Saccharin, structure

Saccharin was discovered at Johns Hopkins Uni versity in 1879 in the course of research on coal tar derivatives and is the oldest artificial sweetener In spite of Its name which comes from the Latin word for sugar saccharin bears no structural relationship to any sugar Nor is saccharin itself very soluble in wa ter The proton bonded to nitrogen however is fairly acidic and saccharin is normally marketed as its water soluble sodium or calcium salt Its earliest applications were not in weight control but as a... 

Saccharin sucralose and aspartame illustrate the diversity of structural types that taste sweet and the vitality and continuing development of the in dustry of which they are a part ... 

Examine the structures oisucrose, the natural sweetener, and saccharin, sodium cyclamate and aspartame (Nutrasweet), three of the most common artificial sweeteners. What, if any, structural features do these molecules have in common Compare electrostatic potential maps for the different sweeteners. Are there any significant features in common Based on yom findings, do you think it is likely that entirely different artifical sweeteners might be discovered Explain. 

Structure 51 has been assigned to saccharin on the basis of infrared spectral data. ... 

Surprisingly, the bromination of ergoline structures with N-bromosaccharin yielded as the main product the ergoline derivatives with a saccharin on the position 2 instead of the expected 2-bromo-derivatives ... 

Hi) Sulfamates.—The two most well known sweet compounds in this class are cyclamate (9) and saccharin (10). Considerable structural modifications have been recorded, and their tastes ascertained. 

Structurally related to saccharin are the oxathiazinone dioxides (104). Clauss and coworkers synthesized a series of these compounds, and demonstrated that they possess intense sweetness. Acesulfame-K, the potassium salt of 3,4-dihydro-6-methyl-l,2,3-oxathiazin-4-one 2,2-dioxide (104) has a sweetness intensity 130 times that of sucrose. 

A few stable gold(III) imidate complexes have been authenticated by X-ray structure determinations. Most of the claimed gold(III) imidate complexes including those containing succinimide, phthalimide, saccharin or N-methylidantoin derivatives [40] were subsequently reformulated as gold(I) species [41[. 

FIG. 25 Chemical structures of (a) erythritol, (b) sodium saccharin, and (c) aspartame. 

Relatively high molecular weight is a feature of the chemotype exemplified by 4-11 and this can require creative formulation techniques. Pharmacokinetic properties of a lead candidate (structure unknown) from the same series that provided 10 were inadequate to provide sufficient exposures at high doses to support preclinical safety studies. However, cocrystal formulations with saccharin or gentisic acid improved water solubility by 50-fold and increased oral exposures up to 10-fold relative to traditional formulations at 20mg/kg [64]. 

Matzke technique, 72 10 Maule color reaction, 75 7 Maumee saccharin process, 24 235 Mauritius hemp, 77 296 Mavik, molecular formula and structure, 5 151t... 

The saccharinic acids formed from hexoses have been especially examined because of the relationships of the a and /8 isomers (C-2 epi-mers). Structures of saccharinic acids derived from D-glucose are glu-cometasaccharinic acid (51), glucoisosaccharinic acid (52), and glucosaccharinic acid (53). The a- and /3- isomers of metasaccharinic acid can reversibly isomerize when exposed to base because of the labile proton at C-2. 

The (branched) amylopectin is generally considered more alkali-stable than amylose. Amylopectin produced a very small proportion of glucoiso-saccharinic acid after exposure to M KOH at 25° for nearly 2 months."" However, glycogen, which has a similar structure, but more a-D-(1 6) bonding, undergoes the peeling process where a-o-(1 4) bonds are pre-... 

Fibrous structures represent a grain refinement of columnar structure. Stress-relieving additives, eg, saccharin or coumarin, promote such refinement, as do high deposition rates. These may be considered intermediate in properties between columnar and fine-grained structures. 

Sweet Taste. The mechanism of sweetness perception has been extensively studied because of its commercial importance. Many substances that vary in chemical structure have been discovered which are similar to the taste of sucrose. Commercial sweeteners include sucralose, acesulfame-K, saccharin, aspartame, cyclamate (Canada) and the protein thaumatin 4), Each sweetener is unique in its perceived sensation because of the time to the onset of sweetness and to maximum sweetness, ability to mask other sensations, persistence, aftertaste and intensity relative to sucrose [TABLE IT. For example, the saccharides, sorbitol and... 

Problem 16.61 Write structures for compounds (A) through (C) in the synthesis of saccharin. 

Acesulfame-K. Acesulfame-K [55589-62-3] (4), the potassium salt of acesulfame [33665-90-6] (6-methyl-l,2,3-oxathiazin-4(3Ff)-one 2,2-dioxide), is a sweetener that resembles saccharin in structure and taste profile. 5,6-Dimethyl-l,2,3-oxathiazine-4(3 H)-one 2,2-dioxide, the first of many sweet compounds belonging to the dihydrooxathiazinone dioxide class, was discovered accidentally in 1967 (63). From these many sweet compounds, acesulfame was chosen for commercialization. To improve water solubility, the potassium salt was made. Acesulfame-K (trade name Sunette) was approved for dry product use in the United States in 1988 and in Canada in October, 1994. Later, it was approved by the FDA for additional food categories such as yogurts, frozen and refrigerated desserts, and baked goods. 

---