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    Hydroxytyrosol

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: 10597-60-1, 3,4-dihydroxyphenylethanol, 2-(3,4-dihydroxyphenyl)ethanol, 4-(2-hydroxyethyl)benzene-1,2-diol, Dopet, 3,4-dihydroxyphenethyl alcohol
    Molecular Formula
    C8H10O3
    Molecular Weight
    154.16  g/mol
    InChI Key
    JUUBCHWRXWPFFH-UHFFFAOYSA-N
    FDA UNII
    QEU0NE4O90
    Hydroxytyrosol is a phenolic phytochemical naturally occurring in extra virgin olive oil, with potential antioxidant, anti-inflammatory and cancer preventive activities. Although the mechanisms of action through which hydroxytyrosol exerts its effects have yet to be fully determined, this agent affects the expression of various components of the inflammatory response, possibly through the modulation of the nuclear factor-kappa B (NF-kB) pathway. The effects include the modulation of pro-inflammatory cytokines, such as the inhibition of interleukin-1alpha (IL-1a), IL-1beta, IL-6, IL-12, and tumor necrosis factor-alpha (TNF-a); increased secretion of the anti-inflammatory cytokine IL-10; inhibition of the production of certain chemokines, such as C-X-C motif chemokine ligand 10 (CXCL10/IP-10), C-C motif chemokine ligand 2 (CCL2/MCP-1), and macrophage inflammatory protein-1beta (CCL4/MIP-1b); and inhibition of the expression of the enzymes inducible nitric oxide synthase (iNOS/NOS2) and prostaglandin E2 synthase (PGES), which prevent the production of nitric oxide (NO) and prostaglandin E (PGE2), respectively. In addition, hydroxytyrosol is able to regulate the expression of other genes involved in the regulation of tumor cell proliferation, such as extracellular signal-regulated and cyclin-dependent kinases. Also, hydroxytyrosol scavenges free radicals and prevents oxidative DNA damage. This induces apoptosis and inhibits proliferation in susceptible cancer cells.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-(2-hydroxyethyl)benzene-1,2-diol
    2.1.2 InChI
    InChI=1S/C8H10O3/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,9-11H,3-4H2
    2.1.3 InChI Key
    JUUBCHWRXWPFFH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=C(C=C1CCO)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    QEU0NE4O90
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 2-(3,4-dihydroxyphenyl)ethanol

    2. 3,4-dihydroxyphenylethanol

    3. Beta-3,4-dihydroxyphenylethyl Alcohol

    4. Dopet

    2.3.2 Depositor-Supplied Synonyms

    1. 10597-60-1

    2. 3,4-dihydroxyphenylethanol

    3. 2-(3,4-dihydroxyphenyl)ethanol

    4. 4-(2-hydroxyethyl)benzene-1,2-diol

    5. Dopet

    6. 3,4-dihydroxyphenethyl Alcohol

    7. 3-hydroxytyrosol

    8. 1,2-benzenediol, 4-(2-hydroxyethyl)-

    9. 2-(3,4-dihydroxyphenyl)ethyl Alcohol

    10. 3,4-dihydroxyphenethylalcohol

    11. 4-(2-hydroxyethyl)-1,2-benzenediol

    12. Beta-3,4-dihydroxyphenylethyl Alcohol

    13. Dihydroxyphenylethanol

    14. Mfcd01320529

    15. Qeu0ne4o90

    16. Chebi:68889

    17. Unii-qeu0ne4o90

    18. Dopaol

    19. 3,4-dihydroxy-1-benzeneethanol

    20. 4-(2-hydroxy-ethyl)-benzene-1,2-diol

    21. Hydroxytyrosol [mi]

    22. Schembl44363

    23. Hydroxytyrosol [inci]

    24. 3,4-dhpea

    25. Hydroxytyrosol [who-dd]

    26. Chembl1950045

    27. Ba2774

    28. Juubchwrxwpffh-uhfffaoysa-

    29. Dtxsid70147451

    30. Ba 2774

    31. Bcp31094

    32. Hy-n0570

    33. Zinc2379217

    34. 2-(3,4-di-hydroxyphenyl)-ethanol

    35. S3826

    36. 3-hydroxytyrosol, >=98% (hplc)

    37. 3-hydroxytyrosol, Analytical Standard

    38. Akos003368868

    39. Ac-5308

    40. Ccg-266246

    41. Db12771

    42. As-10017

    43. Sy017402

    44. Db-008830

    45. Am20020163

    46. Cs-0009107

    47. D2756

    48. Ft-0600597

    49. Ft-0670206

    50. N2302

    51. 597d601

    52. A801346

    53. Q744577

    54. Q-100040

    55. Brd-k04809113-001-01-7

    56. 3,4-dihydroxyphenethyl Alcohol;3,4-dihydroxyphenyl Ethanol

    2.4 Create Date
    2005-08-08
    3 Chemical and Physical Properties
    Molecular Weight 154.16 g/mol
    Molecular Formula C8H10O3
    XLogP3-0.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count2
    Exact Mass154.062994177 g/mol
    Monoisotopic Mass154.062994177 g/mol
    Topological Polar Surface Area60.7 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity116
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Platelet Aggregation Inhibitors

    Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. (See all compounds classified as Platelet Aggregation Inhibitors.)

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

    Antioxidants

    Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)