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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
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 Weight 442.4 g/mol
Molecular Formula C22H18O10
XLogP31.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass442.08999677 g/mol
Monoisotopic Mass442.08999677 g/mol
Topological Polar Surface Area177 Ų
Heavy Atom Count32
Formal Charge0
Complexity649
Isotope Atom Count0
Defined Atom Stereocenter Count2
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

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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