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Chemistry

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Also known as: 3,4-dihydroxycinnamic acid, 331-39-5, Trans-caffeic acid, 501-16-6, 3,4-dihydroxybenzeneacrylic acid, 3-(3,4-dihydroxyphenyl)acrylic acid
Molecular Formula
C9H8O4
Molecular Weight
180.16  g/mol
InChI Key
QAIPRVGONGVQAS-DUXPYHPUSA-N
FDA UNII
U2S3A33KVM

Caffeic Acid
Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
1 2D Structure

Caffeic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
2.1.2 InChI
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
2.1.3 InChI Key
QAIPRVGONGVQAS-DUXPYHPUSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1C=CC(=O)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=C(C=C1/C=C/C(=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
U2S3A33KVM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 3,4-dihydroxycinnamic Acid

2. Caffeic Acid, (e)-isomer

3. Caffeic Acid, (z)-isomer

4. Caffeic Acid, Monosodium Salt

5. Cis-caffeic Acid

6. Sodium Caffeate

7. Trans-caffeic Acid

2.3.2 Depositor-Supplied Synonyms

1. 3,4-dihydroxycinnamic Acid

2. 331-39-5

3. Trans-caffeic Acid

4. 501-16-6

5. 3,4-dihydroxybenzeneacrylic Acid

6. 3-(3,4-dihydroxyphenyl)acrylic Acid

7. (e)-3-(3,4-dihydroxyphenyl)acrylic Acid

8. Cinnamic Acid, 3,4-dihydroxy-

9. (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoic Acid

10. 3-(3,4-dihydroxyphenyl)-2-propenoic Acid

11. (e)-3,4-dihydroxycinnamic Acid

12. 2-propenoic Acid, 3-(3,4-dihydroxyphenyl)-

13. Trans-caffeate

14. (e)-3-(3,4-dihydroxyphenyl)prop-2-enoic Acid

15. 4-(2-carboxyethenyl)-1,2-dihydroxybenzene

16. 3,4-dihydroxy-trans-cinnamate

17. Caffeicacid

18. 3-(3,4-dihydroxyphenyl)propenoic Acid

19. 4-(2'-carboxyvinyl)-1,2-dihydroxybenzene

20. Nsc 57197

21. Caffeate

22. 2-propenoic Acid, 3-(3,4-dihydroxyphenyl)-, (e)-

23. 3-(3,4-dihydroxy Phenyl)-2-propenoic Acid

24. Nsc-57197

25. Chembl145

26. Nsc-623438

27. U2s3a33kvm

28. Ai3-63211

29. Mls000069738

30. 71693-97-5

31. Chebi:16433

32. Trans-3,4-dihydroxycinnamic Acid

33. Nsc57197

34. 331-89-5

35. Smr000058214

36. (2e)-3-(3,4-dihydroxyphenyl)acrylic Acid

37. 2-propenoic Acid, 3-(3,4-dihydroxyphenyl)-, (2e)-

38. Mfcd00004392

39. Caffeic Acid - Natural

40. Ccris 847

41. Hsdb 7088

42. Sr-01000000203

43. Einecs 206-361-2

44. Unii-u2s3a33kvm

45. Caffeic Acid Dehydrogenation Homopolymer

46. Chebi:36281

47. Caffeic-acid

48. Caffeic Acid Pure

49. Caffeic Acid, 1

50. Caffeic Acid 1000 Microg/ml In Acetone

51. 3,4-dihydroxycinnamic Acid (caffeic Acid)

