D-Tagatose

Описание

D-tagatose is a carbohydrate occurring in small amounts in several foods. The solubility in water is approximately 580 g/L at room temperature. As a ketohexose, tagatose reacts in foods in browning reactions like other ketohexoses, for example, fructose.
Tagatose is, depending on the concentration, approximately 92 % as sweet as sucrose and noncariogenic. The caloric value of tagatose is generally set to 1.5 kcal/g.
In the European Union, tagatose is approved as a novel food. In the United States, tagatose has GRAS status and it is also approved in many other countries.

Химические свойства

white to off-white crystalline powder

Использование

D-tagatose is a compound useful in organic synthesis.

Методы производства

Tagatose is obtained from D-galactose by isomerization under alkaline conditions in the presence of calcium.

Фармацевтические приложения

Tagatose is used as a sweetening agent in beverages, foods, and pharmaceutical applications. A 10% solution of tagatose is about 92% as sweet as a 10% sucrose solution. It is a low-calorie sugar with approximately 38% of the calories of sucrose per gram. It occurs naturally in low levels in milk products. Like other sugars (fructose, glucose, sucrose), it is also used as a bulk sweetener, humectant, texturizer, and stabilizer, and may be used in dietetic foods with a low glycemic index.

Биологическая активность

D-Tagatose, a ketohexose acts as a low-calorie functional sweetener. Tagatose can be used as a preservative in cosmetic, detergent and pharmaceutical formulations.Tagatose is also used in diet soft drinks, chewing gum, frozen yogurt and non-fat ice cream.
Potential sugar substitute rarely found in nature. Produced using a biotransformation method with L-arabinose isomerase as the biocatalyst and D-galactose as the substrate.

Побочные эффекты

Some human trials of D-tagatose have found that doses of 30 grams or more cause gastrointestinal side effects like flatulence, diarrhea, nausea, and vomiting.
However, only a minority of people appear to be affected, and mostly only with light to moderate symptom severity.
The GI side effects of D-tagatose seem to be unpleasant but harmless. They’re may be due to osmotic (water-retaining) effects of high D-tagatose doses moving through your intestines.
D-tagatose may interact with some prescription drugs, especially blood sugar lowering drugs, and could cause hypoglycemia (dangerously low blood sugar levels).
And in people with diabetes or a history of kidney stones, temporary rises in uric acid blood levels caused by high dose D-tagatose may be an issue.

Безопасность

Tagatose is safe for use in food and beverages. It has been used in pharmaceutical products.

хранилище

Tagatose is stable under pH conditions typically encountered in foods (pH>3). It is a reducing sugar and undergoes the Maillard reaction.
Tagatose is stable under typical storage conditions. It caramelizes at elevated temperature.

Методы очистки

Crystallise D(-)-tagatose from EtOH/H2O (6:1). It mutarotates from [] 22D +2o (2minutes) to –5.0o (30minutes) (c 4, H2O). The phenylosazone crystallises from aqueous EtOH with m 185-187o(dec), and [] 23D +47o (c 0.82, 2-methoxyethanol). [Totton & Lardy J Am Chem Soc 71 3076 1949, Gorin et al. Canad J Chem 33 1116 1955, Reichestein & Bossard Helv Chem Acta 17 753 1934, Wolfrom & Bennett J Org Chem 30 1284 1965, Beilstein 1 IV 4414.] In D2O at 27o 1H NMR showed the following ratios: -pyranose (79), -pyranose (16), -furanose (1) and -furanose (4) [Angyal Adv Carbohydr Chem 42 15 1984, Angyal & Pickles Aust J Chem 25 1711 1972].

Несовместимости

A Maillard-type condensation reaction is likely to occur between tagatose and compounds with a primary amine group to form brown or yellow-brown colored Amidori compounds. Reducing sugars will also interact with secondary amines to form an imine, but without any accompanying yellow-brown discoloration.

Регуляторный статус

GRAS listed. Included in the FDA Inactive Ingredients Database (oral and rectal solutions).