Title: Alternative Sweeteners

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Less Common High-Potency Sweeteners 229 Figure 20 Structure of hoduloside I. (Glc d-glucopyranosyl; rha l-rhamnopyranosyl.) alternosides I–X, have been isolated and characterized from the roots of Gymnema alternifolium (67). About 10 sweetness-inhibitory dammarane-type triterpenoid sweetness inhibitors have now been isolated and purified from the leaves of Z. jujuba, with all of these being equal to or less potent than ziziphin itself (65). Several dammarane-type sweetness inhibitors have also been reported in the leaves of H. dulcis, with the parent compound, hoduloside I, being one of the most potent (65). However, ziziphin and hoduloside I are somewhat less potent than gymnemic acid I as sweetness-inhibitory agents (65). Recently, a series of novel antisweet oleanane-type triterpene glycosides, sitakisosides I–XX, has been reported from the stems of Stephanotis lutchinensis Koidz var. japonica (68–70). REFERENCES 1. L O’Brien Nabors, GE Inglett. A review of various other alternative sweeteners. In: L O’Brien Nabors, RC Gelardi, eds. Alternative Sweeteners. New York: Marcel Dekker, 1986, pp 309–323. 2. AD Kinghorn, CM Compadre. Less common sweeteners. In: L O’Brien Wabors, RC Gelardi, eds. Alternative Sweeteners, 2nd ed., Revised and Expanded. New York: Marcel Dekker, 1991, pp 151–171. 3. GR Fenwick, J Lutomski, C Nieman. Liquorice, Glycyrrhiza glabra L.—composition, uses, and analysis. Food Chem 38:119–143, 1990. 4. K Mizutani. Biological properties, production, and use of chemical constituents of licorice. In: C-T Ho, T Osawa, M-T Huang, RT Rosen, eds. Food Phytochemicals for Cancer Prevention II, Symposium Series No. 547. Washington, DC: American Chemical Society, 1994, pp 322–328.
230 Kinghorn and Compadre 5. O Tanaka. Improvement of taste of natural sweeteners. Pure Appl Chem 69:675– 683, 1997. 6. K Mizutani, T Kuramoto, Y Tamura, N Ohtake, S Doi, N Nakaura, O Tanaka. Sweetness of glycyrrhetic acid 3-O-d-monoglucuronide and the related glycosides. Biosci Biotech Biochem 58:554–555, 1994. 7. K Mizutani. Maruzen Pharmaceuticals Co., Ltd., Fukuyama, Hiroshima, Japan. Private communication. 8. T Machinami, T Suami. Glycyrrhetinic acid derivatives and low-calorie sweeteners containing them. Jpn Kokai Tokkyo Koho, JP10028548, Mar 2, 1998, 6 pp. 9. R Nakamura, Y Amino, T Takemoto. Glycyrrhetinic acid derivatives and sweeteners containing them. Jpn Kokai Tokkyo Koho, JP11000131, Jan 6, 1999, 3 pp. 10. R Suttisri, M-S Chung, AD Kinghorn, O Sticher, Y Hashimoto. Periandrin V, a further sweet triterpene glycoside from Periandra dulcis. Phytochemistry 34:405– 408, 1993. 11. Y-H Choi, RA Hussain, JM Pezzuto, AD Kinghorn, JF Morton. Abrusosides A-D, four novel sweet-tasting triterpene glycosides from the leaves of Abrus precatorius. J Natl Prod 52:1118–1127, 1989. 12. AD Kinghorn, N Kaneda, N-I Baek, EJ Kennelly, DD Soejarto. Noncariogenic intense natural sweeteners. Med Res Rev 18:347–360, 1998. 13. RL Smith, P Newburne, TB Adams, RA Ford, JB Hallogan, and the FEMA Expert Panel. GRAS flavoring substances 17. Food Technol 50:72–81, 1996. 14. GJ de Klerck, MG Nieuwenhuis, JJ Beutler. Hypokalaemia and hypertension associated with the use of liquorice flavoured chewing gum. BMJ 314:731–732, 1997. 15. JJ Chamberlain, IZ Abolnik. Pulmonary edema following a licorice binge. West J Med 167:184–185, 1997. 16. AD Kinghorn, F Fullas, RA Hussain. Structure-activity relationships of highly sweet natural products. In: A-ur-Rahman, ed. Studies in Natural Product Chemistry, Vol. 15, Structure and Chemistry (Part C). Amsterdam: Elsevier, 1995, pp 1–41. 17. K Matsumoto, R Kasai, K Ohtani, O Tanaka. Minor cucurbitane-glycosides from fruits of Siraitia grosvenori (Cucurbitaceae). Chem Pharm Bull 38:2030–2032, 1990. 18. J Si, D Chen, Q Chang, L Shen. Isolation and determination of cucurbitane-glycosides from fresh fruits of Siraitia grosvenorii. Zhiwu Xuebao 38:489–494, 1996. 19. CM Fischer, HJ Harper, WJ Henry Jr, MK Mohlenkamp Jr, K Romer, RL Swaine Jr. Sweet beverages and sweetening compositions. PCT International Application WO9418855, Sep 1, 1994, 33 pp. 20. M Yoshikawa, T Murakami, T Ueda, H Shimoda, J Yamahara, H Matsuda. Development of bioactive functions in Hydrangea Dulcis Folium. VII. Absolute stereostructures of 3S-phyllodulcin, 3R- and 3S-phyllodulcin glycosides, and 3R- and 3S-thunberginol H glycosides from the leaves of Hydrangea macrophylla Seringe var. thunbergii Makino. Heterocycles 50:411–418, 1999. 21. A Bassoli, L Merlini, G Morini, A Vedani. A three-dimensional receptor model for isovanillic sweet derivatives. J Chem Soc Perkin Trans II:1449–1454, 1998. 22. T Naoki, T Nakano, K. Goto, T Seisho. Syntheses of dihydroisocoumarins, ()-hydrangenol and ()-phyllodulcin, utilizing an annelation reaction of enami-
