Tagatose
From Wikipedia, the free encyclopedia
| Names | |
|---|---|
| IUPAC name
D-lyxo-Hex-2-ulose[1] | |
| Systematic IUPAC name
(3S,4S,5R)-1,3,4,5,6-Pentahydroxy-hexan-2-one | |
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.001.612 |
| E number | E963 (glazing agents, ...) |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H12O6 | |
| Molar mass | 180.16 g/mol |
| Appearance | White solid |
| Melting point | 133 to 135 °C (271 to 275 °F; 406 to 408 K) |
| Hazards | |
| NFPA 704 (fire diamond) | |
| Safety data sheet (SDS) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tagatose is a hexose monosaccharide found in small quantities in a variety of foods and has attracted attention as an alternative sweetener.[2] It is often found in dairy products, because it is formed when milk is heated. It is similar in texture and appearance to sucrose (table sugar)[3]:215 and is 92% as sweet,[3]:198 but with only 38% of the calories.[3]:209 Tagatose is generally recognized as safe by the Food and Agriculture Organization and the World Health Organization, and has been since 2001. Since it is metabolized differently from sucrose, tagatose has a minimal effect on blood glucose and insulin levels. Tagatose is also approved as a tooth-friendly ingredient for dental products. Consumption of more than about 30 grams of tagatose in a dose may cause gastric disturbance in some people, as it is mostly processed in the large intestine, similar to soluble fiber.[3]:214
Tagatose is a natural sweetener present in only small amounts in fruits, cacao, and dairy products. Starting with lactose, which is hydrolyzed to glucose and galactose, tagatose can then be produced commercially from the resulting galactose.[4] The galactose is isomerized under alkaline conditions to D-tagatose by calcium hydroxide. Under conditions employed for a Meerwein-Ponndorf-Verley reduction, the tetra-O-benzyl galactose converts to tetra-O-benzyltagatose. Hydrogenolysis removes the four benzyl groups, leaving tagatose.[5]
Tagatose also can be made from starch or maltodextrin via an enzymatic cascade reaction.[6] The process to produce tagatose powder may soon involve spray drying.[7]
Development as a sweetener
D-Tagatose was proposed as a sweetener by Gilbert Levin, after unsuccessful attempts to market L-glucose for that application. He patented an inexpensive method to make tagatose in 1988.[8] The low food calorie content is due to its resemblance to L-fructose.[9]
Safety and function
The United States Food and Drug Administration approved tagatose as a food additive in October 2003 and designated it as generally recognized as safe. The Korea Food & Drug Administration approved tagatose as health functional food for antihyperglycemic effect. The European Food Safety Authority approved tagatose as novel food and novel food ingredient. New Zealand and Australia have also approved tagatose for human consumption.[10]

