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2D Structure
Also known as: Butyl 4-hydroxybenzoate, 94-26-8, Butyl paraben, Butyl p-hydroxybenzoate, Butyl parahydroxybenzoate, Nipabutyl
Molecular Formula
C11H14O3
Molecular Weight
194.23  g/mol
InChI Key
QFOHBWFCKVYLES-UHFFFAOYSA-N
FDA UNII
3QPI1U3FV8

butylparaben is a natural product found in Strychnos cathayensis with data available.
Butylparaben is a Standardized Chemical Allergen. The physiologic effect of butylparaben is by means of Increased Histamine Release, and Cell-mediated Immunity.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butyl 4-hydroxybenzoate
2.1.2 InChI
InChI=1S/C11H14O3/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7,12H,2-3,8H2,1H3
2.1.3 InChI Key
QFOHBWFCKVYLES-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCCCOC(=O)C1=CC=C(C=C1)O
2.2 Other Identifiers
2.2.1 UNII
3QPI1U3FV8
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Butyl-p-hydroxybenzoate

2.3.2 Depositor-Supplied Synonyms

1. Butyl 4-hydroxybenzoate

2. 94-26-8

3. Butyl Paraben

4. Butyl P-hydroxybenzoate

5. Butyl Parahydroxybenzoate

6. Nipabutyl

7. Butoben

8. Butyl Chemosept

9. Butyl Parasept

10. Tegosept B

11. Butyl Tegosept

12. Butyl Butex

13. Tegosept Butyl

14. Aseptoform Butyl

15. Preserval B

16. Solbrol B

17. N-butyl P-hydroxybenzoate

18. Butyl-parasept

19. Benzoic Acid, 4-hydroxy-, Butyl Ester

20. 4-(butoxycarbonyl)phenol

21. N-butyl 4-hydroxybenzoate

22. N-butyl Parahydroxybenzoate

23. N-butyl Hydroxybenzoate

24. Butyl P-hydroxy Benzoate

25. Fema No. 2203

26. N-butyl-p-hydroxybenzoate

27. 4-hydroxybenzoic Acid Butyl Ester

28. Benzoic Acid, P-hydroxy-, Butyl Ester

29. N-butyl-paraben

30. P-hydroxybenzoic Acid Butyl Ester

31. Lexgard B

32. N-butyl-4-hydroxybenzoate

33. Nsc 8475

34. P-hydroxybenzoic Acid N-butyl Ester

35. Butylparaben (nf)

36. Butylparaben (tn)

37. Butylparaben [nf]

38. Spf

39. P-hydroxybenzoic Acid, Butyl Ester

40. 4-hydroxybenzoic Acid, Butyl Ester

41. P-hydroxybenzoic Butyl Ester

42. 3qpi1u3fv8

43. Butyl Parahydroxybenzoate (tn)

44. Chebi:88542

45. 4-hydroxybenzoic Acid-n-butyl Ester

46. Nsc-13164

47. Cas-94-26-8

48. Ncgc00016354-03

49. Dsstox_cid_209

50. Dsstox_rid_75434

51. Dsstox_gsid_20209

52. Butylparaben [usan]

53. Butyl-p-hydroxybenzoate

54. Caswell No. 130a

55. Fema Number 2203

56. N-butyl Paraben

57. 4-hydroxybenzoic Acid-n-butyl Ester 1000 Microg/ml In Acetonitrile

58. Butyl Par Asept

59. Smr000462402

60. Ccris 2462

61. Hsdb 286

62. P-hydroxy Butyl Benzoate

63. Sr-01000389296

64. Einecs 202-318-7

65. Unii-3qpi1u3fv8

66. Epa Pesticide Chemical Code 061205

67. Brn 1103741

68. Butyl-paraben

69. Ai3-02930

70. 27k

71. Mfcd00016478

72. Butyl Paraben-[d9]

73. 4mg9

74. Prestwick0_000894

75. Prestwick1_000894

76. Prestwick2_000894

77. Prestwick3_000894

78. Butylparaben [ii]

79. Butylparaben [mi]

80. Wln: Qr Dvo4

81. Butylparaben [hsdb]

82. Butylparaben [inci]