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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
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Tagatose 119 Table 1 Relative Sweet
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Tagatose 121 D. Hygroscopicity Taga
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Tagatose 123 Table 2 Heat of Soluti
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Tagatose 125 In conclusion, tagatos
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Tagatose 127 24. BB Jensen, B Buema
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130 Stargel et al. Figure 1 Compari
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132 Stargel et al. Figure 2 Matrix
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134 Stargel et al. ness of neotame
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136 Stargel et al. Figure 4 Taste p
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138 Stargel et al. Table 1 Solubili
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140 Stargel et al. study strains in
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142 Stargel et al. to 10,000 µg/pl
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144 Stargel et al. for general use
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9 Saccharin Ronald L. Pearson PMC S
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Saccharin 149 proved for use in the
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Saccharin 151 was added to sodium d
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Saccharin 153 Table 2 Economics of
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Saccharin 155 Table 4 Saccharin Adm
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Table 6 Flavor Profile and Cost Com
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Saccharin 159 Figure 5 Hydrolysis o
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Saccharin 161 malian repellant (52,
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Saccharin 163 REFERENCES 1. GE DuBo
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Saccharin 165 67. GP Schoenig, et a
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168 Kinghorn et al. herbarium speci
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170 Kinghorn et al. Figure 1 Struct
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172 Kinghorn et al. V. USE AND ADMI
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174 Kinghorn et al. sulting in the
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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
Page 239 and 240: 226 Kinghorn and Compadre sweet tas
Page 241: 228 Kinghorn and Compadre Figure 18
Page 245 and 246: 232 Kinghorn and Compadre 41. S Nir
Page 248 and 249: 13 Erythritol Milda E. Embuscado an
Page 250 and 251: Erythritol 237 The commercial produ
Page 252 and 253: Table 2 Properties of Erythritol Co
Page 254 and 255: Erythritol 241 used to obtain the d
Page 256 and 257: Erythritol 243 crose stabilized and
Page 258 and 259: Erythritol 245 Figure 4 (A) Rate of
Page 260 and 261: Table 6 Assessment Criteria for the
Page 262 and 263: Table 7 Summary of Pivotal Toxicity
Page 264 and 265: Erythritol 251 VI. FOOD AND PHARMAC
Page 266 and 267: Erythritol 253 5. C Servo, J Pabo,
Page 268 and 269: 14 Hydrogenated Starch Hydrolysates
Page 270 and 271: Figure 1 (a) Chemical structures fo
Page 272 and 273: Hydrogenated Starch Hydrolysates an
Page 278 and 279: 15 Isomalt Marie-Christel Wijers* P
Page 280 and 281: Isomalt 267 GPM depends on the isom
Page 282 and 283: Isomalt 269 IV. PHYSICO-CHEMICAL PR
Page 284 and 285: Isomalt 271 temperature than sucros
Page 286 and 287: Isomalt 273 C. Diabetics A number o
Page 288 and 289: Isomalt 275 Figure 7 Changes in wei
Page 290 and 291: 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
Page 555 and 556:
542 Index [Alitame] solubility, 33
Page 557 and 558:
544 Index [Erythritol] gastrointest
Page 559 and 560:
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
Page 565 and 566:
552 Index [Sucralose] safety, 189-1
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