Equal - Aspartame

One of the most widely used artificial sweeteners available today is a dipeptide, consisting of a unit of aspartic acid linked to a unit of phenylalanine. The carboxyl group of the phenylalanine moiety has been converted to the methyl ester. This substance is known commercially as aspartame, but it is also sold under the trade names NutraSweet and Equal. Aspartame is about 200 times sweeter than sucrose. It is found in diet soft drinks, puddings, juices, and many other foods. Unfortunately, aspartame is not stable when heated, so it is not suitable as an ingredient in cooking. Other dipeptides that have structures similar to that of aspartame are many thousands of times sweeter than sucrose. 

An estimation of the amount of amino acid production and the production methods are shown ia Table 11. About 340,000 t/yr of L-glutamic acid, principally as its monosodium salt, are manufactured ia the world, about 85% ia the Asian area. The demand for DL-methionine and L-lysiae as feed supplements varies considerably depending on such factors as the soybean harvest ia the United States and the anchovy catch ia Pern. Because of the actions of D-amiao acid oxidase and i.-amino acid transamiaase ia the animal body (156), the D-form of methionine is as equally nutritive as the L-form, so that DL-methionine which is iaexpensively produced by chemical synthesis is primarily used as a feed supplement. In the United States the methionine hydroxy analogue is partially used ia place of methionine. The consumption of L-lysiae has iacreased ia recent years. The world consumption tripled from 35,000 t ia 1982 to 100,000 t ia 1987 (214). Current world consumption of L-tryptophan and i.-threonine are several tens to hundreds of tons. The demand for L-phenylalanine as the raw material for the synthesis of aspartame has been increasing markedly. 

Fmctose is sweeter than sucrose at low temperatures (- S C) at higher temperatures, the reverse is tme. At 40°C, they have equal sweetness, the result of a temperature-induced shift in the percentages of a- and P-fmctose anomers. The taste of sucrose is synergistic with high intensity sweeteners (eg, sucralose and aspartame) and can be enhanced or prolonged by substances like glycerol monostearate, lecithin, and maltol (19). 

Aspartame. Aspartame [22839-47-0] [53906-69-1] (APM, L-aspartyl-L-phenylalanine methyl ester) (1), also known under the trade names of NutraSweet and EQUAL, is the most widely used nonnutritive sweetener worldwide. This dipeptide ester was synthesized as an intermediate for an antiulcer peptide at G. D. Searle in 1965. Although this compound was known in the literature, its sweet taste was serendipitously discovered when a chemist licked his finger which was contaminated with it. Many analogues, especially the more stable esters, were made (6) and their taste qualities and potencies determined. It was the first compound to be chosen for commercial development. Following the purchase of G. D. Searle by Monsanto, the aspartame business was split off to become a separate Monsanto subsidiary called the NutraSweet Company. 

Currently, aspartame is used in tabletop sweeteners (Equal in the U.S. F.ga in Quebec, Canada and Canderal in Europe and the tJK,). Aspartame currently is incorporated as the exclusive sweetening ingredient in nearly all diet soft drinks in the United States. In other countries, it may be blended, with saccharin at a level close to 50% of the saccharin level. Soft-dnnk manufacturers have taken some measures to enhance stability by raising pH slightly and by more closely controlling the inventory for carbonated soft drinks Notable differences in sweetness are perceived at a 40% loss in aspartame level. 

Aspartame is an intense sweetener first discovered in 1965 by J. Schlatter it is available under the brand names of Nutrasweet , Equal , and Canderel . Chemically, aspartame is N-L-a-aspartyl-L-phenylalanine methyl ester (Fig. 1), withamolecularformulaofC14H 805N2 (MW = 294.30). It is a white, odorless, crystalline powder. It is slightly soluble in water and sparingly soluble in alcohol. The solubility increases as the pH is lowered (2,6,57). It has 100-200 times the sweetness of sucrose and exhibits a sweet, clean taste and a sweetness profile similar to that of sucrose, without bitter or metallic aftertaste (Table 1). However, it displays a slow onset of sweetness coupled with lingering sweet taste. It extends and intensifies tastes and enhances fruit flavors. Aspartame exhibits synergism, a superior taste profile, and improved stability when used with other sweeteners (1,4,14,55,75). 

Aspartyl phenylalanine-l-methyl ester, better known as aspartame, is an artificial sweetener with a worldwide production exceeding 15 000 tpa. It is marketed under the trade names Nutrasweet, Canderel, and Equal. This dipeptide, made of aspartic... 

Procedure The assay is performed by separately injecting equal volumes (about 20 pL) of the Standard Solution and the Test Solution into the chromatograph, recording the chromatograms, and measuring the responses for the major peaks. The percentage of aspartame related compound A in the test article is calculated using ... 

