Tagatose

Tagatose

Names
IUPAC name (3S,4S,5R)-1,3,4,5,6-Pentahydroxy-hexan-2-one
Identifiers
CAS Number	17598-81-1 Y
3D model (Jmol)	Interactive image
ChemSpider	83142 N
PubChem	92092
InChI 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 N Key: BJHIKXHVCXFQLS-PQLUHFTBSA-N N 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
SMILES OC[C@@H](O)[C@H](O)[C@H](O)C(CO)=O
Properties
Chemical formula	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
Safety data sheet	[1]
NFPA 704	0 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Tagatose is a functional sweetener. It is a naturally occurring monosaccharide, specifically a hexose. It is often found in dairy products, and is very similar in texture to sucrose (table sugar) and is 92% as sweet, but with only 38% of the calories.

Tagatose is generally recognized as safe (GRAS) by the FAO/WHO 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.

Tagatose is a natural sweetener present in only small amounts in fruits, cacao, and dairy products. Tagatose can be commercially produced from galactose through an enzymatic process, starting with lactose which is hydrolyzed to glucose and galactose. The galactose is isomerized under alkaline conditions to D-tagatose by calcium hydroxide. The resulting mixture can then be purified and solid tagatose produced by crystallization.

D-Tagatose was proposed as a sweetener by G. Levin, after unsuccessful attempts to market L-glucose for that application. He patented an inexpensive method to make tagatose in 1988. The low food calorie contents is due to its resemblance to L-fructose.