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Also known as: Methyl 4-hydroxybenzoate, 99-76-3, Methyl paraben, Methyl p-hydroxybenzoate, Nipagin, Methyl parahydroxybenzoate

Molecular Formula

C₈H₈O₃

Molecular Weight

152.15 g/mol

InChI Key

LXCFILQKKLGQFO-UHFFFAOYSA-N

FDA UNII

A2I8C7HI9T

paraben is a natural product found in Zanthoxylum beecheyanum, Rhizophora apiculata, and other organisms with data available.

Methylparaben is a Standardized Chemical Allergen. The physiologic effect of methylparaben is by means of Increased Histamine Release, and Cell-mediated Immunity.

1 2D Structure

Methyl 4-Hydroxybenzoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl 4-hydroxybenzoate

2.1.2 InChI

InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3

2.1.3 InChI Key

LXCFILQKKLGQFO-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC(=O)C1=CC=C(C=C1)O

2.2 Other Identifiers

2.2.1 UNII

A2I8C7HI9T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-hydroxybenzoic Acid Methyl Ester

2. Methyl P-hydroxybenzoate

3. Methyl-4-hydroxybenzoate

4. Methylparaben, Sodium Salt

5. Nipagin

2.3.2 Depositor-Supplied Synonyms

1. Methyl 4-hydroxybenzoate

2. 99-76-3

3. Methyl Paraben

4. Methyl P-hydroxybenzoate

5. Nipagin

6. Methyl Parahydroxybenzoate

7. Tegosept M

8. Moldex

9. Maseptol

10. P-hydroxybenzoic Acid Methyl Ester

11. P-methoxycarbonylphenol

12. Benzoic Acid, 4-hydroxy-, Methyl Ester

13. P-carbomethoxyphenol

14. Preserval M

15. Methaben

16. Metoxyde

17. Preserval

18. Metaben

19. Paridol

20. Septos

21. Solbrol

22. Methyl Parasept

23. Methyl Butex

24. Methyl Chemosept

25. 4-hydroxybenzoic Acid Methyl Ester

26. Nipagin M

27. Aseptoform

28. Methylben

29. Abiol

30. Methyl-p-hydroxybenzoate

31. Methyl P-oxybenzoate

32. Solbrol M

33. 4-(methoxycarbonyl)phenol

34. 4-hydroxybenzoic Acid, Methyl Ester

35. Fema No. 2710

36. P-hydroxybenzoic Methyl Ester

37. Methyl Ester Of P-hydroxybenzoic Acid

38. P-oxybenzoesauremethylester

39. Mfcd00002352

40. Killitol

41. Benzoic Acid, P-hydroxy-, Methyl Ester

42. Methyl 4- Hydroxybenzoate

43. Nsc 3827

44. P-hydroxybenzoic Acid, Methyl Ester

45. Methylparaben E218

46. 4-hydroxy-benzoic Acid Methyl Ester

47. Nsc-3827

48. Methyl Paraben (e218)

49. Methylester Kyseliny P-hydroxybenzoove

50. Nsc-406127

51. A2i8c7hi9t

52. Chembl325372

53. Ins No.218

54. Chebi:31835

55. Ins-218

56. 4-hydroxybenzoic Acid-methyl Ester

57. Ncgc00159376-02

58. Ncgc00159376-04

59. E218

60. E-218

61. Dsstox_cid_2529

62. Wln: Qr Dvo1

63. Dsstox_rid_76616

64. Dsstox_gsid_22529

65. Methylparaben [usan]

66. Caswell No. 573pp

67. Fema Number 2710

68. 4-hydroxybenzoic Acid-methyl Ester 1000 Microg/ml In Acetonitrile

69. Cas-99-76-3

70. Smr000036660

71. Ccris 3946

72. Hsdb 1184

73. P-oxybenzoesauremethylester [german]

74. Einecs 202-785-7

75. Methylparaben [usan:nf]

76. Unii-a2i8c7hi9t

77. Epa Pesticide Chemical Code 061201

78. Brn 0509801

79. Metagin

80. Methyl4-hydroxybenzoate

81. Ai3-01336

82. Lexgard M

83. Paraben M

84. Methylester Kyseliny P-hydroxybenzoove [czech]

85. (methyl Paraben)

