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Technical details about Tox21_300980, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 84-74-2, Di-n-butyl phthalate, N-butyl phthalate, Butyl phthalate, Genoplast b, Palatinol c
Molecular Formula
C16H22O4
Molecular Weight
278.34  g/mol
InChI Key
DOIRQSBPFJWKBE-UHFFFAOYSA-N
FDA UNII
2286E5R2KE

A plasticizer used in most plastics and found in water, air, soil, plants and animals. It may have some adverse effects with long-term exposure.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
dibutyl benzene-1,2-dicarboxylate
2.1.2 InChI
InChI=1S/C16H22O4/c1-3-5-11-19-15(17)13-9-7-8-10-14(13)16(18)20-12-6-4-2/h7-10H,3-6,11-12H2,1-2H3
2.1.3 InChI Key
DOIRQSBPFJWKBE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC
2.2 Other Identifiers
2.2.1 UNII
2286E5R2KE
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Butyl Phthalate

2. Di N Butyl Phthalate

3. Di-n-butyl Phthalate

4. Phthalate, Butyl

5. Phthalate, Di-n-butyl

6. Phthalate, Dibutyl

2.3.2 Depositor-Supplied Synonyms

1. 84-74-2

2. Di-n-butyl Phthalate

3. N-butyl Phthalate

4. Butyl Phthalate

5. Genoplast B

6. Palatinol C

7. Celluflex Dpb

8. Polycizer Dbp

9. Unimoll Db

10. Staflex Dbp

11. Elaol

12. Ergoplast Fdb

13. Witcizer 300

14. Kodaflex Dbp

15. Hexaplas M/b

16. Dibutylphthalate

17. Dibutyl 1,2-benzenedicarboxylate

18. Dibutyl-o-phthalate

19. Dibutyl Benzene-1,2-dicarboxylate

20. Phthalic Acid Dibutyl Ester

21. 1,2-benzenedicarboxylic Acid, Dibutyl Ester

22. Dbp (ester)

23. N-butylphthalate

24. Dibutyl-phthalate

25. Ersoplast Fda

26. Phthalate, Di-n-butyl

27. Uniflex Dbp

28. Hatcol Dbp

29. Dibutyl O-phthalate

30. Rc Plasticizer Dbp

31. Benzene-o-dicarboxylic Acid Di-n-butyl Ester

32. Phthalic Acid, Dibutyl Ester

33. O-benzenedicarboxylic Acid, Dibutyl Ester

34. Rcra Waste Number U069

35. Px 104

36. Ortho-dibutyl Phthalate

37. Phthalic Acid Di-n-butyl Ester

38. Di-n-butylorthophthalate

39. Monocizer Dbp

40. Plasthall Dbp

41. Dibutyl-1,2-benzenedicarboxylate

42. Dibutylphthatlate

43. Vestinol C

44. Hatco Dbp

45. Palatinol Dbp

46. Dibutyl Phthalated

47. Nsc 6370

48. Di-n-butyl Phthalate (dbup)

49. Corflex 440

50. Morflex 240

51. Ruifeng Vp 201

52. Uniplex 150

53. Di-n-butylester Kyseliny Ftalove

54. Chebi:34687

55. Yh-1bd2

56. Nsc-6370

57. 1,2-benzenedicarboxylic Acid, 1,2-dibutyl Ester

58. O-benzenedicarboxylic Acid Dibutyl Ester

59. 1,2-benzenedicarboxylic Acid Dibutyl Ester

60. Chembl272485

61. Dtxsid2021781

62. Benzene-o-dicarboxylic Acid, Di-n-butyl Ester

63. Vp-201

64. 2286e5r2ke

65. Benzenedicarboxylic Acid Dibutyl Ester

66. 1,2-dibutyl Benzene-1,2-dicarboxylate

67. Dsstox_cid_1781

68. Dibutyl Ester Of 1,2-benzenedicarboxylic Acid

69. Dsstox_rid_76324

70. Dsstox_gsid_21781

71. Phthalate, Dibutyl-

72. Caswell No. 292

73. Nutyl Phthalate

74. Dibutyl Phthalate (dbp)

75. Phthalate, Butyl

76. Cas-84-74-2

77. Phthalate, Dibutyl

78. Ccris 2676

79. Hsdb 922

80. Di N Butyl Phthalate

81. Rapidcelltrade Markp

82. Dibutyl Phthalate [nf]

83. Sr-05000001549

84. Einecs 201-557-4

85. Rcra Waste No. U069

86. Epa Pesticide Chemical Code 028001

87. Brn 1914064

88. Di-n-butylester Kyseliny Ftalove [czech]

89. Bufa

90. Unii-2286e5r2ke

91. Ai-3-00283

92. Dibutyll Phthalate

93. Mfcd00009441

94. Benzenedicarboxylic Acid, Dibutyl Ester

95. Spectrum_001975

96. Di(1-butyl) Phthalate

97. Specplus_000628

98. Dibutyl Phthalate, 99%

99. Spectrum3_000874

100. Spectrum4_000714

101. Spectrum5_002068

102. Epitope Id:138714

103. Ec 201-557-4

104. Wln: 4ovr Bvo2

105. Dibutyl Phthalate, >=99%

106. Schembl24051

107. Bspbio_002547

108. Kbiogr_001267

109. Kbioss_002541

