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Chemistry

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Also known as: 1934-21-0, Acid yellow 23, Yellow 5, Food yellow 4, Aizen tartrazine, Fd & c yellow no. 5
Molecular Formula
C16H9N4Na3O9S2
Molecular Weight
534.4  g/mol
InChI Key
UJMBCXLDXJUMFB-UHFFFAOYSA-K

Tartrazine
An anionic, hydrophilic azo dye with an orange-yellow color used in fabrics, foods and cosmetics, and as a biological stain.
1 2D Structure

Tartrazine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4H-pyrazole-3-carboxylate
2.1.2 InChI
InChI=1S/C16H12N4O9S2.3Na/c21-15-13(18-17-9-1-5-11(6-2-9)30(24,25)26)14(16(22)23)19-20(15)10-3-7-12(8-4-10)31(27,28)29;;;/h1-8,13H,(H,22,23)(H,24,25,26)(H,27,28,29);;;/q;3*+1/p-3
2.1.3 InChI Key
UJMBCXLDXJUMFB-UHFFFAOYSA-K
2.1.4 Canonical SMILES
C1=CC(=CC=C1N=NC2C(=NN(C2=O)C3=CC=C(C=C3)S(=O)(=O)[O-])C(=O)[O-])S(=O)(=O)[O-].[Na+].[Na+].[Na+]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Barium, Tartrazine

