Title: Alternative Sweeteners

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Stevioside 169 methods for the purification of stevioside entail initial extraction into an aqueous solvent, followed by refinement involving one or more of selective extraction into a polar organic solvent, decolorization, precipitation, coagulation, adsorption, ion exchange, and crystallization (1, 2). III. PHYSICAL AND ORGANOLEPTIC PROPERTIES, SOLUBILITY, AND STABILITY Although chemical work to determine the structural nature of stevioside began at the turn of the past century, more than 60 years elapsed before the structure of this compound was finally elucidated. A group at the National Institutes of Health in Bethesda, Maryland, was able to show that one sugar unit of stevioside occurs as a d-glucopyranosyl functionality attached β to a carboxyl group, whereas the second is a sophorose [2-O-(β-d-glucopyranosyl)-d-glucose] unit attached β to an alcoholic group on the aglycone (1, 2). The structure and stereochemistry of steviol (ent-13-hydroxykaur-16-en-19-oic acid), the aglycone obtained on the enzymatic hydrolysis of stevioside, were finally determined in 1963 (2). Isosteviol is produced from stevioside by acidic hydrolysis and is a ring-D rearranged isomer of steviol (2, 3). During the 1970s, additional sweet steviol glycoside analogs of stevioside were identified as S. rebaudiana leaf constituents, comprising rebaudiosides A and B, steviolbioside, rebaudioside C ( dulcoside B), rebaudiosides D and E, and dulcoside A (1, 2). Some evidence exists that rebaudioside B and steviolbioside are not native S. rebaudiana constituents but are formed by partial hydrolysis during the extraction process (3, 4). The structures of the sweet ent-kaurene glycosides of S. rebaudiana leaves are shown in Fig. 1. The sweet ent-kaurene glycosides occur at very high concentration levels in dried S. rebaudiana leaves, with approximate values for the four most abundant compounds being stevioside (5–10% w/w), rebaudioside A (2–4% w/w), rebaudioside C (1–2% w/w), and dulcoside A (0.4–0.7% w/w) (2). In pure form, stevioside is a white crystalline material with a melting point of 196–198°C, an optical rotation of 39.3 degrees in water, an elemental composition of C 38H 60O 18, and a molecular weight of 808.88 (2). Stevioside is only sparingly soluble in water but is highly soluble in ethanol. Rebaudioside A is considerably more water soluble than stevioside because it contains an additional glucose unit in its molecule (2). Stevioside is a stable molecule at 100°C when maintained in solution in the pH range 3–9, although it decomposes quite readily at alkaline pH levels of greater than 10 under these conditions (1). Both stevioside and its analog, rebaudioside A, have been found to be stable when formulated in acidulated beverages that were stored at 60°C for 5 days (2). Detailed stability profiles have been determined for stevioside when treated with dilute mineral acids and en-
170 Kinghorn et al. Figure 1 Structures of the eight sweet-tasting glycoside constituents of Stevia rebaudiana leaves. zymes (2). A large number of analytical methods are available for the determination of purity and stability of stevioside and rebaudioside A (1, 2). Stevioside has been rated as possessing about 300 times the relative sweetness intensity of 0.4% w/v sucrose, although its sweetness intensity varies with concentration and the compound exhibits some bitterness and an undesirable aftertaste (1). The sweetness intensities (i.e., sweetening power relative to sucrose, which is taken as 1) of the other seven S. rebaudiana sweet principles have
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ISBN: 0-8247-0437-1 This book is pr
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iv Preface these sweeteners are bei
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vi Contents 7. Tagatose 105 Hans Be
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Contributors Sue E. Andress The Nut
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Contributors xi Carolyn M. Merkel M
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1 Alternative Sweeteners: An Overvi
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Overview 3 II. RELATIVE SWEETNESS P
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Overview 5 IV. INTERNATIONAL REGULA
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Overview 7 V. U.S. REGULATION OF SW
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Overview 9 General recognition of s
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Overview 11 the maximum dietary lev
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2 Acesulfame K Gert-Wolfhard von Ry
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Acesulfame K 15 Figure 3 Acesulfame
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Acesulfame K 17 Figure 4 Sweetness
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Acesulfame K 19 The acute oral toxi
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Acesulfame K 21 Table 2 Stability o
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Acesulfame K 23 were preferred over
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Acesulfame K 25 losses during bakin
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Acesulfame K 27 All methods describ
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Acesulfame K 29 24. Report of the S
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3 Alitame Michael H. Auerbach Danis
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Alitame 33 IV. SOLUBILITY At the is
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Alitame 35 Figure 3 Alitame and asp
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Alitame 37 Figure 5 Metabolism of a
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Alitame 39 autonomic, gastrointesti
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4 Aspartame Harriett H. Butchko, W.