Dissolve about 10 mg of the sweetener Equal in 1 mL of 3 M HC1 in a test tube. Heat it with a Bunsen burner to a boil for 30 sec., but make sure that the liquid does not completely evaporate. Cool the test tube and label it Hydrolyzed Aspartame. ... 

On plate A you will spot samples of (1) phenylalanine, (2) aspartic acid, (3) leucine, (4) aspartame in Equal, and (5) the hydrolyzed aspartame you prepared in step no. 1. On plate B you will spot samples of Diet Coke on lanes (1) and (4), aspartic acid on lane (2), aspartame in Equal on lane (3), and the hydrolyzed aspartame you prepared previously on lane (5). 

Aspartame solution dissolve 150 mg Equal sweetener powder in 25 mL distilled water... 

Procedure Separately inject equal 20-p.L portions of Impurity Standard Preparation and Sample Preparation into the chromatograph, and record the chromatograms (the approximate retention time of 5-benzyl-3,6-dioxo-2-piperazineacetic acid is 4 min, and the approximate retention time of Aspartame is 11 min). Measure the peak area response of 5-benzyl-3,6-dioxo-2-piperazineacetic acid in each chromatogram. Calculate the percentage of 5-benzyl-3,6-dioxo-2-piperazineacetic acid in the sample by the formula... 

Procedure Inject about 20-pL portions of the Other Related Substances Standard Preparation and the Sample Preparation into the chromatograph, and record the chromatogram for a time equal to twice the retention time of Aspartame. In the chromatogram obtained from the Sample Preparation, the sum of the responses of all secondary peaks, other than that for 5-benzyl-3,6-dioxo-2-piperazineacetic acid, is not more than the response of the Aspartame peak obtained in the chromatogram from the Other Related Substances Standard Preparation. 

Draw the products formed by acidic hydrolysis of aspartame, the artificial sweetener used in Equal and many diet beverages. One of the products of this hydrolysis reaction is the amino acid phenylalanine. Infants afflicted with phenylketonuria cannot metabolize this amino acid, so it accumulates, causing mental retardation. When the affliction is identified early, a diet limiting the consumption of phenylalanine (and compounds like aspartame that are converted to it) can make a normal life possible. 

Aspartame (NutraSweet , Equal ), A-u-a-Aspartyl-L-Phenylalanine methyl ester, is 200 times sweeter than sucrose and, unlike saccharin, has no aftertaste. Its aqueous solubility is adequate for formulation purposes. It is stable in the solid form, but its stability in... 

There is published research on both sides of the toxicity question regarding aspartame, with almost equal numbers of articles claiming toxicity and safety. Most studies address controlled conditions where aspartame exposure could be localized. The foods people eat, however, are never restricted to ingestion of single species and mixture effects may indeed be responsible for the disparities of the test results. The differences in test results are believed to be because of ingestion of aspartame with varying other unidentified chemical species or quantities of other chemicals. 

Aspartame. [Nutrasweet]. (3-amino-n-(a-carboxyphenethyl)succinamic acid n-methyl ester, stereoisomer aspartylphenylalanine methyl ester n-l-a-aspartyl-l-phenylalanine 1-methyl ester canderel dipeptide sweetener Equal (TM) methyl aspartylphenylalanate 1-methyl n-l-a-as-partyl-l-phenylalanine Nutrasweet (TM) sweet dipeptide). C14H18N205. 

Amino-N-(a-methoxycarbonylphenethyl) succinamic acid 3-Amino-N-(a-carboxyphenethyl)succinamic acid N-methyl ester APM Asp-phe-ome Aspartam Aspartame Aspartame, L,L-a- Aspartamo Aspartamum Aspartylphenylalanine methyl ester L-Aspartyl-L-phenylalanine methyl ester Canderel CCRiS 5456 DIpeptide sweetener EINECS 245-261-3 Equal HSDB 3915 Methyl aspartylphenylalanate Methyl L-aspartyl-L-phenylalanine Methyl L-a-aspartyl-L-phenylalanate Methyl N-L-a-aspartyl-L-phenylalaninate 1-Methyl N-L-a-aspartyl-L-phenylalanate Nutrasweet L-Phenylalanine, L-a-aspartyl-, 2-methyl ester L-Phenylalanine, N-L-a-aspartyl-, 1-methyl ester SC 18862 Succinamic acid, 3-amino-N-(a-carboxyphenethyl)-, N-methyl ester, Sweet dipeptide Tri-sweet, A sweetening agent Crystals mp = 246-247° [a]8 = -2,3° (IN HCI). Searte 6.D. Co. 

Fig. 6.3-13 Dosage forms of pressure agglomerated artificial sweetener (aspartame) left) tablets and tablet dispenser, right) granules and portion packages. (Equal is a registered trademark of Merisant Co.)...

Aspartame, the sweetener used in the commercial products NutraSweet and Equal , is 160 times sweeter than sucrose. What products would be obtained if aspartame were hydrolyzed completely in an aqueous solution of HCl ... 

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