110. Spectrum330086

111. Mls002177802

112. Bidd:er0641

113. Divk1c_006724

114. Dibutyl Phthalate [ii]

115. Dibutyl Phthalate [mi]

116. Phthalic Acid, Bis-butyl Ester

117. Gtpl6295

118. Dibutyl Phthalate [hsdb]

119. Dibutyl Phthalate [inci]

120. Kbio1_001668

121. Kbio2_002532

122. Kbio2_005100

123. Kbio2_007668

124. Kbio3_002047

125. Butyl Phthalate [who-dd]

126. Nsc6370

127. Dibutyl Phthalate [mart.]

128. Dibutyl Phthalate, Ar, >=99%

129. Dibutyl Phthalate, Lr, >=98%

130. Dibutyl 1, 2-benzenedicarboxylate

131. Hms2091e09

132. Hms3041e18

133. Pharmakon1600-00330086

134. Dibutyl Phthalate [usp-rs]

135. Bcp24796

136. Hy-y0304

137. Zinc1693431

138. Dibutyl Phthalate, Selectophore(tm)

139. Tox21_201729

140. Tox21_300980

141. Bbl011532

142. Bdbm50371946

143. Nsc755894

144. Stl146650

145. Akos005720807

146. Ccg-230933

147. Db13716

148. Nsc-755894

149. Dibutyl Phthalate [ep Monograph]

150. Ncgc00090769-01

151. Ncgc00090769-02

152. Ncgc00090769-03

153. Ncgc00090769-04

154. Ncgc00090769-05

155. Ncgc00090769-06

156. Ncgc00090769-07

157. Ncgc00090769-08

158. Ncgc00090769-09

159. Ncgc00254882-01

160. Ncgc00259278-01

161. Smr000777923

162. Sbi-0052568.p002

163. Cs-0013564

164. Dibutyl Phthalate, Reagentplus(r), >=99%

165. Ft-0624680

166. P0292

167. S5377

168. Dibutyl Phthalate, Saj Special Grade, >=98.0%

169. Q415612

170. J-503795

171. Sr-05000001549-1

172. Sr-05000001549-3

173. Araldite(r) Resins(modified Epoxy Resins),grade 502

174. Brd-k73477617-001-01-0

175. Brd-k73477617-001-04-4

176. Dibutyl Phthalate, Pestanal(r), Analytical Standard

177. F0001-2134

178. Z277540112

179. Dibutyl Phthalate, Certified Reference Material, Tracecert(r)

180. Phthalic Acid, Bis-butyl Ester 100 Microg/ml In Acetonitrile

181. Phthalic Acid, Bis-butyl Ester 100 Microg/ml In Cychohexane

182. Dibutyl Phthalate, European Pharmacopoeia (ep) Reference Standard

183. Dibutyl Phthalate, United States Pharmacopeia (usp) Reference Standard

184. Dibutyl Phthalate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 278.34 g/mol
Molecular Formula C16H22O4
XLogP34.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count10
Exact Mass278.15180918 g/mol
Monoisotopic Mass278.15180918 g/mol
Topological Polar Surface Area52.6 Ų
Heavy Atom Count20
Formal Charge0
Complexity271
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Scrub typhus, a rickettsial disease transmitted by larvae of Leptotrombidium deliense, is of special importance to the Armed Forces personnel, due to the heightened risk to this disease during movement in mite endemic areas during exercise/war. The disease is best prevented by the use of personal protective measures including repellents. Studies were undertaken to determine the relative efficacy of repellents: diethyl toulamide (DEET), dibutyl phthalate (DBP) with an indigenously developed repellent diethyl phenyl acetamide (DEPA) against the larval trombiculid mite. The repellents were tested for persistence on impregnated cloth prior to washing, post washing and ironing by means of a specially fabricated testing kit. Acaricidal efficacy estimation was performed on the treated fabrics and topical application efficacy of repellents on mice was evaluated by a novel animal testing model. DEET and DEPA were found to provide maximum protection (repellence and acaricidal efficacy), could withstand two launderings of the impregnated uniform and also had superior efficacy on topical application (8 h). Ironing was found to significantly reduce the repellence of DEET and DBP. The findings of this study point towards the superiority of DEPA and DEET for impregnation of the uniform cloth as well as for topical application for the prevention of scrub typhus amongst the troops.