52. Caffeic Acid Polymer

53. Caffeic Acid,(s)

54. Caffeic Acid, Trans-

55. 3,4-dihydroxycinnamate

56. Caffeic Acid Natural

57. Opera_id_1700

58. Caffeic Acid [mi]

59. Caffeic Acid [dsc]

60. Cinnamic Acid,4-dihydroxy-

61. 3,4-dihydroxycinnamic Acid, Predominantly Trans

62. Caffeic Acid [hsdb]

63. Caffeic Acid [iarc]

64. Caffeic Acid [inci]

65. 3,4-dihydroxybenzeneacrylate

66. Schembl23358

67. Mls001076493

68. Mls002207132

69. Mls002222302

70. Mls006011849

71. Bidd:er0456

72. Spectrum1503987

73. Caffeic Acid [who-dd]

74. 2-propenoic Acid,3-(3,4-dihydroxyphenyl)-, (2e)-

75. 3,4-dihydroxycinnamate, Xvii

76. Bdbm4375

77. Cid_689043

78. Gtpl5155

79. 3-(3,4-dihydroxyphenyl)-2-propenoic Acid, Homopolymer

80. Zinc58172

81. 2-propenoic Acid, 3-(3,4-dihydroxyphenyl)-, Homopolymer

82. Amy3943

83. Dtxsid901316055

84. Hms2235g09

85. Hms3260j17

86. Hms3649o17

87. Bcp28271

88. Hy-n0172

89. Tox21_500208

90. Bbl012113

91. Caffeic Acid - Cas 331-39-5

92. Ccg-38895

93. Nsc623438

94. S2277

95. Stk397812

96. Caffeic Acid, >=98.0% (hplc)

97. 2-propenoic Acid,4-dihydroxyphenyl)-

98. Akos000144463

99. Ac-8006

100. Cs-8205

101. Db01880

102. Lp00208

103. Sdccgmls-0002982.p003

104. Sdccgsbi-0050196.p004

105. Ncgc00017364-04

106. Ncgc00017364-05

107. Ncgc00017364-06

108. Ncgc00017364-07

109. Ncgc00017364-08

110. Ncgc00017364-09

111. Ncgc00017364-10

112. Ncgc00017364-11

113. Ncgc00017364-12

114. Ncgc00017364-13

115. Ncgc00017364-22

116. Ncgc00022654-03

117. Ncgc00022654-04

118. Ncgc00022654-05

119. Ncgc00022654-06

120. Ncgc00022654-07

121. Ncgc00022654-08

122. Ncgc00022654-09

123. Ncgc00260893-01

124. (e)-3-(3,4-dihydroxyphenyl)acrylicacid

125. As-10895

126. Bp-30112

127. Smr004703501

128. Xc164210

129. Caffeic Acid, Purum, >=95.0% (hplc)

130. Ab00490047

131. Eu-0100208

132. N1735

133. Sw197202-3

134. 2-morpholin-4-yl-isonicotinicacidhydrochloride

135. C 0625

136. C-1500

137. C01197

138. C01481

139. (2e)-3-(3,4-dihydroxyphenyl)-2-propenoic Acid

140. 3-(3,4-dihydroxyphenyl)-2-propenoic Acid Polymer

141. 331c395

142. A851723

143. Q414116

144. Sr-01000000203-2

145. Sr-01000000203-6

146. Sr-01000000203-7

147. Sr-01000000203-8

148. Brd-k09900591-001-06-9

149. Sr-01000000203-13

150. Caffeic Acid (constituent Of Black Cohosh) [dsc]

151. F3096-1708

152. 8b3e4da7-f3b0-4972-a315-2e387071737f

153. Trans-caffeic Acid, Certified Reference Material, Tracecert(r)

154. Caffeic Acid, Matrix Substance For Maldi-ms, >=99.0% (hplc)

155. Caffeic Acid, United States Pharmacopeia (usp) Reference Standard

156. Caffeic Acid, Matrix Substance For Maldi-ms, >=99.0% (hplc), Powder, Light Beige

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 180.16 g/mol
Molecular Formula C9H8O4
XLogP31.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass180.04225873 g/mol
Monoisotopic Mass180.04225873 g/mol
Topological Polar Surface Area77.8 Ų
Heavy Atom Count13
Formal Charge0
Complexity212
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
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.)


4.2 Metabolism/Metabolites

Enzymes involved in its /caffeic acid/ metabolism have not been identified. In the following, caffeic (CA), chlorogenic (CGA), and dihydrocaffeic (DHCA) acids were incubated with hepatocytes and shown to undergo metabolism by cytochrome P450, catechol-O-methyltransferase (COMT), and beta-oxidation enzymes. Ferulic (FA) or dihydroferulic (DHFA) acids, formed as the result of CA- or DHCA-O-methylation by COMT, were also O-demethylated by CYP1A1/2 but not CYP2E1. DHCA or DHFA also underwent side chain dehydrogenation to form CA and FA, respectively, which was prevented by thioglycolic acid, an inhibitor of the beta-oxidation enzyme acyl CoA dehydrogenase. The rates of glutathione conjugate formation catalyzed by NADPH/microsomes (CYP2E1) in decreasing order DHCA>CA>CGA trend which was in reverse order to the rates of their O-methylation by COMT. The CA- and DHCA-o-quinones formed by NADPH/P450 likely inhibited COMT but can readily form glutathione conjugates. CA, DHCA and DHFA were inter-metabolized to each other and to FA by isolated rat hepatocytes whereas FA was metabolized only to CA but not to DHCA or DHFA. CA, DHCA, FA, DHFA and CGA showed a dose-dependent hepatocyte toxicity and the LD(50) (2 h), determined were in decreasing order of effectiveness DHCA>CA>DHFA>CGA>FA. In summary, evidence has been provided that O-methylation, GSH conjugation, hydrogenation and dehydrogenation are involved in the hepatic metabolism of CA and DHCA. The O-methylation pathway for CA and DHCA is a detoxification route whereas o-quinones formation catalyzed by P450 is the toxification route.