83. Cid_7184

84. Schembl3647

85. Butylparaben [vandf]

86. Bspbio_000708

87. Butyl //p//-hydroxybenzoate

88. Mls000575004

89. Mls002154054

90. Mls002303045

91. Bidd:er0231

92. Butylparaben [usp-rs]

93. Spbio_002917

94. Bpbio1_000780

95. Chembl459008

96. F0266-0124

97. N-butyl-p-hydroxybenzoate,(s)

98. Dtxsid3020209

99. Bdbm23448

100. Fema 2203

101. Nsc8475

102. Butyl Parahydroxybenzoate (jp15)

103. Butyl Parahydroxybenzoate (jp17)

104. Butyl 4-hydroxybenzoate, >=99%

105. Butyl Para Hydroxy Benzoate

106. Hms1570d10

107. Hms2094a21

108. Hms2097d10

109. Hms2220g15

110. Hms3327p04

111. Hms3714d10

112. Pharmakon1600-01505995

113. Hy-b1431

114. Nsc-8475

115. Zinc1586769

116. Tox21_110393

117. Tox21_201785

118. Tox21_300332

119. Nsc759303

120. P-hydroxybenzoic Acid, N-butyl Ester

121. S4584

122. Butyl Hydroxybenzoate [mart.]

123. Akos000121421

124. Butyl Hydroxybenzoate [who-dd]

125. Tox21_110393_1

126. Butyl Parahydroxybenzoate [jan]

127. Ccg-213596

128. Cs-4783

129. Db14084

130. Nsc-759303

131. Butyl P-hydroxy Benzoate [fhfi]

132. Butyl 4-?hydroxybenzoate(butyl Paraben)

133. Butyl 4-hydroxybenzoate (butyl Paraben)

134. Ncgc00016354-01

135. Ncgc00016354-02

136. Ncgc00016354-04

137. Ncgc00016354-05

138. Ncgc00016354-06

139. Ncgc00016354-07

140. Ncgc00016354-11

141. Ncgc00091142-01

142. Ncgc00091142-02

143. Ncgc00254294-01

144. Ncgc00259334-01

145. Ac-34535

146. As-14309

147. Sbi-0206946.p001

148. Butyl 4-hydroxybenzoate, >=99.0% (gc)

149. Ds-010619

150. Ab00513951

151. B3771

152. Ft-0623315

153. H0210

154. A16382

155. Butyl Parahydroxybenzoate [ep Impurity]

156. Butyl Parahydroxybenzoate [ep Monograph]

157. D01420

158. Ab00513951_09

159. A844895

160. Q3302873

161. Sr-01000389296-1

162. Sr-01000389296-3

163. W-100204

164. Brd-k08287586-001-03-6

165. Brd-k08287586-001-08-5

166. Butyl 4-hydroxybenzoate, Saj First Grade, >=99.0%

167. Propyl Hydroxybenzoate Impurity D [ep Impurity]

168. Z291799028

169. Methyl Parahydroxybenzoate Impurity D [ep Impurity]

170. 4-hydroxybenzoic Acid-n-butyl Ester 100 Microg/ml In Methanol

171. 4-hydroxybenzoic Acid-n-butyl Ester 100 Microg/ml In Acetonitrile

172. 4-hydroxybenzoic Acid-n-butyl Ester 1000 Microg/ml In Methanol

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 194.23 g/mol
Molecular Formula C11H14O3
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass194.094294304 g/mol
Monoisotopic Mass194.094294304 g/mol
Topological Polar Surface Area46.5 Ų
Heavy Atom Count14
Formal Charge0
Complexity171
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

It is used as a pharyngeal antiseptic in combination with other parabens.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1090


5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Active Moiety
BUTYLPARABEN
5.1.2 FDA UNII
3QPI1U3FV8
5.1.3 Pharmacological Classes
Chemical Structure [CS] - Allergens
5.2 Absorption, Distribution and Excretion

