydrochalcone neohesperidosides, several
ofwhichwereintenselysweet.Numerousdihydrochalconederivativesweresynthesizedfortaste
andtoxicitytrials,fromwhichNHDCemergedasapromisingsweetener.Itispreparedbyalka-
line hydrogenation of the bilavanoid neohesperidin present in Seville (bitter) oranges (
Citrus
aurantium
).
NHDC is a semisynthetic nonnutritive intense sweetener. Chemically, it is 1-[4-[[2-
O
-(6-
deoxy-α-l-mannopyranosyl)-β-d-glucopyranosyl]oxy]-2,6-dihydroxyphenyl]-3-(3-hydroxy-4-
methoxyphenyl)-1-propanone with the molecular formula C
28
H
36
O
15
and a molecular weight of
612.60(Figure4.6).NHDCshowsaslowbuildupofsweetness,risingfrom250to2000timesthat
ofa50g/Lsucrosesolution,butmorepersistent(Table4.1).Ithasapleasanttaste,lavor-modifying
properties,abilitytoimprovethesweetnessqualityandproile,andremarkablesynergisticeffects.
Itslavorenhancementhasbeenperceivedinseveralproducts,especiallyfruitlavors.NHDChas
theabilitytodecreasetheperceptionofbitterness,saltiness,sharp,andspicyattributes.Thesweet-
ness intensity of NHDC depends on many factors such as concentration, pH, and the product to
whichitisadded.Astheconcentrationincreases,thesweetnessofNHDCdecreasesrelativetothe
level of sucrose. Caffeine signiicantly enhances the sweetness of NHDC in certain soft drinks.
Athigherconcentrations,NHDChasalingeringmentholorlicorice-likeaftertasteandacooling
sensation, which distinguishes it from other sweeteners. However, modiications of the sensorial
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