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

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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

Hydroxytyrosol

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 Formula	C₈H₁₀O₃
Molecular Weight	154.16 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	154.062994177 g/mol
Monoisotopic Mass	154.062994177 g/mol
Topological Polar Surface Area	60.7 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	116
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.)

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