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Aspartame 43 Figure 2 Principal con
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Aspartame 45 A wide range exists ov
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Aspartame 47 Figure 4 Dietary intak
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Aspartame 49 day for 60-kg adults (
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Aspartame 51 mood, and behavior (88
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Aspartame 53 VI. WORLDWIDE REGULATO
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Aspartame 55 30. A Bar, C Biermann.
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Aspartame 57 67. HH Butchko, C Tsch
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Aspartame 59 104. AF Stokes, A Belg
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Aspartame 61 144. D Squillacote. As
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64 Bopp and Price Figure 1 Structur
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66 Bopp and Price Table 1 Regulator
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68 Bopp and Price V. ADMIXTURE POTE
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70 Bopp and Price and thickeners (1
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72 Bopp and Price XII. METABOLISM C
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74 Bopp and Price sodium cyclamate
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76 Bopp and Price ied during the pa
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78 Bopp and Price the studies invol
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80 Bopp and Price 0.42 µg/ml and w
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82 Bopp and Price 4. U.S. Patent No
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84 Bopp and Price 48. SM Sieber, RH
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6 Neohesperidin Dihydrochalcone Fra
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Neohesperidin Dihydrochalcone 89 Fi
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Neohesperidin Dihydrochalcone 91 Fi
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Neohesperidin Dihydrochalcone 93 in
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Neohesperidin Dihydrochalcone 95 ot
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Neohesperidin Dihydrochalcone 97 Ta
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Neohesperidin Dihydrochalcone 99 th
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Neohesperidin Dihydrochalcone 101 c
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Neohesperidin Dihydrochalcone 103 5
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7 Tagatose Hans Bertelsen and Søre
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Tagatose 107 the same type of Food
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Tagatose 109 in pigs according to m
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Tagatose 111 IV. USE OF D-TAGATOSE
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Tagatose 113 rinsing periods or dur
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Tagatose 115 anaerobic bacterial fe
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Tagatose 117 The intestines of both
Page 132 and 133: Tagatose 119 Table 1 Relative Sweet
Page 134 and 135: Tagatose 121 D. Hygroscopicity Taga
Page 136 and 137: Tagatose 123 Table 2 Heat of Soluti
Page 138 and 139: Tagatose 125 In conclusion, tagatos
Page 140: Tagatose 127 24. BB Jensen, B Buema
Page 143 and 144: 130 Stargel et al. Figure 1 Compari
Page 145 and 146: 132 Stargel et al. Figure 2 Matrix
Page 147 and 148: 134 Stargel et al. ness of neotame
Page 149 and 150: 136 Stargel et al. Figure 4 Taste p
Page 151 and 152: 138 Stargel et al. Table 1 Solubili
Page 153 and 154: 140 Stargel et al. study strains in
Page 155 and 156: 142 Stargel et al. to 10,000 µg/pl
Page 157 and 158: 144 Stargel et al. for general use
Page 160 and 161: 9 Saccharin Ronald L. Pearson PMC S
Page 162 and 163: Saccharin 149 proved for use in the
Page 164 and 165: Saccharin 151 was added to sodium d
Page 166 and 167: Saccharin 153 Table 2 Economics of
Page 168 and 169: Saccharin 155 Table 4 Saccharin Adm
Page 170 and 171: Table 6 Flavor Profile and Cost Com
Page 172 and 173: Saccharin 159 Figure 5 Hydrolysis o
Page 174 and 175: Saccharin 161 malian repellant (52,
Page 176 and 177: Saccharin 163 REFERENCES 1. GE DuBo
Page 178: Saccharin 165 67. GP Schoenig, et a
Page 181: 168 Kinghorn et al. herbarium speci
Page 185 and 186: 172 Kinghorn et al. V. USE AND ADMI
Page 187 and 188: 174 Kinghorn et al. sulting in the
Page 189 and 190: 176 Kinghorn et al. Figure 2 Struct
Page 191 and 192: 178 Kinghorn et al. iol administere
Page 193 and 194: 180 Kinghorn et al. cus mutans, or
Page 195 and 196: 182 Kinghorn et al. a natural sweet
Page 198 and 199: 11 Sucralose Leslie A. Goldsmith an
Page 200 and 201: Sucralose 187 Figure 2 Sweeteness i
Page 202 and 203: Sucralose 189 cant difference was f
Page 204 and 205: Sucralose 191 fructose, and/or insu
Page 206 and 207: Sucralose 193 Figure 4 Sucralose so
Page 208 and 209: Sucralose 195 Figure 6 Viscosities
Page 210 and 211: Sucralose 197 Table 2 Sucralose Int
Page 212 and 213: Sucralose 199 tively, compared with
Page 214 and 215: Sucralose 201 Figure 10 Breakdown o
Page 216 and 217: Sucralose 203 Table 3 Percent Mass
Page 218 and 219: Sucralose 205 Table 4 Initial Appli
Page 220: Sucralose 207 4. Sucralose Safety A
Page 223 and 224: 210 Kinghorn and Compadre establish
Page 225 and 226: 212 Kinghorn and Compadre grosvenor
Page 227 and 228: 214 Kinghorn and Compadre form. Phy
Page 229 and 230: 216 Kinghorn and Compadre of the de