2. Fd And C Yellow No. 5

3. Tartrazine Barium

4. Tartrazine Barium (2:3)

2.2.2 Depositor-Supplied Synonyms

1. 1934-21-0

2. Acid Yellow 23

3. Yellow 5

4. Food Yellow 4

5. Aizen Tartrazine

6. Fd & C Yellow No. 5

7. Fd&c Yellow No. 5

8. 1342-47-8

9. Trisodium Salt

10. C.i. Acid Yellow 23

11. A.f. Yellow No. 4

12. Tartrazine Fd&c Yellow #5

13. Tartraphenine

14. Atul Tartrazine

15. Erio Tartrazine

16. Kako Tartrazine

17. Tartran Yellow

18. Tartrazine Lake

19. Tartrazine B

20. Tartrazine C

21. Tartrazine G

22. Tartrazine M

23. Tartrazine N

24. Tartrazine O

25. Tartrazine T

26. Ci 19140

27. Hd Tartrazine

28. Hydrazine Yellow

29. Lake Yellow

30. Sugai Tartrazine

31. Tartrazine Fq

32. Tartrazine Ns

33. Tartrazine Xx

34. Tartrazol Yellow

35. Wool Yellow

36. Tartrazine Xxx

37. Tartrazine Mcgl

38. Tartrazol Bpc

39. Amacid Yellow T

40. Cilefa Yellow T

41. Dye Yellow Lake

42. Fenazo Yellow T

43. Kayaku Tartrazine

44. Mitsui Tartrazine

45. Oxanal Yellow T

46. Tartar Yellow N

47. Tartar Yellow S

48. Tartrazine Yellow

49. Kiton Yellow T

50. Lemon Yellow A

51. Acid Yellow T

52. Bucacid Tartrazine

53. Dolkwal Tartrazine

54. Hexacol Tartrazine

55. Hidazid Tartrazine

56. Acilan Yellow Gg

57. C.i. 19140

58. Egg Yellow A

59. San-ei Tartrazine

60. Tartar Yellow Fs

61. Tartar Yellow Pf

62. Airedale Yellow T

63. Canacert Tartrazine

64. Food Yellow 5

65. Neklacid Yellow T

66. Tartrine Yellow O

67. Eurocert Tartrazine

68. Vondacid Tartrazine

69. Hydroxine Yellow L

70. Tartrazine C Extra

71. Calcocid Yellow Xx

72. Kca Tartrazine Pf

73. Yellow Lake 69

74. Naphtocard Yellow O

75. Tartrazine A Export

76. Hd Tartrazine Supra

77. Calcocid Yellow Mcg

78. Tartrazine Yellow 5

79. Yellow No. 5

80. Tartrazine A Expo T

81. Tartrazine B.p.c.

82. 12225-21-7

83. D&c Yellow 5

84. Food Yellow No. 4

85. Lemon Yellow A Geigy

86. Schultz No. 737

87. Maple Tartrazol Yellow

88. Acid Leather Yellow T

89. C.i. 640

90. Unitertracid Yellow Te

91. Yellow No. 5 Fdc

92. Curon Fast Yellow 5g

93. Fd And C Yellow 5

94. 1310 Yellow

95. 1409 Yellow

96. Xylene Fast Yellow Gt

97. Hispacid Fast Yellow T

98. Usacert Yellow No. 5

99. C.i. Food Yellow 4

100. Hexacert Yellow No. 5

101. Chebi:9405

102. Fd&g Yellow No. 5

103. Tartrazine Extra Pure A

104. L Yellow Z 1020

105. Tartrazine Lake Yellow N

106. Edicol Supra Tartrazine N

107. D And C Yellow No. 5

108. Kca Foodcol Tartrazine Pf

109. Certicol Tartrazol Yellow S

110. Tartrazine O Specially Pure

111. Tartrazine Xx Specially Pure

112. Trisodium 5-oxo-1-(4-sulfonatophenyl)-4-(4-sulfonatophenyl)diazenyl-4h-pyrazole-3-carboxylate

113. Dye Fd And C Yellow No. 5

114. Tartrazine Fd & C Yellow #5

115. E102

116. Kayaku Food Colour Yellow No. 4

117. C.i. Acid Yellow 23, Trisodium Salt

118. Trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate

119. M-8847

120. Nsc4760

121. Zlut Kysela 23

122. 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-4-((4-sulfophenyl)azo)-1h-pyrazole-3-carboxylic Acid, Trisodium Salt

123. Trisodium 5-oxo-1-(4-sulfonatophenyl)-4-[(e)-(4-sulfonatophenyl)diazenyl]-4,5-dihydro-1h-pyrazole-3-carboxylate

124. Zlut Pigment 100

125. Zlut Potravinarska 4

126. 3-carboxy-5-hydroxy-1-p-sulfophenyl-4-p-sulfophenylazopyrazole Trisodium Salt

127. L-gelb 2

128. L-gelb 2 [german]

129. Zlut Kysela 23 [czech]

130. Unii-i753wb2f1m

131. Zlut Pigment 100 [czech]

132. Zlut Potravinarska 4 [czech]

133. Tri Sodium Salt

134. Ccris 2656

135. Hsdb 7216

136. Fd & C Yellow No. 5 Tartrazine

137. Nsc 4760

138. Trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(e)-(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate

139. Food Yellow No.4

140. Einecs 217-699-5

141. E 102

142. Epitope Id:124945

143. Tartrazine, Analytical Standard

144. Acid Yellow 23 Aluminium Lake

145. Tartrazine, P.a., 95-105%

146. Tartrazine, Dye Content >=85 %

147. Amy22425

148. Trisodium Salt Of 3-carboxy-5-hydroxy-1-sulfophenylazopyrazole

149. Tartrazine 100 Microg/ml In Water

150. Tartrazine, For Microscopy (hist.)

151. 1-(4-sulfophenyl)-4-((4-sulfophenyl)azo)-1h-pyrazole-3-carboxylic

152. Mfcd00148908

153. Akos015903034

154. Akos016010270

155. Trisodium 3-carboxy-5-hydroxy-1-p-sulfophenyl-4-p-sulfophenylazopyrazole

156. Trisodium 5-hydroxy-1-(4-sulphophenyl)-4-(4-sulphophenylazo)pyrazole-3-carboxylate

157. Bp-31013

158. Trisodium 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-4-((4-sulfophenyl)azo)-1h-pyrazole-3-carboxylate

159. Trisodium 5-oxo-1-(4-sulfonatophenyl)-4-[(e)-(4-sulfonatophenyl)d Iazenyl]-4,5-dihydro-1h-pyrazole-3-carboxylate

160. Y-4

161. Ft-0621860

162. C.i. Acid Yellow 23, Trisodium Salt (van)

163. C07574

164. D90635

165. Q407158

166. W-107716

167. Tartrazine Lake, Ci No 19140:1 , Fd & C Yellow 5 Lake

168. 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-4-((4-sulfophenyl)azo)-1h-pyrazole-3-carboxylic Acid

