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Chemistry

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Also known as: 87-81-0, D-lyxo-hexulose, Lyxo-2-hexulose, 17598-81-1, Tagatose, d-, Naturlose
Molecular Formula
C6H12O6
Molecular Weight
180.16  g/mol
InChI Key
BJHIKXHVCXFQLS-PQLUHFTBSA-N
FDA UNII
T7A20Y888Y

Tagatose
tagatose is a natural product found in Pogostemon cablin and Solanum lycopersicum with data available.
1 2D Structure

Tagatose

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
2.1.2 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
2.1.3 InChI Key
BJHIKXHVCXFQLS-PQLUHFTBSA-N
2.1.4 Canonical SMILES
C(C(C(C(C(=O)CO)O)O)O)O
2.1.5 Isomeric SMILES
C([C@H]([C@@H]([C@@H](C(=O)CO)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
T7A20Y888Y
2.3 Synonyms
2.3.1 MeSH Synonyms

1. D-tagatose

2. Tagatose

3. Tagatose, (alpha-d)-isomer

4. Tagatose, (beta-d)-isomer

5. Tagatose, (d)-isomer

6. Tagatose, (dl)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 87-81-0

2. D-lyxo-hexulose

3. Lyxo-2-hexulose

4. 17598-81-1

5. Tagatose, D-

6. Naturlose

7. Keto-d-tagatose

8. Tagatose [nf]

9. Chebi:47693

10. T7a20y888y

11. Tagatose (nf)

12. Rel-(3s,4s,5r)-1,3,4,5,6-pentahydroxyhexan-2-one

13. Dl-tagatose

14. Einecs 201-772-3

15. Unii-t7a20y888y

16. Mfcd00134449

17. D-tagatose [mi]

18. D-tagatose [fcc]

19. Tagatose [mart.]

20. Tagatose [usp-rs]

21. Schembl4035

22. Tagatose, D- [ii]

23. Chembl1236183

24. Zinc2516866

25. D-(-)-tagatose, >=98.5%

26. S5387

27. D-(-)-tagatose, Analytical Standard

28. Akos015856492

29. Akos015902493

30. Ccg-266424

31. Db04936

32. Ncgc00248704-01

33. As-44378

34. Hy-42680

35. Cs-0028435

36. T1501

37. D09007

38. Wurcs=2.0/1,1,0/[ho112h]/1/

39. 134t449

40. Q414089

41. W-200517

42. Tagatose, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C6H12O6
XLogP3-3.2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass180.06338810 g/mol
Monoisotopic Mass180.06338810 g/mol
Topological Polar Surface Area118 Ų
Heavy Atom Count12
Formal Charge0
Complexity147
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Intended for use as a therapeutic adjunct in the treatment of type II diabetes.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Oral tagatose significantly blunts the rise in plasma glucose seen after oral glucose in patients with diabetes mellitus in a dose-dependent manner without significantly affecting insulin levels. The minimal elevation of plasma tagatose levels in normal patients and the adverse gastrointestinal effects seen following larger doses of tagatose support poor absorption of this hexose and suggest that tagatose may act by attenuating glucose absorption in the intestine.


5.2 MeSH Pharmacological Classification

Iron Chelating Agents

Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems. (See all compounds classified as Iron Chelating Agents.)


5.3 Absorption, Distribution and Excretion

Absorption

Only 15-20 percent of tagatose is absorbed in the small intestine.


5.4 Metabolism/Metabolites

Tagatose does not influence the level of blood glucose nor insulin levels.


5.5 Mechanism of Action

he steps in the metabolism of tagatose are identical to those for fructose or fruit sugar but tagatose is incompletely absorbed. Only 15-20 percent of tagatose is absorbed in the small intestine. The major part of ingested tagatose is fermented in the colon by indigenous microflora, resulting in the production of short-chain fatty acids. The short chain fatty acids are absorbed almost completely and metabolized.


API Reference Price

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17-Dec-2021
17-Dec-2021
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