86. Methylparaben, Nf

87. Methylparaben, Fcc

88. 4-carbomethoxyphenol

89. Methylparaben (nf)

90. Methylparaben (tn)

91. Ins Number 218

92. Methylis Hydroxybenzoas

93. Solparol (salt/mix)

94. Methyl 4-hydoxybenzoate

95. Methyl 4 Hydroxybenzoate

96. Methyl 4-hydroxylbenzoate

97. Methyl 4-hydroxy-benzoate

98. Methyl-4-hydroxy-benzoate

99. Methyl 4-?hydroxybenzoate

100. Methylparaben [ii]

101. Methylparaben [mi]

102. Preserval Ms (salt/mix)

103. Bmse010009

104. Ec 202-785-7

105. Methyl (4-hydroxy)benzoate

106. Methylparaben [fcc]

107. Cid_7456

108. Schembl4440

109. Methylparaben [hsdb]

110. Methylparaben [inci]

111. Methylparaben [vandf]

112. Mls001304047

113. Mls001304187

114. Bidd:er0241

115. 4-hydroxybenzoate Methyl Ester

116. Methyl 4-hydroxybenzoate,(s)

117. Ins No. 218

118. Methyl Paraben [vandf]

119. Methylparaben [usp-rs]

120. Methylparaben [who-dd]

121. Amy901

122. Gtpl6273

123. Zinc1712

124. Methyl Parahydroxybenzoate (tn)

125. Dtxsid4022529

126. 4-hydroxybenzoic Acid Methylester

127. Methyl 4-hydroxybenzenecarboxylate

128. Nsc3827

129. Hms2883i08

130. Methyl Paraben, Analytical Standard

131. Methyl Parahydroxybenzoate (jp17)

132. 4-hydroxy Benzoic Acid Methyl Ester

133. Cs-d1181

134. Hy-n0349

135. Methyl Para Hydroxy Benzoate

136. Tox21_111616

137. Tox21_202318

138. Tox21_300009

139. Bbl005648

140. Bdbm50209100

141. Ck1194

142. Nsc406127

143. S3985

144. Stk802470

145. Akos000119910

146. Methyl Hydroxybenzoate [mart.]

147. Tox21_111616_1

148. Ccg-266228

149. Db14212

150. Methyl Hydroxybenzoate [who-ip]

151. Methyl P-hydroxybenzoate [fhfi]

152. Methyl Parahydroxybenzoate [jan]

153. Methyl 4-hydroxybenzoate, >=99%, Fcc

154. Ncgc00159376-03

155. Ncgc00159376-05

156. Ncgc00159376-06

157. Ncgc00253939-01

158. Ncgc00259867-01

159. Sy006626

160. Benzoic Acid,4-hydroxy,methyl Ester

161. Db-080628

162. Bb 0263150

163. E 218

164. Ft-0618697

165. Ft-0672044

166. H0216

167. M2206

168. Methyl 4-hydroxybenzoate, Analytical Standard

169. Methyl 4-hydroxybenzoate, P.a., 98-102%

170. Methylis Hydroxybenzoas [who-ip Latin]

171. D01400

172. Methyl 4-hydroxybenzoate, Usp, 98.0-102.0%

173. Methyl Parahydroxybenzoate [ep Monograph]

174. A846079

175. Methyl Salicylate Impurity C [ep Impurity]

176. Q229987

177. Q-200479

178. Methyl 4-hydroxybenzoate, Saj First Grade, >=98.0%

179. Methyl 4-hydroxybenzoate, Tested According To Ph.eur.

180. Propyl Hydroxybenzoate Impurity B [ep Impurity]

181. Z19674820

182. F1908-0119

183. Methyl 4-hydroxybenzoate, Bioxtra, >=99.0% (titration)

184. Methylparaben, Certified Reference Material, Tracecert(r)

185. 4-hydroxybenzoic Acid-methyl Ester 100 Microg/ml In Methanol

186. 4-hydroxybenzoic Acid-methyl Ester 1000 Microg/ml In Methanol

187. Methyl 4-hydroxybenzoate, Reagentplus(r), >=99.0%, Crystalline

188. Methylparaben, United States Pharmacopeia (usp) Reference Standard

189. Methyl 4-hydroxybenzoate, Bioreagent, Suitable For Insect Cell Culture

190. Methyl Parahydroxybenzoate, European Pharmacopoeia (ep) Reference Standard

191. Methylparaben, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₈H₈O₃
Molecular Weight	152.15 g/mol
XLogP3	2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	152.047344113 g/mol
Monoisotopic Mass	152.047344113 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	11
Formal Charge	0
Complexity	136
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Preservatives, Pharmaceutical

Substances added to pharmaceutical preparations to protect them from chemical change or microbial action. They include ANTI-BACTERIAL AGENTS and antioxidants. (See all compounds classified as Preservatives, Pharmaceutical.)

4.2 FDA Pharmacological Classification

4.2.1 Active Moiety

METHYLPARABEN

4.2.2 FDA UNII

A2I8C7HI9T

4.2.3 Pharmacological Classes

Chemical Structure [CS] - Allergens

4.3 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 methyl paraben is intravenously infused into the dog, nonhydrolyzed methyl paraben 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 methyl paraben (630 and 867 ug/cu cm) is reached. After 48 hr, the vast majority was 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 664

The excretion and metabolism of methylparaben were monitored in 6 preterm infants after they had received multiple doses of a gentamicin formulation containing paraben preservatives. The recovery of the paraben from urine averaged 82.6%. The urinary excretion ranged from 13.2 to 88.1%.

