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Chemistry

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Also known as: (+)-catechin, Catechin, 154-23-4, Catechuic acid, Catechinic acid, Cyanidanol

Molecular Formula

C₁₅H₁₄O₆

Molecular Weight

290.27 g/mol

InChI Key

PFTAWBLQPZVEMU-DZGCQCFKSA-N

FDA UNII

5J4Y243W61

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

1 2D Structure

Cianidanol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,3S)-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+/m0/s1

2.1.3 InChI Key

PFTAWBLQPZVEMU-DZGCQCFKSA-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

5J4Y243W61

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-catechin

2. (+)-cyanidanol

3. (+)-cyanidanol-3

4. (-)-epicatechin

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

6. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r-cis)-

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

8. Catechin

9. Catechinic Acid

10. Catechuic Acid

11. Catergen

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. (+)-catechin

2. Catechin

3. 154-23-4

4. Catechuic Acid

5. Catechinic Acid

6. Cyanidanol

7. D-catechin

8. Catergen

9. Cianidol

10. (+)-catechol

11. (+)-cyanidanol

12. Biocatechin

13. (+)-cyanidan-3-ol

14. D-catechol

15. D-(+)-catechin

16. Dexcyanidanol

17. (+)-catechin Hydrate

18. Catechin (flavan)

19. Catechol (flavan)

20. (2r,3s)-catechin

21. (2r,3s)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol

22. 3-cyanidanol, (+)-

23. Dl-catechin

24. (2r,3s)-(+)-catechin

25. Cianidanolum

26. Dl-catechol

27. (+)-cianidanol

28. 3,3',4',5,7-flavanpentol

29. Kb-53

30. (+)-cyanidanol-3

31. 7295-85-4

32. Ccris 6855

33. (+)-3',4',5,7-tetrahydroxy-2,3-trans-flavan-3-ol

34. (2r,3s)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol

35. (2r,3s)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-chromene-3,5,7-triol

36. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r-trans)-

37. Nsc 2819

38. Nsc-2819

39. Catechin, D-

40. Catechol (+)

41. Chebi:15600

42. Ai3-22757

43. Nsc2819

44. (+)-(2r,3s)-5,7,3',4'-tetrahydroxyflavan-3-ol

45. Catechin, D

46. Catechin-(+,-) Hydrate

47. (2r,3s)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

48. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r,3s)-

49. 8r1v1stn48

50. Chembl311498

51. (2r-trans)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

52. 5j4y243w61

53. 100786-01-4

54. 225937-10-0

55. Catechu

56. Gambier

57. Transepar

58. Katha

59. Trans-(+)-3,3',4',5,7-flavanpentol

60. Zyma

61. Cyanidanol-3

62. (+)-cyanidol-3

63. Cutch (dye)

64. (+)-(2r:3s)-5,7,3',4'-tetrahydroxyflavan-3-ol

65. Epicatechin-(-)

66. Cianidanol [inn:jan]

67. Mls001056745

68. Cianidanolum [inn-latin]

69. Catechine Dl-form

70. (+-)-catechin

71. 2,3-trans-catechin

72. 2,3-dihydro-4-desoxoquercetin

73. Kb 53

74. Sr-01000075742

75. Smr000326724

76. Einecs 205-825-1

77. Unii-8r1v1stn48

78. Catechinate

79. Catechuate

80. Drenoliver

81. Rac-catechin

82. (2r,3s)-3,3',4',5,7-flavanpentol

83. Tanningenic Acid

84. Dl-catechine

85. Unii-5j4y243w61

86. Z 7300

87. Procyanidin Polymer

88. Teafuran 30a

89. Kxn

90. Prestwick_998

91. Sunkatol No. 1

92. Einecs 230-731-2

93. (+/-)-catechol

94. 2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol

95. Racemic Catechin

96. Spectrum_000395

97. (+)-catechin,(s)

