Tagatose

Last updated
Tagatose
Tagatose.png
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 OOjs UI icon edit-ltr-progressive.svg
E number E963 (glazing agents, ...)
PubChem CID
UNII
  • InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6-/m1/s1 X mark.svgN
    Key: BJHIKXHVCXFQLS-PQLUHFTBSA-N X mark.svgN
  • InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6-/m1/s1
    Key: BJHIKXHVCXFQLS-PQLUHFTBBT
  • OC[C@@H](O)[C@H](O)[C@H](O)C(CO)=O
Properties
C6H12O6
Molar mass 180.16 g/mol
AppearanceWhite solid
Melting point 133 to 135 °C (271 to 275 °F; 406 to 408 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
0
0
Safety data sheet (SDS)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Tagatose is a hexose monosaccharide. It is 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

Contents

Production

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 contents 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. 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]

Characteristics

Functional characteristics

Low glycemic index

Tagatose has very similar sweetness to sugar while its glycemic index (GI 3) is very low. GI is a measure of the effects of carbohydrates in food on blood sugar levels. It estimates how much each gram of available carbohydrate (total carbohydrate minus fiber) in a food raises a person's blood 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 other sweeteners.

High blood glucose levels or repeated glycemic "spikes" following a meal may promote type 2 diabetes by increasing systemic glycative stress other oxidative stress to the vasculature and also by the direct increase in insulin 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-related macular degeneration than others. [12]

Antihyperglycemic effect

The Korea Food & Drug Administration approved the safety and function of tagatose for controlling postprandial blood glucose level. Tagatose reduces blood glucose level in the liver by promoting glucokinase activity which promotes transfer of glucose to glycogen. It also inhibits digestive enzymes and degradation of carbohydrates in small intestine which result in inhibition of carbohydrate absorption in the body. Antihyperglycemic function is important for those with both type 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]

Physical characteristics

Tagatose is a white crystalline powder with a molecular formula of C6H12O6 with a molecular weight of 180.16 g/mol. Active maillard reaction of tagatose enhances flavor and brown coloring performance and is usually used for baking, cooking and with high-intensity sweeteners to mask their bitter aftertaste.

Marketing

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 from whey for D-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 the Benelux 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 that PepsiCo and Yoplait 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 for D-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]

Related Research Articles

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A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 and thus with the empirical formula Cm(H2O)n, which does not mean the H has covalent bonds with O. However, not all carbohydrates conform to this precise stoichiometric definition, nor are all chemicals that do conform to this definition automatically classified as carbohydrates.

<span class="mw-page-title-main">Sucralose</span> Non-nutritive sweetener

Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds very little food energy. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose, 3 times as sweet as both aspartame and acesulfame potassium, and 2 times as sweet as sodium saccharin.

<span class="mw-page-title-main">Splenda</span> Brand of sugar substitute

Splenda is a global brand of sugar substitutes and reduced-calorie food products. While the company is known for its original formulation containing sucralose, it also manufactures items using natural sweeteners such as stevia, monk fruit and allulose. It is owned by the American company Heartland Food Products Group. The high-intensity sweetener ingredient sucralose used in Splenda Original is manufactured by the British company Tate & Lyle.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

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5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote it being a sugar alcohol.

<span class="mw-page-title-main">Glycemic index</span> Number assigned to food

The glycemic (glycaemic) index is a number from 0 to 100 assigned to a food, with pure glucose arbitrarily given the value of 100, which represents the relative rise in the blood glucose level two hours after consuming that food. The GI of a specific food depends primarily on the quantity and type of carbohydrate it contains, but is also affected by the amount of entrapment of the carbohydrate molecules within the food, the fat and protein content of the food, the amount of organic acids in the food, and whether it is cooked and, if so, how it is cooked. GI tables, which list many types of foods and their GIs, are available. A food is considered to have a low GI if it is 55 or less; high GI if 70 or more; and mid-range GI if 56 to 69.

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H
10
O
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References

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  13. WHO report, 13Nov 2009
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  17. "Enforcement Reports".