By the oral route, parabens are rapidly absorbed, metabolized, and excreted. The metabolic reactions and conversions in mammals vary with the chain length of the ester, the animal species, route of administration, and quantity tested. The metabolism of parabens in humans appears to be most closely related to that of dogs. The rate of metabolite excretion appears to decrease with increasing molecular weight of the ester. /4-Hydroxybenzoates (Parabens)/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. v6 639


After butylparaben is intravenously infused into the dog, nonhydrolyzed butylparaben is found in brain, spleen, and pancreas. In liver, kidney, and muscle, it is immediately hydrolyzed to p-hydroxybenzoic acid. Six hours after oral administration of 1.0 g/kg to dogs, the peak plasma concentration of free and total butyl paraben (15 and 141 ug/cu cm) is reached. After 48 hr, butylparaben is eliminated.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. v6 672


Skin penetration of methyl, ethyl, propyl and butyl parabens through excised guinea pig dorsal skin was examined, and effects of the penetration enhancers, l-menthol plus ethanol itself and N-dodecyl-2-pyrrolidone, were observed. Permeability of coefficients of the parabens correlated with n-octanol/water partition coefficients. Addition of 1% l-menthol in 15% ethanol about sixteen times increased the permeability coefficient of methyl paraben, whereas this enhancer decreased that of butyl paraben to about one fifth of the control value. A similar, though weaker, tendency was observed for the effects of 15% ethanol itself. 0.025% suspension of N-dodecyl-2-pyrrolidone increased the permeability coefficient of methyl paraben about seven times, whereas it did not change that of butylparaben significantly. Therefore, dependency of the permeability coefficients of the parabens on n-octanol/water partition coefficients almost disappeared in the presence of this compound. A spin label study with stratum corneum lipid liposomes revealed that increase of fluidity of the lipid bilayer by these penetration enhancers corresponded with their enhancement effects on skin penetration of methyl paraben. Perturbation of stratum corneum lipid lamella thus seems to be related with their enhancement of the absorption of hydrophilic paraben.

PMID:9301035 Kitagawa S et al; Chem Pharm Bull (Tokyo) 45 (8): 13454-7 (1997)


Intravenous (IV) injections at 50 mg/kg methylparaben, ethylparaben, propylparaben, or butylparaben were administered to groups of three or more fasted dogs. Similarly, these compounds were administered orally at a dose of 1.0 g/kg. Blood and urine were analyzed at predetermined intervals. Immediately following IV injection, very little ester remained in the blood. Metabolites were detectable in the blood up to 6 hr postinjection and 24 hr postingestion. Recovery of all esters but butylparaben ranged from 58 to 94% of the administered dose. Absorption was essentially complete. Recovery of butylparaben after oral administration was 40% and 48 after IV administration. The authors considered this finding a result of less effective hydrolysis of butylparaben. Dogs given 50 mg/kg were then killed and the distribution of esters and metabolites to organs was determined. Pure ester was recovered only in the brain, spleen, and pancreas. High concentrations of metabolites were detected in the liver and kidneys. With in vitro assays, it was found that esterases in the liver and kidneys of the dog were extremely efficient in hydrolyzing parabens --- complete hydrolysis after 3 minutes for all parabens except butylparaben, which took 30 to 60 minutes. No accumulation of parabens was observed in the tissues of dogs given orally 1 g/kg/day methylparaben or propylparaben for 1 year. The rate of urinary excretion of esters and metabolites in these dogs increased to such an extent that after 24 hr, 96 % of the dose was excreted in the urine. This is contrasted with dogs given a single dose of paraben in which the 96 % excretion level was not attained until 48 hr. When 10 % methylparaben or propylparaben in hydrophilic ointment was applied to the skin of a white rabbit for 48 h, esters and metabolites were not detected in the kidneys.

Cosmetic Ingredient Review; Final Amended Report on the Safety Assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in Cosmetic Products p 26. Int J Toxicol 27 Suppl 4: 1-82 (2008). Available from, as of November 21, 2016: https://online.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/PR427.pdf


For more Absorption, Distribution and Excretion (Complete) data for BUTYLPARABEN (9 total), please visit the HSDB record page.


