Title: Alternative Sweeteners

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Neohesperidin Dihydrochalcone 99 they were limited to one single product or studied foods and beverages with unrealistically high sweetener concentrations. An analytical method to detect and quantitate neohesperidine DC in foodstuffs has been developed and validated, yielding adequate results in terms of precision, accuracy, selectivity, and ruggedness to quantitate neohesperidine DC both at flavoring and sweetening use levels in soft drinks (89). The method has successfully been assayed also in complex foods such as dairy products, confectionery, and fat-based foods that require selective extraction of the sweetener with appropriate solvents (dimethyl sulfoxide, methanol, and their blends with water). Acceptable recoveries (90%) were found in all tested samples both at flavoring and sweetening use levels. This method provides sufficient separation between the neohesperidine DC peak and the corresponding hydrolysis acid products. Neohesperidine DC is used as a minor component of sweetener blends and therefore at very low concentrations. However, HPLC techniques allow detection and quantitation of neohesperidine DC at levels below those that are normally used for sweetening and flavoring purposes. Thus, detection and quantitation limits for neohesperidine DC, determined by the method based on the standard deviation of the response and the slope, are 0.2 and 0.7 mg/l, respectively. These values are below the minimum concentration, which shows a technological function in the final food. Usually, extraction in dimethyl sulfoxide or alcohols is sufficient for selective extraction of neohesperidine DC; however, adsorption of neohesperidine DC onto Amberlite XAD and subsequent fractionation on Sephadex were judged to be essential steps for successful quantitation of neohesperidine DC in blackcurrant jam because of the fact that anthocyanin-related compounds may interfere with neohesperidine DC in crude extracts (36). VIII. AVAILABILITY AND PATENT SITUATION Neohesperidine DC is produced in industrial scale by Zoster, S. A. and marketed worldwide by Exquim, S. A. under the tradename of Citrosa ® . Both companies belong to the pharmaceutical group Ferrer Internacional, S. A. The original patents, which covered the manufacture of neohesperidine DC, have expired, although neohesperidine DC has a patent portfolio that covers its use and applications (63, 64, 68). DEDICATION This chapter is dedicated to the memory of Prof. Dr. Francisco Sabater Garcia.
100 Borrego and Montijano REFERENCES 1. RM Horowitz, B Gentili. Dihydrochalcone derivatives and their use as sweetening agents. US Patent No. 3,087,821 (April 30, 1963). 2. RM Horowitz. Relations between the taste and structure of some phenolic glycosides. In: JB Harborne, ed. Biochemistry of Phenolic Compounds. New York: Academic Press, 1964, pp 545–571. 3. RM Horowitz, B Gentili. Taste and structure in phenolic glycosides, 1. Agric Food Chem 17:696–700, 1969. 4. RM Horowitz, B Gentili. Phenolic glycosides of grapefruit: A relation between bitterness and structure. Arch Biochem Biophys 92:191–192, 1961. 5. RM Horowitz, B Gentili. Flavonoids of citrus VI. The structure of neohesperidose. Tetrahedron 19:773–782, 1963. 6. RM Horowitz, B Gentili. Flavonoid constituents of citrus. In: S Nagy, PE Shaw, MK Veldhuis, eds. Citrus Science and Technology. Vol. 1. Westport, CT: The AVI Publishing Company, 1977, 397–426. 7. RM Horowitz, B Gentili. Conversion of naringin to neohesperidin and neohesperidin dihydrochalcone. US Patent No. 3,375,242 (March 26, 1968). 8. L Krbechek, G Inglett, M Holik, B Dowling, R Wagner, R Riter. Dihydrochalcones: Synthesis of potential sweetening agents. J Agric Food Chem 16:108–112, 1968. 9. GH Robertson, JP Clark, R Lundin. Dihydrochalcone sweeteners: Preparation of neohesperidin dihydrochalcone. Ind Eng Chem Prod Res Devel 13:125–129, 1974. 10. K Veda, H Odawara. Neohesperidin from naringin. Jpn Kokai 75:154–261, December 12, 1975 [Chem Abstr 84:180574, 1976]. 11. RM Horowitz, B Gentili. Dihydrochalcone sweeteners from citrus flavanones. In: LO Nabors, RC Gelardi, eds. Alternative Sweeteners, 2nd ed. New York: Marcel Dekker, 1991, pp 97–115. 12. AHB Linke, S Natarajan, DE Eveleigh. A new screening agent to detect the formation of dihydrochalcone sweeteners by microorganisms. The Annual Meeting of the American Society of Microbiology, 1973, abstract No. 184, p 171. 13. E Lewinsohn, H Gavish, E Berman, R Fluhr, Y Mazur, J Gressel. Towards biotechnologically synthesized neohesperidin for the production of its dihydrochalcone sweetener. International Conference on Sweeteners. Los Angeles, CA: American Chemical Society, September 22–25, 1988, abstract No. 39. 14. E Lewinsohn, L Britsch, Y Mazur, J Gressel. Flavanone glycoside biosynthesis in Citrus. Plant Physiol 91:1323–1328, 1989. 15. E Lewinsohn, E Berman, Y Mazur, J Gressel. 7-glycosylation and (1-6) rhamnosylation of exogenous flavanones by undifferentiated Citrus cell cultures. Plant Science 61:23–28, 1989. 16. E Lewinsohn, L Britsch, Y Mazur, J Gressel. Flavanone glycoside biosynthesis in Citrus: Chalcone synthase, UDP-glucose-flavanone-7-O-glucosyl transferase and rhamnosyl transferase activities in cell-free extracts. Plant Physiol 91:1323–1328, 1989. 17. M Bar-Peled, E Lewinsohn, R Fluhr, J Gressel. UDP-rhamnose flavanone-7-O-glucoside-2′-O-rhamnosyl transferase, purification and characterization of an enzyme