Moridani MY et al; Toxicol Letters 133(2-3): 141-151 (2002)


In rats, chlorogenic acid is hydrolysed in the stomach and intestine to caffeic and quinic acids. A number of metabolites have been identified. Glucuronides of meta-coumaric acid and meta-hydroxyhippuric acid appear to be the main metabolites in humans. After oral administration of caffeic acid to human volunteers, O-methylated derivatives (ferulic, dihydroferulic and vanillic acids) were excreted rapidly in the urine, while the meta-hydroxyphenyl derivatives appeared later. The dehydroxylation reactions were ascribed to the action of intestinal bacteria.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V56 125 (1993)


Caffeic Acid has known human metabolites that include (2S,3S,4S,5R)-6-[4-[(E)-2-carboxyethenyl]-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid and (2S,3S,4S,5R)-6-[5-[(E)-2-carboxyethenyl]-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


4.3 Mechanism of Action

Caffeic acid phenethyl ester (CAPE) was synthesized from caffeic acid and phenethyl alcohol (ratio 1:5) at room temperature with dicyclohexyl carbodiimide (DCC) as a condensing reagent. The yield was about 38%. CAPE was found to arrest the growth of human leukemia HL-60 cells. It also inhibits DNA, RNA and protein synthesis in HL-60 cells with IC50 of 1.0 M, 5.0 M and 1.5 M, respectively.

PMID:8973597 Jain-Hong C et al; Cancer Letters 108(2): 211-214 (1996)


In an attempt to understand the antihyperglycemic action of caffeic acid, the myoblast C2C12 cells were employed to investigate the glucose uptake in the present study. Caffeic acid enhanced the uptake of radioactive glucose into C2C12 cells in a concentration-dependent manner. Similar effect of phenylephrine on the uptake of radioactive glucose was also observed in C2C12 cells. Prazosin attenuated the action of caffeic acid in a way parallel to the blockade of phenylephrine. Effect of caffeic acid on alpha1-adrenoceptors was further supported by the displacement of [3H]prazosin binding in C2C12 cells. Moreover, the glucose uptake-increasing action of phenylephrine in C2C12 cells was inhibited by the antagonists of alpha1A-adrenoceptors, both tamsulosin and WB 4101, but not by the antagonist of alpha1B-adrenoceptors, chlorethylclonidine (CEC). The presence of alpha1A-adrenoceptors in C2C12 cells can thus be considered. Similar inhibition of the action of caffeic acid was also obtained in C2C12 cells co-incubating these antagonists. An activation of alpha1A-adrenoceptors seems responsible for the action of caffeic acid in C2C12 cells. In the presence of U73312, the specific inhibitor of phospholipase C, caffeic acid-stimulated uptake of radioactive glucose into C2C12 cells was reduced in a concentration-dependent manner and it was not affected by U73343, the negative control of U73312. Moreover, chelerythrine and GF 109203X diminished the action of caffeic acid at concentrations sufficient to inhibit protein kinase C. Therefore, the obtained data suggest that an activation of alpha1A-adrenoceptors in C2C12 cells by caffeic acid may increase the glucose uptake via phospholipase C-protein kinase C pathway.

PMID:10961374 Cheng J et al; Naunyn Schmiedebergs Arch Pharmacol 362(2): 122-127 (2000)


Caffeic acid (CA, 3,4-dihydroxycinnamic acid), at 2% in the diet, had been shown to be carcinogenic in forestomach and kidney of F344 rats and B6C3F1 mice. Based on its occurrence in coffee and numerous foods and using a linear interpolation for cancer incidence between dose 0 and 2%, the cancer risk in humans would be considerable. In both target organs, tumor formation was preceded by hyperplasia, which could represent the main mechanism of carcinogenic action. The dose-response relationship for this effect was investigated in male F344 rats after 4-week feeding with CA at different dietary concentrations (0, 0.05, 0.14, 0.40, and 1.64%). Cells in S-phase of DNA replication were visualized by immunohistochemical analysis of incorporated 5-bromo-2'-deoxyuridine (BrdU), 2 hr after intraperitoneal injection. In the forestomach, both the total number of epithelial cells per millimeter section length and the unit length labeling index of BrdU-positive cells (ULLI) were increased, about 2.5-fold, at 0.40 and 1.64%. The lowest concentration (0.05%) had no effect. At 0.14%, both variables were decreased by about one-third. In the kidney, the labeling index in proximal tubular cells also indicated a J-shaped (or U-shaped) dose response with a 1.8-fold increase at 1.64%. In the glandular stomach and in the liver, which are not target organs, no dose-related effect was seen. The data show a good correlation between the organ specificity for cancer induction and stimulation of cell division. With respect to the dose-response relationship and the corresponding extrapolation of the animal tumor data to a human cancer risk, a linear extrapolation appears not to be appropriate.

Lutz U et al; Fundamental Applied Toxicology 39(2): 131-137 (1997)


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