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    Tagatose

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    Xls

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

    2D Structure

    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.