PMID:11525158 Tilak R et al; Indian J Med Res 113: 98-102 (2001)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Plasticizers

Materials incorporated mechanically in plastics (usually PVC) to increase flexibility, workability or distensibility; due to the non-chemical inclusion, plasticizers leach out from the plastic and are found in body fluids and the general environment. (See all compounds classified as Plasticizers.)


5.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03B - Insecticides and repellents

P03BX - Other insecticides and repellents

P03BX03 - Dibutylphthalate


5.3 Absorption, Distribution and Excretion

Dibutyl phthalate administered orally to rats and mice /was/ rapidly absorbed and excreted in urine and feces within 48 hr. Max concentrations in blood /SRP: not DBP itself but a metabolite/ plasma & various organs /occurred/ at 20-30 min; /concentrations were/ greater in liver than fat and spleen.

IOKU ET AL; OSAKA FURITSU KOSHU EISEI KENKYUSHO KENKYU HOKOKU, YAKUJI SHIDO HEN 10: 57 (1976)


Dibutyl phthalate given orally to rats was excreted in urine 30.6-43.5% and in feces 20.0-22.0% in 24 hr. Amounts absorbed by fetuses were approximately /the/ same as by fat tissues.

IOKU ET AL; OSAKA FURITSU KOSHU EISEI KENKYUSHO KENKYU HOKOKU, YAKUJI SHIDO HEN 10: 57 (1976)


Dibutyl phthalate was detected in the bile of rats after oral administration. ... A small part of the dose was absorbed intact through the intestine.

USEPA/ECAO; Phthalate Atlas Report p.IV-2 (1980)


The presence of phthalate esters in the blood of individuals /who had/ ingested food /that/ had been in contact with flexible plastics ... dibutyl phthalate levels detected in the blood were much higher than prior to eating the food in the plastic packaging system ... dibutyl phthalate levels in blood /were/ 0.35 ppm ... compared to an average value of 0.02 ppm prior to the meals.

USEPA/ECAO; Phthalate Atlas Report p.IV-2 (1980)


For more Absorption, Distribution and Excretion (Complete) data for DIBUTYL PHTHALATE (25 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

An individual (male, 36 years, 87 kg) ingested two separate doses of di-n-butyl phthalate (DnBP) and diisobutyl phthalate (DiBP) at a rate of approximately 60 ug/kg. Key monoester and oxidized metabolites were identified and quantified in urine continuously collected until 48 hr post-dose. For both DnBP and DiBP, the majority of the dose was excreted in the first 24 hr (92.2 % of DnBP, 90.3 % of DiBP), while only <1 % of the dose was excreted in urine on day 2. In each case, the simple monoesters were the major metabolites (MnBP, 84 %; MiBP, 71 %). For DnBP, approximately 8 % was excreted as various side chain oxidized metabolites. For DiBP, approximately 20 % was excreted mainly as the oxidized side chain metabolite 2OH-MiBP, indicating that the extent of oxidative modification is around 2.5 times higher for DiBP than for DnBP. All DnBP and DiBP metabolites reached peak concentrations between 2 and 4 hr post-exposure, followed by a monotonic decline. For DnBP metabolites, the elimination halftime of MnBP was 2.6 hr; longer elimination halftimes were estimated for the oxidized metabolites (2.9-6.9 hr). For DiBP metabolites, MiBP had the shortest halftime (3.9 hr), and the oxidized metabolites had somewhat longer halftimes (4.1 and 4.2 hr). Together with the simple monoesters, secondary oxidized metabolites are additional and valuable biomarkers of phthalate exposure. This study provides basic human metabolism and toxicokinetic data for two phthalates that have to be considered human reproductive toxicants and that have been shown to be omnipresent in humans.

