Sweeteners neotame

One of the most efficient methods for oxidation of primary alcohols to either aldehydes or carboxylic acids is the one, commonly known as the Anelli oxidation. This reaction is carried out in a two-phase (CH2Cl2/aq.buffer) system utilizing TEMPO/NaBr as a catalyst and NaOCl as the terminal oxidant The new system described here is an extension of the Anelli oxidation, but surprisingly, does not require the use of any organic solvents and replaces the KBr co-catalyst with the more benign, Na2B40y (Borax). The use of the new cocatalyst reduces the volume of the buffer solution and eliminates completely the need of a reaction solvent. The new system was successfully applied in the industrial synthesis of the 3,3-Dimethylbutanal, which is a key intermediate in the preparation of the new artificial sweetener Neotame. 

Another artificial sweetener, Neotame, is a modification of the aspartame structure. The addition of a large alkyl group to the amine group prevents enzymes from breaking the amide bond between aspartic acid and phenylalanine. Thus, phenylalanine is not produced when Neotame is used as a sweetener. Very small amounts of Neotame are needed because it is about 10 000 times sweeter than sucrose. 

Neotame is an artificial sweetener designed to overcome some of the problems with aspartame. The dimethylbutyl part of the molecule was added to block the action of peptidases, enzymes that break the peptide bond between the two amino acids aspartic acid and phenylalanine. This reduces the availability of phenylalanine, eliminating the need for a warning on labels directed at people who cannot properly metabolize phenylalanine. 

Neotame does not break down with the heat of cooking, another drawback to aspartame. It is also thirty times sweeter than aspartame, so less is needed to sweeten a product. 

Neotame is about eight thousand times sweeter than sugar, so only 6 milligrams is needed to sweeten a typical 12-ounce soft drink. 

Neotame is used in tabletop sweeteners, frozen desserts, chewing gum, candy, baked goods, fruit spreads, and ready-to-eat cereals. 

In some cases, yeast preparations which contain a high amount of nucleotides can be used to increase saltiness in combination with masking ofiF-notes of KCl [30]. Additionally, use of low amounts of fruit acids may reduce the bad taste of KCl-containing food preparations [31]. Usage of low amounts of sweeteners such as thaumatin [32] or neotame [33] was described to mask the ofiF-taste of KCl. 

Formulators in most markets now have a wide range of sweeteners available to use either alone or in combination. As Figures 4.1 and 4.2 show, the main intense sweeteners in use in soft drinks today are acesulfame K, aspartame, saccharin and cyclamate. Currently of less importance commercially (either because they are new to the market or because they have not found significant use in soft drinks), but still approved for use in soft drinks in some markets, are thaumatin, neohesperidin diliy-diochalcones, alitame, stevioside, sucralose and neotame. 

Neotame is characterised by an intensely sweet taste with a lingering liquorice back-taste, which is more noticeable when it is used as a sole sweetener or at high levels. Combinations with other bulk and intense sweeteners improve the taste quality. Generally, acceptable products can be made without major reformulation using up to 25% of sweetener provided by neotame (The NutraSweet Company, 2003). 

In the United States the FDA granted general use approval for neotame as a sweetener and flavour enhancer in July 2002. At the time of writing it is also approved in Australia, New Zealand, China, Mexico, Costa Rica and Puerto Rico. Neotame was submitted to the EU SCF in 2001 for evaluation and to date no evaluation has been published. Poland has granted temporary approval for neotame and it is also approved in the Czech Republic and Romania. 

Fig. 2 Use of chimeric T1R2 T1R3 receptors to determine regions critical for sweetener response. Responses to human (H, blue), rat (R, red) or human-rat chimeric T1R2 T1R3 receptors to a sucrose, aspartame, or neotame, b sucrose or cyclamate, and c sucrose (Sue) or acesulfame potassium (AceK) in the absence or presence of lactisole (Lac). Equivalent numbers of cells were imaged for each receptor-ligand pair. (Adapted from Xu et al. 2004, with permission. Copyright 2004 National Academy of Sciences, USA)...

The amide bond, (a) NutraSweet, the dipeptide aspartame, is a moiecuie composed of two amino acids joined by an amide (peptide) bond, (b) Neotame, a newiy approved sweetener, is aiso a dipeptide. One of the amino acids has been modified so that it is safe for use by phenyiketonurics. 

Tinti and Noffe observed that the combination of the cyano analogue of suosan with the elements of asparatame yields superaspartame which has a potency 14 (KX) times that of sucrose (aspartame has a potency of about 180 times that of sucrose. Fig. 39.19). Subsequently, these authors discovered sweet guanidines such as the compound SC-45647 which has a potency 28000 times that of sucrose. More recently, they reported iV-alkyl-substi-tuted aspartame derivatives such as neotame which has a potency 10 000 times that of sucrose. For these three high-potency sweeteners, Walters et al. were able to identify a five-point pharmacophore model in which the carboxylate, the two hydrophobic groups and two NH groups match well... 

Neotame is an artificial sweetener derived from and similar in structure to aspartame. However, neotame is heat stable, much more potent and of no danger to those suffering from phenylketonuria, as it is not metabolised into phenylalanine. Peptidases, which would typically break the peptide bond between the aspartic acid and phenylalanine moieties, are essentially blocked by the presence of the... 

Aspartame is the market leader among artificial sweeteners. It is a methyl ester of a dipeptide, unrelated to any carbohydrate. A recently approved relative, Neotame, is even sweeter than aspartame. 

RPLC with MS detection was used for the analysis of seven artificial sweeteners (aspartame, saccharin, acesulfame-K, neotame, sucralose, cyclamate, and alitame) and one natural sweetener (stevioside). Samples were extracted using methanokwater and injected without any cleanup into the LC—MS system. Separation is carried out using a Cis column and gradient elution. Sweeteners were quantified using selective-ionization recording (SIR) at m/z 178, 397, 377, 293, 641, 312, 162, and 182 for cyclamate, sucralose, neotame, aspartame, stevioside, alitame, acesulfame-K, and saccharin, respectively, with a warfarin sodium m/z = 307) used as an internal standard [24]. For a detailed discussion of other analytical methods to determine artificial sweeteners, refer to [25]. 

Neotame, JV-(N-(3,3-dimethylbutyl)-L-a-aspartyl)-L-phenylala-nine 1-methyl ester (11-32), is another sweetener from the... 

Neotame (brand name n/a) was approved in 2002 by the FDA as a general purpose sweetener, which is approximately 7000 times sweeter than sugar. 

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