 | |
| 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 | |
| |
3D model (JSmol) | |
| ChemSpider |
|
| ECHA InfoCard | 100.001.612 |
| E number | E963(glazing agents, ...) |
| UNII | |
| |
| |
| 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) | [1] |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Tagatose is ahexosemonosaccharide found in small quantities in a variety of foods and has attracted attention as analternative sweetener.[2] It is often found in dairy products, because it is formed when milk is heated. It is similar in texture and appearance tosucrose (table sugar)[3]:215 and is 92% as sweet,[3]:198 but with only 38% of thecalories.[3]:209 Tagatose isgenerally recognized as safe by theFood and Agriculture Organization and theWorld Health Organization, and has been since 2001. Since it is metabolized differently from sucrose, tagatose has a minimal effect onblood glucose andinsulin levels. Tagatose is also approved as atooth-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 thelarge intestine, similar to soluble fiber.[3]:214
Tagatose is a natural sweetener present in only small amounts infruits,cacao, anddairy products. Starting withlactose, which ishydrolyzed toglucose andgalactose, tagatose can then be produced commercially from the resulting galactose.[4] The galactose isisomerized under alkaline conditions toD-tagatose bycalcium hydroxide. Under conditions employed for aMeerwein-Ponndorf-Verley reduction, the tetra-O-benzyl galactose converts to tetra-O-benzyltagatose.Hydrogenolysis removes the fourbenzyl 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 involvespray drying.[7]
D-Tagatose was proposed as a sweetener byGilbert Levin, after unsuccessful attempts to marketL-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 toL-fructose.[9]
The United StatesFood and Drug Administration approved tagatose as a food additive in October 2003 and designated it asgenerally recognized as safe. TheKorea Food & Drug Administration approved tagatose as healthfunctional food forantihyperglycemic effect. TheEuropean Food Safety Authority approved tagatose asnovel food and novel food ingredient. New Zealand and Australia have also approved tagatose for human consumption.[10]
Tagatose has very similar sweetness to sugar, while itsglycemic index (GI 3) is very low. GI is a measure of the effects ofcarbohydrates in food on blood sugar levels. It estimates how much each gram of available carbohydrate (total carbohydrate minusfiber) in a food raises a person'sblood glucose level following consumption of the food, relative to consumption of glucose. Glucose has a glycemic index of 100, by definition, and other foods have lower glycemic index.Sucrose has a GI of 68,fructose is 24, and tagatose has very low GI compared with othersweeteners.
High blood glucose levels or repeated glycemic "spikes" following a meal may promotetype 2 diabetes by increasing systemic glycative stress other oxidative stress to the vasculature and also by the direct increase ininsulin levels,[11] while individuals who followed a low-GI diet over many years were at a significantly lower risk for developing both type 2 diabetes,coronary heart disease, and age-relatedmacular degeneration than others.[12]
The Korea Food & Drug Administration approved the safety and function of tagatose for controllingpostprandial blood glucose level. Tagatose reduces blood glucose level in the liver by promotingglucokinase activity, which promotes transfer of glucose to glycogen. It also inhibits digestiveenzymes and degradation of carbohydrates in small intestine, which result in inhibition of carbohydrate absorption in the body. Antihyperglycemic function is important for those with bothtype 1 diabetes mellitus and type 2 diabetes mellitus, especially because diabetes is continuously growing and spreading to the younger generation. US$92 billion was spent for diabetes medication in 2008 in the US, and US$50 billion is paid in China per year.[13]
Tagatose is a white crystalline powder with amolecular formula of C6H12O6 with amolecular weight of 180.16 g/mol. Activemaillard reaction of tagatose enhances flavor and brown coloring performance and is usually used for baking, cooking and withhigh-intensity sweeteners to mask their bitter aftertaste.
In 1996, MD/Arla Foods acquired the rights to production from Spherix, the American license holder. In the following years, no products were brought to market by MD/Arla Foods, so Spherix brought them before a US Court of Arbitration for showing insufficient interest in bringing the product to market. The companies settled, with MD/Arla Foods agreeing to pay longer-term royalties to Spherix and Spherix agreeing to not take further action.
In March 2006, SweetGredients (a joint venture company of Arla Foods and Nordzucker AG) decided to shelve the tagatose project. SweetGredients was the only worldwide producer of tagatose. While progress had been made in creating a market for this innovative sweetener, it had not been possible to identify a large enough potential to justify continued investments, and SweetGredients decided to close down the manufacturing of tagatose in Nordstemmen, Germany.
In 2006, the Belgian company Nutrilab NV took over the Arla (SweetGredients) stocks and project, and set up an 800-tons-per-year production site in Italy with an enzymatic process fromwhey forD-tagatose with the brand name Nutrilatose. This process was said to be considerably cheaper than the chemical process previously used by Arla.[14] In 2007 Damhert N.V., the mother company of Nutrilab, released the tagatose-based sweetener Tagatesse under its own brand name, along with some other products (jams and some chocolate-based products) using tagatose[15] in theBenelux and France. Damhert's marketing strategy was to gradually build up the market for tagatose by introducing it to small and medium-sized companies. In 2013, 30% of the profits of Damhert were reported to come from tagatose, and they were preparing to scale up their production capacity to 2,500 tons per year.[14] It was also reported in February 2013 thatPepsiCo andYoplait were interested in using tagatose. Damhert were considering in the longer term building a 10,000-tons-per-annum tagatose plant in Belgium but needed to find the capital to build such a plant.[16]
One of the major producers forD-tagatose was CJ Cheiljedang, located in South Korea, under the brand name "Baeksul Tagatose". In 2011, the U.S. Food and Drug Administration approved CJ Cheiljedang's enzyme conversion tagatose production as a food additive and designated it as generally recognized as safe.[17]
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