169. 5-oxo-1-(4-sulfophenyl)-4-[(e)-(4-sulfophenyl)azo]-4h-pyrazole-3-carboxylic Acid

170. 1h-pyrazole-3-carboxylic Acid, 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-4-(2-(4-sulfophenyl)diazenyl)-, Sodium Salt (1:3)

171. 4,5-dihydro-5-oxo-1-(4-sulfophenyl)-4-(4-sulfophenyl)azo-1h-pyrazole-3-carboxylic Acid Trisodium Salt

172. Pyrazole-3-carboxylic Acid, 5-hydroxy-1-(p-sulfophenyl)-4-(p-sulfophenyl)azo-, Trisodium Salt

173. Sodium (e)-5-oxo-1-(4-sulfonatophenyl)-4-((4-sulfonatophenyl)diazenyl)-4,5-dihydro-1h-pyrazole-3-carboxylate

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 534.4 g/mol
Molecular Formula C16H9N4Na3O9S2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count12
Rotatable Bond Count3
Exact Mass533.95040307 g/mol
Monoisotopic Mass533.95040307 g/mol
Topological Polar Surface Area229 Ų
Heavy Atom Count34
Formal Charge0
Complexity949
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count4
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Food Coloring Agents

Natural or synthetic dyes used as coloring agents in processed foods. (See all compounds classified as Food Coloring Agents.)


Coloring Agents

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)


4.2 Absorption, Distribution and Excretion

... The fate of the pyrazole fragment of Tartrazine /was examined/ using sulphur-35 labelled Tartrazine and 1-(4-sulphophenyl)-3-methyl-4-(4-sulphophenylazo)-5-pyrazolone (SPMP an analogue of Tartrazine) and carbon-14 labeled SPMP. Following oral administration, both Tartrazine and SPMP labeled with sulphur-35 were predominantly excreted in feces (90 and 89 % of the dose respectively after 72 hours) with small amounts in urine (8 and 7.2 % of the dose, respectively, after 72 hours). The urinary radioactivity excreted in 48 hours with sulphanilic acid and 4-sulphophenylhydrazine was 23 and 23 % after Tartrazine administration, and 54 and 22 % after SPMP administration; the remaining radioactivity was not characterized.

European Food Safety Authority (EFSA); Scientific Opinion of the ANS Panel on the re-evaluation Tartrazine (E 102) Published: 12 November 2009 Available from, as of June 28, 2011: https://www.efsa.europa.eu/en/publications.htm


... The metabolism of carbon-14 Tartrazine randomly labeled in the phenyl azo group /was studied/ in rat, rabbit and human. In both animal species Tartrazine was administered orally and intraperitoneally whilst humans received oral Tartrazine. ... After intraperitoneal administration to 6 rats of 2.4 mg/kg bw of Tartrazine, between 64 and 96 % of the dose was recovered unchanged in urine within 24 hours; no other products were reported. In rabbit, at a dose of 2.4 mg/kg bw of Tartrazine administered intraperitoneally, 94 % of the dose was recovered unchanged in urine within 24 hours, with a further 1.4 % recovered as conjugated sulphanilic acid. However, after an intraperitoneal dose of 1000 mg in the rabbit ... only 57.3% was recovered unchanged in urine within 24 hours, with a further 25.7 and 6 % recovered as free and conjugated sulphanilic acid, respectively. After oral administration to 3 rats at 5 mg/rat ..., no free Tartrazine was measured but means of 28 and 34.6 % were recovered in urine as free and conjugated sulphanilic acid, respectively. In the rabbit dosed 1000 mg ... 8.2 % was recovered unchanged in urine within 24 hours with a further 27 and 26.8 % as free and conjugated sulphanilic acid respectively within 72 hours. In 4 humans receiving a single capsule containing 89-100 mg of Tartrazine ..., no free Tartrazine was measured in urine for any subject; in one subject 106 % was recovered as free sulphanilic acid whilst for the other 3 subjects mean recoveries of free and conjugated sulphanilic acid were 40.6 and 49.7 % respectively. ...