Page 231 and 232: 218 Kinghorn and Compadre Figure 5
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220 Kinghorn and Compadre Figure 7
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226 Kinghorn and Compadre sweet tas
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230 Kinghorn and Compadre 5. O Tana
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232 Kinghorn and Compadre 41. S Nir
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13 Erythritol Milda E. Embuscado an
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Erythritol 237 The commercial produ
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Table 2 Properties of Erythritol Co
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Erythritol 241 used to obtain the d
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Erythritol 243 crose stabilized and
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Erythritol 245 Figure 4 (A) Rate of
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Table 6 Assessment Criteria for the
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Table 7 Summary of Pivotal Toxicity
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Erythritol 251 VI. FOOD AND PHARMAC
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Erythritol 253 5. C Servo, J Pabo,
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14 Hydrogenated Starch Hydrolysates
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Figure 1 (a) Chemical structures fo
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Hydrogenated Starch Hydrolysates an
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15 Isomalt Marie-Christel Wijers* P
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Isomalt 267 GPM depends on the isom
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Isomalt 269 IV. PHYSICO-CHEMICAL PR
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Isomalt 271 temperature than sucros
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Isomalt 273 C. Diabetics A number o
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Isomalt 275 Figure 7 Changes in wei
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Isomalt 277 C. Chewing Gum Sticks,
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Isomalt 279 isomalt is significantl
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Isomalt 281 der Sorbit-Toleranz ges
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16 Maltitol Kazuaki Kato Towa Chemi
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Maltitol 285 Like the other polyols
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Maltitol 287 of shape over time), h
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Maltitol 289 results of this confer
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Maltitol 291 available on certain p
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Maltitol 293 Table 3 Worldwide Stat
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Maltitol 295 alcohol. Unpublished r
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298 Mesters et al. Figure 1 The che
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300 Mesters et al. rium and equal m
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302 Mesters et al. sugars are then
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304 Mesters et al. Figure 2 Telemet
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306 Mesters et al. Figure 3 Moistur
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308 Mesters et al. Figure 6 Viscosi
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310 Mesters et al. tose are the mai
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312 Mesters et al. Figure 8 The wat
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314 Mesters et al. food containing
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18 Sorbitol and Mannitol Anh S. Le
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Sorbitol and Mannitol 319 Figure 2
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Table 1 Physical Properties of the
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Sorbitol and Mannitol 323 Figure 4
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Sorbitol and Mannitol 325 bases are
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Sorbitol and Mannitol 327 is used a
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Sorbitol and Mannitol 329 ‘‘cap
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Sorbitol and Mannitol 331 that mann
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Sorbitol and Mannitol 333 Mannitol
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19 Xylitol Philip M. Olinger Polyol
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Xylitol 337 Milled forms of xylitol
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Xylitol 339 Table 2 Solubility of S
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Xylitol 341 tol in a fluoride tooth
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Xylitol 343 The recognition of xyli
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Xylitol 345 tion of the availabilit
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Xylitol 347 grow and metabolize opt
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Xylitol 349 VIII. USE OF XYLITOL AS
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Xylitol 351 IX. USE OF XYLITOL IN P
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Xylitol 353 Human tolerance of high
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Xylitol 355 29. CS Gong, TA Claypoo
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Xylitol 357 71. JDB Featherstone, T
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Xylitol 359 112. JS Van der Hoeven.
