Sweetening agents ester

In nature, the amino acids are combined to give proteins with hundreds or even thousands of amino acids in each one. Small assemblies of amino acids are known as peptides and die amide bond that links them is called a peptide bond. One important dipeptide is the sweetening agent aspartame, whose synthesis was discussed in Chapter 25. It is composed (and made) of the amino acid aspartic acid (Asp) and the methyl ester of phenylalanine. Only this enantiomer has a sweet taste and it is very sweet indeed—about 160 times as sweet as sucrose. 

Aspartame (a-L-aspartyl-L-phenylalanine 1-methyl ester) is a sweetening agent that is roughly 200 times sweeter than sucrose. Routes for preparing this compound are described in U.S. 3,492,131, U.S. 4,440,677 (both to G. D. Searle Co.), and U.S. 5,476,961 (to the NutraSweet Company). Determine which route gives the lowest cost of production. 

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. 

Methyl acetoacetate (MAA) and ethyl acetoacetate (EAA) are the most widely used esters they are found ia the pharmaceutical, agricultural, and allied industries. Both esters are used extensively as amine protecting agents ia the manufacture of antibiotics and synthetic sweeteners (Dane Salts) (147). Principal outiets for MAA are the manufacture of the organophosphoms insecticide dia2inon [33341-5] (148,149) and the uracil herbicides bromacil [31440-9] and terbacil [5902-51-2] (150,151) (see Insect conztiol technology Herbicides). 

A wide variety of sulfamate esters have been synthesised and screened as herbicides, pharmaceutical agents and sweeteners (see Chapter 11, p. 240). Sulfamates containing a primary amino group (124) are conveniently prepared by condensation of the appropriate alcohol with sulfamoyl chloride (125) in DMF in the presence of sodium hydride (Scheme 50). An illustrative example is provided by the conversion of substituted p-phenylethanols (126) to the corresponding sulfamates (127) (Scheme 50). Compounds of type (127) exhibit anticonvulsant and carbonic anhydrase activity and may be useful in the treatment of epilepsy and glaucoma. Sulfamoyl chlorides (125) may be prepared by treatment of amines or amine hydrochlorides with sulfuryl chloride (128). An analogous reaction also occurs with dialkyl sulfonamides (129) (Scheme 51). 

Use Synthesis of butyrate ester perfume and flavor ingredients, pharmaceuticals, deliming agent, disinfectants, emulsifying agents, sweetening gasolines. 

L-Aspartic acid is an industrially important, large-volume, chiral compoimd. Worldwide production of L-aspartic acid was approximately 11,000 metric tons in 1993 and is estimated to grow to 13-15 thousand tons in 1998 [1], More than half of all the aspartic acid produced is consumed by the United States market. The primary use of aspartic acid is in the production of aspartame (A -i.-a-aspar-tyl-L-phenylalanine, methyl ester), a high-potency sweetener. Other uses of l-aspartate include dietary supplements, pharmaceuticals, production of alanine, antibacterial agents, and lubricating compounds. 

L-Aspartate is used in parenteral nutrition and food additives, and as a starting material for the low-calorie sweetener aspartame, aspartyl-phenylalanine methyl ester. Recently, the possibility of using L-aspartate as a raw material for polymer production was studied very hard since it has three reactive residues in the molecule and the resulted polymers could be biodegradative. It is used as a detergent and chelating or water treating agent. 

Uses Alkyd resins paints dynamite ester gums perfumery lubricants softener bacteriostat penetrant emollient antifreeze prod, of antibiotics plasticizer for regenerated cellulose film, sodium silicate foundry resins solvent (printing inks) humectant (tobacco, starch adhesives, textile sizes) solvent, humectant, plasticizer, bodying agent for foods, food pkg., cosmetics plasticizer, solvent, solubilizer, preservative for pharmaceuticals PU crosslinker heat costabilizer (PVC) sweetener preservative plasticizer in food-contact coatings Use Level 0.2-65.7% (topicals), 1-50% (liq. orals), 50% (parenterals), 7-10% (dentifrices), 0.5-3.0% (ophthalmics)... 

The annual world production of L-aspartate is estimated to be 7,0001. L-Aspartate is used as an enteral and parenteral nutrient, a food additive, and a starting material for the low-calorie sweetener aspartame (aspartylphenylalanine methyl ester). It is also used as a raw material to synthesize detergent and for chelating or water treatment agents. 

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