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Chemistry

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Also known as: 1257-08-5, Epicatechin gallate, (-)-epicatechin-3-o-gallate, (-)-epicatechingallate, (-)-epicatechin-3-gallate, L-epicatechin gallate

Molecular Formula

C₂₂H₁₈O₁₀

Molecular Weight

442.4 g/mol

InChI Key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

FDA UNII

92587OVD8Z

epicatechin gallate is a natural product found in Scurrula atropurpurea, Acacia omalophylla, and other organisms with data available.

1 2D Structure

(-)-Epicatechin Gallate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

2.1.2 InChI

InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1

2.1.3 InChI Key

LSHVYAFMTMFKBA-TZIWHRDSSA-N

2.1.4 Canonical SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

2.2 Other Identifiers

2.2.1 UNII

92587OVD8Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Epicatechin Gallate

2. Epicatechin Gallate, (2r-cis)-isomer

3. Epicatechin-3-gallate

4. Epicatechin-3-galloyl Ester

5. Epicatechin-3-o-gallate

2.3.2 Depositor-Supplied Synonyms

1. 1257-08-5

2. Epicatechin Gallate

3. (-)-epicatechin-3-o-gallate

4. (-)-epicatechingallate

5. (-)-epicatechin-3-gallate

6. L-epicatechin Gallate

7. Epicatechin Monogallate

8. Teatannin

9. (-)-epicatechin 3-o-gallate

10. Ecg

11. Epicatechol, Gallate

12. 3-o-galloylepicatechin

13. (-)-cis-3,3',4',5,7-pentahydroxyflavane 3-gallate

14. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl] 3,4,5-trihydroxybenzoate

15. 3-gallate(-)-epicatechol

16. (-)-epicatechin 3-gallate

17. Chembl36327

18. Epicatechin-3-o-gallate

19. Chebi:70255

20. 92587ovd8z

21. Epicatechin-3-galloyl Ester

22. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate

23. Benzoic Acid, 3,4,5-trihydroxy-, (2r,3r)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2h-1-benzopyran-3-yl Ester

24. Epicatechin 3-gallate

25. Epi-catechin 3-o-gallate

26. Epicatechin Gallate, (2r-cis)-isomer

27. Nsc 636594

28. Unii-92587ovd8z

29. Nsc636594

30. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl 3,4,5-trihydroxybenzoate

31. Epicatechol, 3-gallate, (-)-

32. Nsc-636594

33. Mfcd00075936

34. (-)epicatechingallate

35. Spectrum_000314

36. L-ecg

37. Specplus_000275

38. (-) Epicatechin Gallate

39. Epicatechin-gallate-(-)

40. Spectrum2_000165

41. Spectrum3_000246

42. Spectrum4_001540

43. Spectrum5_000080

44. (-)-cis-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1(2h)-benzopyran-3,5,7-triol 3-gallate

45. (?)-epicatechin 3-gallate

46. Schembl39047

47. Bspbio_001632

48. Epicatechol 3-gallate

49. Kbiogr_001980

50. Kbioss_000794

51. Spectrum210238

52. Benzoic Acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7-dihydroxy-2h-1-benzopyran-3-yl Ester, (2r-cis)-

53. Divk1c_006371

54. Epicatechingallate, L-

55. Spbio_000029

56. (-)epicatechin Gallate

57. Megxp0_000810

58. Epicatechin 3-o-gallate

59. Kbio1_001315

60. Kbio2_000794

61. Kbio2_003362

62. Kbio2_005930

63. Kbio3_001132

64. Dtxsid70925231

65. 3,4,5-trihydroxy-benzoic Acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl Ester

66. Hy-n0002

67. Zinc3978503

68. Bdbm50153015

69. Ccg-38376

70. Lmpk12020090

71. S3925

72. Akos015965216

73. Ac-6037

74. Am84365

75. Cs-3761

76. Sdccgmls-0066549.p001

77. (-)-epi Catechin-3-o-gallate

78. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate

79. Ncgc00179135-01

80. As-15722

81. E0890

82. 257e085

83. Sr-05000002675

84. Q-200002

85. Q5382492

86. Sr-05000002675-1

87. Brd-k50660797-001-01-0

88. Brd-k50660797-001-03-6

89. (-)-epicatechin Gallate, >=98% (hplc), From Green Tea

90. Epicatechin Gallate, Primary Pharmaceutical Reference Standard

91. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl] 3,4,5-trihydroxybenzoate

92. Rel-(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate

93. (-)-epicatechin-3-o-gallate (constituent Of Grape Seeds Oligomeric Proanthocyanidins) [dsc]

94. (-)-epicatechin-3-o-gallate(egc) (constituent Of Powdered Decaffeinated Green Tea Extract) [dsc]

95. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

96. 3,4,5-trihydroxy-benzoic Acid (2r,3r)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl Ester

97. Benzoic Acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7- Dihydroxy-2h-1-benzopyran-3-yl Ester, (-)-cis-

98. Ncgc00179135-03![(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl] 3,4,5-trihydroxybenzoate

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₈O₁₀
Molecular Weight	442.4 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	4
Exact Mass	442.08999677 g/mol
Monoisotopic Mass	442.08999677 g/mol
Topological Polar Surface Area	177 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	649
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

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.)

Protease Inhibitors

Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

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