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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
Page 62 and 63: Aspartame 49 day for 60-kg adults (
Page 64 and 65: Aspartame 51 mood, and behavior (88
Page 66 and 67: Aspartame 53 VI. WORLDWIDE REGULATO
Page 68 and 69: Aspartame 55 30. A Bar, C Biermann.
Page 70 and 71: Aspartame 57 67. HH Butchko, C Tsch
Page 72 and 73: Aspartame 59 104. AF Stokes, A Belg
Page 74: Aspartame 61 144. D Squillacote. As
Page 77 and 78: 64 Bopp and Price Figure 1 Structur
Page 79 and 80: 66 Bopp and Price Table 1 Regulator
Page 81 and 82: 68 Bopp and Price V. ADMIXTURE POTE
Page 83 and 84: 70 Bopp and Price and thickeners (1
Page 85 and 86: 72 Bopp and Price XII. METABOLISM C
Page 87 and 88: 74 Bopp and Price sodium cyclamate
Page 89 and 90: 76 Bopp and Price ied during the pa
Page 91 and 92: 78 Bopp and Price the studies invol
Page 93 and 94: 80 Bopp and Price 0.42 µg/ml and w
Page 95 and 96: 82 Bopp and Price 4. U.S. Patent No
Page 97 and 98: 84 Bopp and Price 48. SM Sieber, RH
Page 100 and 101: 6 Neohesperidin Dihydrochalcone Fra
Page 102 and 103: Neohesperidin Dihydrochalcone 89 Fi
Page 104 and 105: Neohesperidin Dihydrochalcone 91 Fi
Page 106 and 107: Neohesperidin Dihydrochalcone 93 in
Page 108 and 109: Neohesperidin Dihydrochalcone 95 ot
Page 110 and 111: Neohesperidin Dihydrochalcone 97 Ta
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Page 116 and 117: Neohesperidin Dihydrochalcone 103 5
Page 118 and 119: 7 Tagatose Hans Bertelsen and Søre
Page 120 and 121: Tagatose 107 the same type of Food
Page 122 and 123: Tagatose 109 in pigs according to m
Page 124 and 125: Tagatose 111 IV. USE OF D-TAGATOSE
Page 126 and 127: Tagatose 113 rinsing periods or dur
Page 128 and 129: Tagatose 115 anaerobic bacterial fe
Page 130 and 131: 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
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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
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178 Kinghorn et al. iol administere
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180 Kinghorn et al. cus mutans, or
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182 Kinghorn et al. a natural sweet
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11 Sucralose Leslie A. Goldsmith an
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Sucralose 187 Figure 2 Sweeteness i
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Sucralose 189 cant difference was f
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Sucralose 191 fructose, and/or insu
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Sucralose 193 Figure 4 Sucralose so
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Sucralose 195 Figure 6 Viscosities
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Sucralose 197 Table 2 Sucralose Int
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Sucralose 199 tively, compared with
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Sucralose 201 Figure 10 Breakdown o
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Sucralose 203 Table 3 Percent Mass
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Sucralose 205 Table 4 Initial Appli
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Sucralose 207 4. Sucralose Safety A
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210 Kinghorn and Compadre establish
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212 Kinghorn and Compadre grosvenor
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214 Kinghorn and Compadre form. Phy
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216 Kinghorn and Compadre of the de
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218 Kinghorn and Compadre Figure 5
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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
Page 555 and 556:
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
Page 563 and 564:
550 Index [Polyols] isomalt, 265-28
Page 565 and 566:
552 Index [Sucralose] safety, 189-1
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