D-Tagatose
[CAS# 87-81-0]

Identification

• Classification: Biochemical >> Carbohydrate >> Monosaccharide
• Name: D-Tagatose
• Synonyms: (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• CAS Registry Number: 87-81-0
• EC Number: 201-772-3
• SMILES: C([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Melting point: 134-135 ºC (Expl.)
• Index of Refraction: 1.574, Calc.^*
• Boiling Point: 551.7±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 301.5±26.6 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Discovory and Applicatios

D-Tagatose is a naturally occurring monosaccharide that belongs to the family of sugar substitutes known as "sweeteners." It is a rare sugar that has garnered significant attention due to its potential as a low-calorie, low-glycemic sweetener with various health benefits. The discovery and subsequent development of D-tagatose highlight its applications in food science, pharmaceuticals, and as a potential therapeutic agent for managing diabetes and obesity.

The discovery of D-tagatose dates back to the 1970s when it was first identified as a component of dairy products, although its sweetening properties were not immediately recognized. Initially, D-tagatose was known to occur naturally in small amounts in various fruits and dairy products, but it was not until later studies that its sweetening potential and physiological properties were explored. The compound is a stereoisomer of D-galactose and is produced by the enzymatic epimerization of D-galactose, a process that changes the orientation of the hydroxyl group at the C-4 position of the sugar ring.

D-tagatose is significant for its sweetening properties, which are approximately 92% as sweet as sucrose, yet it contains only about 38% of the calories of table sugar. This makes it an appealing sugar substitute for use in food and beverages, especially for individuals looking to reduce their caloric intake or those managing conditions like obesity and diabetes. Unlike many other sweeteners, D-tagatose has a minimal impact on blood glucose levels, making it a valuable alternative to traditional sugars in diabetic diets. Its low glycemic index means it does not cause significant spikes in blood sugar levels when consumed, which is critical for individuals with insulin resistance or those trying to manage their blood glucose levels.

D-tagatose is also used in the production of sugar-free and low-calorie foods, including candies, beverages, baked goods, and dairy products. It can be used alone or in combination with other sweeteners to improve the taste and texture of sugar-free products. Because it is metabolized differently from regular sugar, D-tagatose does not contribute to dental cavities, making it an attractive ingredient in oral health products such as chewing gum and toothpaste. Its use in the formulation of dental care products also contributes to its role in preventing cavities by reducing the growth of harmful bacteria in the mouth.

Another area where D-tagatose has demonstrated potential is in its use as a prebiotic. Research has shown that D-tagatose can be fermented by beneficial gut bacteria, such as Bifidobacteria and Lactobacilli. This fermentation process produces short-chain fatty acids, which play a role in maintaining gut health and supporting the immune system. As a prebiotic, D-tagatose could help improve gut flora balance, which is increasingly recognized for its importance in overall health, including digestive health, immune function, and even mental health.

D-tagatose is also being studied for its potential therapeutic effects in managing metabolic disorders. Clinical research has explored its use in controlling blood sugar and insulin levels, with promising results in the management of type 2 diabetes and obesity. As a sugar substitute, D-tagatose has been shown to help reduce caloric intake while still satisfying sweet cravings, potentially aiding in weight loss and the management of metabolic health.

In summary, D-tagatose is a naturally derived monosaccharide with notable applications as a low-calorie sweetener, prebiotic, and potential therapeutic agent. Its discovery as a sweetening agent has opened up numerous possibilities for its use in food production, healthcare, and metabolic disease management. As research into its benefits continues, D-tagatose may become an even more prominent ingredient in the quest for healthier sugar alternatives.

References

Hricovínová, Z., 2025. Celebrating 50 years of the Bílik reaction: history and present. Chemical Papers, 79, 75–83.
DOI: 10.1007/s11696-024-03825-4

Hannel, T., Link, D. & Lodder, R.A., 2008. Integrated sensing and processing–acoustic resonance spectrometry (ISP-ARS) in differentiating d-á-tagatose and other toll manufactured drugs. Journal of Pharmaceutical Innovation, 3, 152–160.
DOI: 10.1007/s12247-008-9038-y

Cheng, L., Mu, W., Zhang, T., et al., 2010. An L-arabinose isomerase from Acidothermus cellulolytics ATCC 43068: cloning, expression, purification, and characterization. Applied Microbiology and Biotechnology, 86, 1089–1097.
DOI: 10.1007/s00253-009-2322-z