5.3 Metabolism/Metabolites

In mice, rats, rabbits, or dogs, butyl paraben is excreted in the urine as unchanged benzoate, p-hydroxybenzoic acid, p-hydroxyhippuric acid (p-hydroxybenzoylglycine), ester glucuronides, ether glucuronides, or ether sulfates.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. v6 672


By the oral route, parabens are rapidly absorbed, metabolized, and excreted. The metabolic reactions and conversions in mammals vary with the chain length of the ester, the animal species, route of administration, and quantity tested. The metabolism of parabens in humans appears to be most closely related to that of dogs. The rate of metabolite excretion appears to decrease with increasing molecular weight of the ester. /4-Hydroxybenzoates (Parabens)/

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. v6 639


The penetration and metabolism of butylparaben using viable, full-thickness human skin /is described/. ... A total of 21% of the radiolabel penetrated to the receptor fluid after 24 hr. ... the principle metabolite, hydroxybenzoic acid, was detected in the receptor fluid, with barely detectable levels of butylparaben and no ethylparaben, in this study of full-thickness skin. ... This work was repeated to again examine the penetration and metabolism of butylparaben (0.4%) in an oil/water emulsion applied to the same full thickness viable human skin ... A finite dose (10 L/cm ) of the 2 emulsion was applied to the skin surface and remained in contact over a 24 hr period without occlusion. (14)C-butylparaben (labeled in the carbon ring) was measured in the receptor fluid. A mean value of 14.9% (+ or - 3.73%) of the radioactive label penetrated the full thickness human skin after 24 hr. The principle metabolite, hydroxybenzoic acid, was found in the receptor fluid (mean of 15.2% + or - 5.23%) of all 10 replications (skin donated from two individuals), but barely detectable levels of the parent butylparaben (mean of 0.225% 0.063%) were found only in 5 of 10 replications. The authors interpreted these results to confirm the near complete first-pass metabolism of butylparaben to p-hydroxybenzoic acid in human skin.

Cosmetic Ingredient Review; Final Amended Report on the Safety Assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in Cosmetic Products p 29. Int J Toxicol 27 Suppl 4: 1-82 (2008). Available from, as of November 21, 2016: https://online.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/PR427.pdf


... A study /was conducted/ of the in vitro dermal penetration and metabolism of methylparaben and butylparaben in rat and human skin. For each paraben, an oil in water emulsion with both radiolabeled ( C in the carbon 14 ring) and non-radiolabeled paraben was prepared to a target concentration (0.8% for methylparaben and 0.4% for butylparaben). Skin samples (10 replicates for rat skin and 13 replicates for human skin) were mounted in flow-through diffusion cells. Test emulsions were applied evenly at 10 L/cm , one time, with no occlusion. Samples of the receptor 2 fluid from a single skin were pooled, along with reference standards, were mixed with acetonitrile, filtered, and analyzed for methylparaben, butylparaben, and hydroxybenzoic acid using liquid chromatography coupled with mass spectroscopy. ... For Butylparaben, 52.3% was metabolized to hydroxybenzoic acid, with only 5.5% as unmetabolized butylparaben. Metabolism was different in human skin ... For butylparaben, 32.8% appeared as hydroxybenzoic acid and 49.7% as unmetabolized butylparaben.

Cosmetic Ingredient Review; Final Amended Report on the Safety Assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in Cosmetic Products p 28. Int J Toxicol 27 Suppl 4: 1-82 (2008). Available from, as of November 21, 2016: https://online.personalcarecouncil.org/ctfa-static/online/lists/cir-pdfs/PR427.pdf


For more Metabolism/Metabolites (Complete) data for BUTYLPARABEN (9 total), please visit the HSDB record page.


Butyl-4-hydroxybenzoate has known human metabolites that include (2S,3S,4S,5R)-6-(4-butoxycarbonylphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.

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


5.4 Biological Half-Life

BPB was rapidly cleared in hepatocytes from rat (t(1/2) = 3-4 min) and human (t(1/2) = 20-30 min).

PMID:22830980 Mathews JM et al; Xenobiotica 43 (2): 169-81 (2013)