PMID:22820759 Koch HM et al; Arch Toxicol. 86 (12): 1829-39 (2012)


Main urinary metabolite of (14)C-dibutyl phthalate in the rat, guinea pig and hamster ... the monoester, MBP and its glucuronide. ... small amount of phthalic acid, unchanged DBP and omega and omega-1 oxidation products of MBP.

USEPA/ECAO; Phthalate Atlas Report p.IV-8 (1980)


Metabolites found in rat urine after a single oral dose of (14)C-dibutyl phthalate included: phthalic acid, mono-butyl phthalate, mono-(3-hydroxy-butyl) phthalate, and mono-(4-hydroxy butyl) phthalate.

USEPA/ECAO; Phthalate Atlas Report p.II-11 (1980)


The primary route of MBuP, the major DBP metabolite, elimination in rodents and humans is urinary excretion. The monobutylphthalate glucuronide appears to be the primary metabolite identified in rat urine ... . MBuP is excreted into the bile (about 45%), but only about 5% is eliminated in the feces, indicating that efficient enterohepatic recirculation occurs ... . Biliary metabolites of DBP include monobutylphthalate, monobutylphthalate glucuronide, and oxidized monobutylphthalate glucuronide metabolites ... . Mice are known to excrete higher amounts of glucuronidated phthalate ester metabolites than rats and primates excrete higher levels of glucuronidated phthalate ester metabolites than mice. ...

NTP/CERHR; Monograph on the Potential Human Reproductive and Developmental Effects of Di-n-Butyl Phthalate (DBP) p. II-10. Available from, as of April 17, 2008: https://cerhr.niehs.nih.gov/evals/index.html


For more Metabolism/Metabolites (Complete) data for DIBUTYL PHTHALATE (21 total), please visit the HSDB record page.


5.5 Biological Half-Life

Whole body (animal studies): virtually all eliminated within 48 hours; [TDR, p. 473]

TDR - Ryan RP, Terry CE, Leffingwell SS (eds). Toxicology Desk Reference: The Toxic Exposure and Medical Monitoring Index, 5th Ed. Washington DC: Taylor & Francis, 1999., p. 473


5.6 Mechanism of Action

One proposed mechanism of /testicular/ toxicity involves a disturbance in the interaction between germ cells and Sertoli cells. The Sertoli cell-germ cell interaction is generally considered to be required for the differentiation of male germ cells and their progression through the seminiferous epithelium and release as mature spermatozoa. Exposure to di-n-butyl phthalate is associated with both the release of iron from hemoglobin and/or transferrin in the liver and spleen, and the subsequent depletion of iron in the blood and testes. The decreased amount of available iron results in a decrease in succinate dehydrogenase activity in the Sertoli cells, resulting in disturbances in the energy transfer system between Sertoli cells and germ cells; anoxia due to iron depletion and/or disturbances in the energy supply may induce the sloughing of germ cells. Decreases in testicular sorbitol, fructose, and glucose levels have been observed in the testes 3-12 hours post exposure. Two days after exposure, there were significant decreases in sorbitol dehydrogenase and succinate dehydrogenase activities and decreases in testicular iron and zinc levels.

U.S. Dept Health & Human Services/Agency for Toxic Substances & Disease Registry; Toxicological Profile for DI-n-BUTYL PHTHALATE p.83 (September 2001) No. 135. Available from, as of April 22, 2008: https://www.atsdr.cdc.gov/toxpro2.html#


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