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Xylitol 361 tans omz 176 by xylitol
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Xylitol 363 BL Horecker, K Lang, Y
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Xylitol 365 of Certain Food Additiv
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368 White and Osberger II. MANUFACT
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370 White and Osberger scribe impro
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372 White and Osberger Figure 1 Cyc
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374 White and Osberger When asparta
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376 White and Osberger Table 5 Temp
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378 White and Osberger Figure 3 Met
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380 White and Osberger Figure 5 Com
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382 White and Osberger Table 6 Glyc
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384 White and Osberger Table 8 Low-
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386 White and Osberger F. Confectio
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388 White and Osberger In 1993, Vui
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390 White and Osberger 18. AL Forbe
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392 Buck Table 1 Market Division be
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394 Buck Table 3 World HFS Consumpt
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396 Buck Figure 3 Production of 42%
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398 Buck Table 4 Typical Characteri
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400 Buck Table 5 Effect of Temperat
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402 Buck Table 7 International Soci
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404 Buck Because of the high purity
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406 Buck VII. APPLICATIONS HFCS rep
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408 Buck is a benefit and in other
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410 Buck 1986. This evaluation conc
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22 Isomaltulose William E. Irwin* P
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Isomaltulose 415 Figure 2 Isosweet
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Isomaltulose 417 Figure 3 Solubilit
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Isomaltulose 419 Figure 6 Plasma in
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Isomaltulose 421 6. Dreissig VW, Lu
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424 Richards and Dexter various pla
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426 Richards and Dexter from assays
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428 Richards and Dexter desiccation
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430 Richards and Dexter 2. Taste Qu
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432 Richards and Dexter parative da
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434 Richards and Dexter Table 3 Com
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436 Richards and Dexter dissipate t
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438 Richards and Dexter unpublished
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440 Richards and Dexter IX. SHELF-L
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Figure 7 Egg white (95 g) was mixed
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444 Richards and Dexter Figure 10 B
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446 Richards and Dexter Figure 12 O
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448 Richards and Dexter Figure 14 T
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450 Richards and Dexter XIII. CARIO
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452 Richards and Dexter tions was s
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454 Richards and Dexter activity, a
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456 Richards and Dexter E. 14-day T
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458 Richards and Dexter 3. J Leibow
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460 Richards and Dexter 41. LM Crow
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24 Mixed Sweetener Functionality Ab
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Mixed Sweetener Functionality 465 2
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Mixed Sweetener Functionality 467 T
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Mixed Sweetener Functionality 471 F
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Mixed Sweetener Functionality 479 I
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25 Aspartame-Acesulfame: Twinsweet
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Aspartame-Acesulfame: Twinsweet 483
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26 Polydextrose Helen Mitchell Dani
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Polydextrose 501 Table 1 Approximat
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Polydextrose 503 at 25°C. Polydext
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Polydextrose 505 Figure 4 Hygroscop
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Polydextrose 507 Table 5 Functional
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Polydextrose 509 F. Fiber Polydextr
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Polydextrose 511 providing bulk, mo
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Polydextrose 513 H. Soft Candy The
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Polydextrose 515 B. International T
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Polydextrose 517 chemical and econo
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520 Deis I. FAT IS ESSENTIAL AND FU
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522 Deis Figure 1 Ingredient suppor
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524 Deis binding water, thus provid
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526 Deis The U.S. Department of Agr
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528 Deis stabilizer, thickener, or
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530 Deis mouth feel and rate of gel
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532 Deis Figure 4 Structure of glyc
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534 Deis Table 4 General Categories
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536 Deis ninths of the fat availabl
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538 Deis the same function in all f
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540 Deis 28. Anon. Glycerine: like
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542 Index [Alitame] solubility, 33
Page 557 and 558:
544 Index [Erythritol] gastrointest
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546 Index [High fructose corn syrup
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548 Index Mogrosides, 211-213 prope
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550 Index [Polyols] isomalt, 265-28
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552 Index [Sucralose] safety, 189-1
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