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Chemistry

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Also known as: Epicatechin, 490-46-0, L-epicatechin, (-)-epicatechol, Epicatechol, L-acacatechin

Molecular Formula

C₁₅H₁₄O₆

Molecular Weight

290.27 g/mol

InChI Key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

FDA UNII

34PHS7TU43

An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.

1 2D Structure

Epicatechol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol

2.1.2 InChI

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1

2.1.3 InChI Key

PFTAWBLQPZVEMU-UKRRQHHQSA-N

2.1.4 Canonical SMILES

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

2.2 Other Identifiers

2.2.1 UNII

34PHS7TU43

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-catechin

2. (+)-cyanidanol

3. (+)-cyanidanol-3

4. (2r,3r)-2-(3,4-dihydroxyphenyl)-3,5,7-chromanetriol

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

6. 3,3',4',5,7-flavanpentol

7. Catechin

8. Catechinic Acid

9. Catechuic Acid

10. Catergen

11. Cianidanol

12. Cyanidanol 3

13. Cyanidanol-3

14. Epicatechin

15. Kb 53

16. Kb-53

17. Kb53

18. Z 7300

19. Zyma

2.3.2 Depositor-Supplied Synonyms

1. Epicatechin

2. 490-46-0

3. L-epicatechin

4. (-)-epicatechol

5. Epicatechol

6. L-acacatechin

7. (2r,3r)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol

8. Epi-catechin

9. Epi-catechol

10. (-)epicatechin

11. (2r,3r)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-chromene-3,5,7-triol

12. L-epicatechol

13. (-)-epi Catechin

14. (2r,3r)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

15. Chebi:90

16. Epicatechol, (-)-

17. (2r,3r)-(-)-epicatechin

18. (-)-(2r:3r)-5,7,3',4'-tetrahydroxyflavan-3-ol

19. 34phs7tu43

20. Nsc81161

21. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r,3r)-

22. Nsc-81161

23. (-)-cis-epicatechin

24. Nsc 81161

25. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r-cis)-

26. Dsstox_cid_25133

27. Dsstox_rid_80694

28. Dsstox_gsid_45133

29. (2r,3r)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol

30. Epicatechin-(-)

31. Cas-490-46-0

32. Smr000156230

33. Ccris 7097

34. Einecs 207-710-1

35. Unii-34phs7tu43

36. Acacatechin

37. Colatein

38. Alpha-catechin

39. Kakaol

40. Teacatechin I

41. .alpha. Catechin

42. Ncgc00015215-02

43. 28e

44. 7295-85-4

45. L(-)-epicatechin

46. Prestwick_203

47. 2,3-cis-epicatechin

48. L-epicatechin ,(s)

49. Spectrum_000159

50. Specplus_000267

51. 2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene

52. Spectrum2_000675

53. Spectrum3_000243

54. Spectrum4_000949

55. Spectrum5_000929

56. Lopac-c-1251

57. Oprea1_209947

58. Schembl19412

59. Bspbio_001626

60. Kbiogr_001538

61. Kbioss_000639

62. Spectrum210206

63. Cid_72276

64. Mls001304012

65. Mls001304152

66. Divk1c_006363

67. Spbio_000769

68. Chembl583912

69. L-epicatechin [who-dd]

70. Dtxsid4045133

71. Acon1_001106

72. Bcbcmap01_000224

73. Bdbm23417

74. Kbio1_001307

75. Kbio2_000639

76. Kbio2_003207

77. Kbio2_005775

78. Kbio3_001126

79. Hms1923m05

80. Kuc104404n

81. Zinc119988

82. (-)-epicatechin [usp-rs]

83. Hy-n0001

84. Tox21_110101

85. 3,3',4',5,7-pentahydroxyflavane

86. Ccg-38571

87. Lmpk12020003

88. Mfcd00075648

89. S4723

90. (-)-epicatechin, Analytical Standard

91. Akos015895981

92. Tox21_110101_1

93. (-)-epicatechin, >=90% (hplc)

94. Cs-3760

95. Db12039

96. Ds-3358

97. Ksc-10-144

98. Sdccgmls-0066927.p001

99. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2r,3r)-

100. Smp1_000115

101. Ncgc00015215-01

102. Ncgc00016415-01

103. Ncgc00016415-02

104. Ncgc00016415-03

105. Ncgc00016415-04

106. Ncgc00017331-08

107. Ac-14586

108. Bp-30203

109. Cas-154-23-4

110. Cas-7295-85-4

111. B4964

112. E1226

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

114. (-)-epicatechin 1000 Microg/ml In Acetone

115. A12043

116. C09727

117. O10053

118. (-)-epicatechin 1000 Microg/ml In Acetonitrile

119. 490e460

120. A871843

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

122. Q-200001

123. Cf3ba0c2-de1b-44ab-a4d3-800f017221ba

124. Epicatechin, Primary Pharmaceutical Reference Standard

125. Q23050136

126. (-)-epicatechin (constituent Of Maritime Pine) [dsc]

127. (-)-epicatechin (constituent Of Grape Seeds Oligomeric Proanthocyanidins) [dsc]

128. (-)-epicatechin(eg) (constituent Of Powdered Decaffeinated Green Tea Extract) [dsc]

129. 2-(3,4-dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene;l-epicatechin

130. (-)-cis-3,3',4',5,7-pentahydroxyflavane, (2r,3r)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1(2h)-benzopyran-3,5,7-triol

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₄O₆
Molecular Weight	290.27 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	1
Exact Mass	290.07903816 g/mol
Monoisotopic Mass	290.07903816 g/mol
Topological Polar Surface Area	110 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	364
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