European Food Safety Authority (EFSA); Scientific Opinion of the ANS Panel on the re-evaluation Tartrazine (E 102) Published: 12 November 2009 Available from, as of June 28, 2011: https://www.efsa.europa.eu/en/publications.htm


Low biliary excretion of Tartrazine (1 %) /was demonstrated/ following intravenous administration of an unspecified dose. ... low biliary excretion was due to the carboxyl group. After a dose of 2 mg ... unchanged Tartrazine could be detected in bile, but there was no evidence of ring fission products. Following intraperitoneal injection, an unidentified and unquantified Tartrazine conjugate was rapidly excreted in bile, but again none of the previously reported reductive ring fission products.

European Food Safety Authority (EFSA); Scientific Opinion of the ANS Panel on the re-evaluation Tartrazine (E 102) Published: 12 November 2009 Available from, as of June 28, 2011: https://www.efsa.europa.eu/en/publications.htm


4.3 Metabolism/Metabolites

After oral administration there is extensive metabolism of Tartrazine by the gastrointestinal microflora to sulphanilic acid and aminopyrazalone (which may then be subsequently cleaved to sulphanilic acid and alpha-amino-beta-ketobutyric acid fragments with the latter breaking down further via intermediary metabolism with release of carbon dioxide).

European Food Safety Authority (EFSA); Scientific Opinion of the ANS Panel on the re-evaluation Tartrazine (E 102) Published: 12 November 2009 Available from, as of June 28, 2011: https://www.efsa.europa.eu/en/publications.htm


Absorption and metabolism of (14)C-labelled tartrazine (FD & C Yellow No. 5) and high molecular weight polymeric derivatives were compared in rats. A trace to 1.5% of unchanged monomeric dyes was excreted in urine and bile during the first 24 hr after dosing. No unchanged dye was absorbed after administration of the polymeric derivatives. ...In animals dosed with tartrazine and its polymer derivative, absorption of the cleavage product aminopyrazolone and its metabolites was 4.0 and 4.6%, respectively. Azo bond cleavage did not appear to be decreased in the polymer derivatives. However, the sulphanilic acid moiety of both dyes remained attached to the polymer backbone, resulting in a 95% decrease in sulphanilic acid absorption with polymeric tartrazine.

PMID:602250 Honohan T et al; Xenobiotica 7 (12): 765-774 (1977)


The 4-sulphophenylhydrazine metabolite was also labeled with sulphur-35 and administered orally and intraperitoneally. Excretion of this metabolite differed with the route of administration (35 and 49 % in urine and feces, respectively, 48 hours following oral, and 90 and 5 % in urine and feces, respectively, 48 hours following intraperitoneal administration). Following oral administration, 69 % of urinary radioactivity excreted in 48 hours was sulphanilic acid and 21 % was 4-sulphophenylhydrazine, whereas following intraperitoneal administration, 9 % of urinary radioactivity excreted in 48 hours was sulphanilic acid and 73% was 4-sulphophenylhydrazine. These data suggest there is a marked conversion of 4- sulphophenylhydrazine to sulphanilic acid presumably in the gut lumen. /4-sulphophenylhydrazine/

European Food Safety Authority (EFSA); Scientific Opinion of the ANS Panel on the re-evaluation Tartrazine (E 102) Published: 12 November 2009 Available from, as of June 28, 2011: https://www.efsa.europa.eu/en/publications.htm


4.4 Mechanism of Action

... Blocking studies showed that tartrazine contraction was inhibited by atropine alone but not by any other blocking agent tested, implying that tartrazine acts either directly or indirectly upon the muscarinic acetylcholine receptor associated with parasympathetic innervation.

PMID:1570631 Hutchinson AP et al; Toxicol Lett 60 (2): 165-73 (1992)


The ability of selected food colors to interact with isolated guinea-pig ileum was investigated using a gut bath system. Studies revealed that guinea-pig ileum was specifically sensitive to tartrazine. Intestinal contraction occurred dose-dependently down to a minimum effective dose of 10 uM. ...Studies investigating the biological activity of structural analogues of tartrazine revealed the ability to initiate intestinal contraction was associated with the presence of the carboxylic acid residue at the R1 position of the pyrazole ring. Blocking studies showed that tartrazine contraction was inhibited by atropine alone but not by any other blocking agent tested, implying that tartrazine acts either directly or indirectly upon the muscarinic acetylcholine receptor associated with parasympathetic innervation.

PMID:1570631 Hutchinson AP et al; Toxicol Lett 60 (2): 165-73 (1992)


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