98. 2-(3,4-dihydroxyphenyl)-3,5,7-chromanetriol #

99. Catechin [mi]

100. Catechin, Dl-

101. Catechin [vandf]

102. Cianidanol [inn]

103. Cianidanol [jan]

104. Prestwick0_000642

105. Prestwick0_000817

106. Prestwick1_000642

107. Prestwick1_000817

108. Prestwick2_000642

109. Prestwick2_000817

110. Prestwick3_000642

111. Spectrum2_000167

112. Spectrum3_000242

113. Spectrum4_001763

114. Spectrum5_000345

115. Epitope Id:116872

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

117. Cianidanol [mart.]

118. Cianidanol [who-dd]

119. Lopac0_000219

120. Schembl19741

121. Bspbio_000643

122. Bspbio_001624

123. Kbiogr_002245

124. Kbioss_000875

125. Bidd:er0378

126. Divk1c_000647

127. (+)-2-(3,4-dihydroxyphenyl)-3,5,7-chromantriol

128. Spbio_000033

129. Spbio_002564

130. Spbio_002634

131. Catechin Dl-form [mi]

132. Bpbio1_000709

133. Cid_107957

134. (3s,2r)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol

135. Catechol, (+/-)-

136. Dtxsid3022322

137. Acon1_001489

138. Bdbm23416

139. Bdbm60836

140. Cianidanol, (+/-)-

141. Hms502a09

142. Kbio1_000647

143. Kbio2_000875

144. Kbio2_003443

145. Kbio2_006011

146. Kbio3_001124

147. Yk-85 Light Yellow Powder 85

148. (+)-catechin [usp-rs]

149. 4c94

150. Ninds_000647

151. Dtxsid001349029

152. Hms1570a05

153. Hms1570d15

154. Hms2097a05

155. Hms3260l19

156. Pharmakon1600-00210205

157. Zinc119983

158. (+)-catechin, Analytical Standard

159. Hy-n0898

160. Tnp00270

161. Tox21_500219

162. Ccg-40007

163. Lmpk12020001

164. Nsc755824

165. S3974

166. S4722

167. Stl570276

168. Trans3,3,4,5,7 Pentahydroxyflavane

169. Akos015960546

170. Cs-3759

171. Db14086

172. Lp00219

173. Nd-0342

174. Nsc-755824

175. Sdccgmls-0066526.p001

176. Sdccgsbi-0050207.p004

177. Idi1_000647

178. Ncgc00017331-01

179. Ncgc00017331-02

180. Ncgc00017331-03

181. Ncgc00017331-04

182. Ncgc00017331-05

183. Ncgc00017331-19

184. Ncgc00093689-01

185. Ncgc00093689-02

186. Ncgc00093689-03

187. Ncgc00260904-01

188. Ac-11608

189. Ac-35859

190. As-72772

191. Nci60_002303

192. (+)-catechin 1000 Microg/ml In Acetone

193. Sbi-0050207.p003

194. Eu-0100219

195. ( Inverted Exclamation Marka)-catechin Hydrate

196. (+)-catechin 1000 Microg/ml In Acetonitrile

197. C 1251

198. C06562

199. D95105

200. H10916

201. Ab00051886_13

202. (+/-)-catechin 1000 Microg/ml In Acetonitrile

203. 154c234

204. A809512

205. A878497

206. Natural Brown 3 (cutch Extra Or Gambier)

207. Q415007

208. Q-100183

209. Sr-01000075742-1

210. Sr-01000075742-7

211. Sr-01000075742-8

212. Sr-01000075742-9

213. Brd-k58736316-001-07-9

214. Brd-k58736316-001-08-7

215. Sr-01000075742-10

216. Sr-01000075742-12

217. Sr-01000075742-14

218. (+)-catechin (constituent Of Maritime Pine) [dsc]

219. D4a04a57-7609-451f-a446-53f4dfad15f5

220. (2r,3s)-2-(3,4-dihydroxyphenyl)chroman-3,5,7-triol;hydrate

221. (+)-catechin, United States Pharmacopeia (usp) Reference Standard

222. (2r,3s)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1h-chromene-3,5,7-triol

223. (+)-catechin (constituent Of Grape Seeds Oligomeric Proanthocyanidins) [dsc]

224. (+)-catechin (constituent Of Powdered Decaffeinated Green Tea Extract) [dsc]

225. (+)-catechin, Pharmaceutical Secondary Standard; Certified Reference Material

226. (2r,3s)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol;hydrate

227. (2r,3s)-2-[3,4-bis(oxidanyl)phenyl]-3,4-dihydro-2h-chromene-3,5,7-triol;hydrate

228. (2r-trans)-2-(3,4-dihydroxyphenyl)-3-4-dihydro-2h-1-benzopyran-3,5,7-triol

229. 2-(3,4-dihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol, (2r-trans)

230. 2h-1-benzopyran-3,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r-trans)-

231. 2h-1-benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2s,3r)-rel-

232. 321-01-7

2.4 Create Date

2004-09-16

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

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( -)-Catechin

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