PMID:6631690 Hindmarsh KW et al; J Pharm Sci 72: 1039-41 (1983)

... a study /was conducted/ using human volunteers in which the levels of methylparaben in the stratum corneum were measured. Cosmetic emulsions containing 0.15, 0.25, and 0.5% (w/v) methylparaben were applied one time to the forearm (42 sq cm) of one male and one female subject. At 1, 2, 5, and 12 hr after application, a small area was cleaned of emulsion using wet cotton and methylparaben was extracted by application of a glass cylinder (3.1 sq cm) with 0.5 mL ethanol for 25 min. Methylparaben concentrations were determined in the ethanol solvent using HPLC (for the 1, 2, and 5 hr durations) and GC/MS for other treatments. ... For the single application, methylparaben reached its peak 1 - 2 hr after application (peak was slightly higher for each higher use concentration) and returned to baseline after 12 hr. /In another study,/ healthy Japanese adults (one male, eleven female) applied a lotion only (6 subjects) or a lotion and an emulsion (6 subjects) containing Methylparaben (concentration not stated) twice a day for 1 month. Concentrations of methylparaben in the stratum corneum were determined as above using GC/MS before the first application, at 1, 2, 3, and 4 weeks, and 2 days after stopping. ... Repeated applications resulted in an increase in methylparaben concentration in the stratum corneum over time for both the lotion application and the lotion plus emulsion application. After 2 days, methylparaben had returned to pretreatment levels.

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 25. 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 METHYLPARABEN (7 total), please visit the HSDB record page.

4.4 Metabolism/Metabolites

In mice, rats, rabbits, or dogs methylparaben 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 665

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

/This study examined/ the metabolic fate of methylparaben in rabbits. The compound was given by gastric intubation, and urine was analyzed by paper chromatography. Three major metabolites, p-hydroxybenzoic acid, p-hydroxyhippuric acid, and p-carboxyphenyl glucuronide, as well as two minor metabolites, p-hydroxybenzoyl glucuronide and p-carboxyphenyl sulfate, were identified. Rabbits given orally 0.4 or 0.8 g/kg methylparaben, ethylparaben, propylparaben, or butylparaben excreted only 0.2 to 0.9% of the unchanged ester by 24 hr. Urinary excretion of p-hydroxybenzoic acid was slower with increasing carbon chain length of the paraben alkyl group. Excretion of the conjugated acid was approximately that of the free acid. At 24 hr following paraben administration, 25 to 39% was recovered as p-hydroxybenzoic acid, 15 to 29% as the glycine conjugate, 5 to 8% as the ester glucuronide, 10 to 18% as the ether glucuronide, and 7 to 12% as the sulfate.

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 27. 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

The metabolism of methylparaben, ethylparaben, and propylparaben was studied in rats. Animals were given orally 100 mg of ester. Blood and urine were collected regularly and analyzed by paper chromatography. Paraben metabolites were identified in the urine 30 minutes after dosing. No unchanged paraben was detected. Ninety minutes after dosing, excretion of metabolites was maximum; thereafter, excretion decreased. p-Hydroxyhippuric acid appeared in the urine after 30 minutes; its concentration then increased evenly during the next 4 hr. The glucuronide and ethereal sulfate metabolites appeared only between 30 and 75 minutes postingestion. After 90 minutes, 67 to 75% of the total paraben dose was excreted as p-hydroxybenzoic acid, 10 to 12.5% as p-hydroxyhippuric acid, and 8 to 10% as glucuronyl derivatives. The concentration of free p-hydroxybenzoic acid in the blood remained extremely low. A continuous rise occurred within the first hour, but the concentration thereafter decreased and leveled off 1 to 2 hr after ingestion. The authors concluded that there were two stages of paraben detoxification: (1) absorption of paraben and excretion in urine of p-hydroxybenzoic acid, and (2) metabolic detoxification by glucuronic-, sulfo-, and glycino-conjugation.

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 27. 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 METHYLPARABEN (10 total), please visit the HSDB record page.

4.5 Mechanism of Action

...The mechanism of cytotoxic action of parabens may be linked to mitochondrial failure dependent on induction of membrane permeability transition accompanied by the mitochondrial depolarization and depletion of cellular ATP through uncoupling of oxidative phosphorylation.

PMID:12387298 Soni MG et al; Food Chem Toxicol 40 (10): 1335-73 (2002)

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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Methyl 4 Hydroxybenzoate

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ACTIVE PHARMA INGREDIENTS

2 API Suppliers

1 NDC API

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DEVELOPMENTS

1 Drugs in Development

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1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

10 BASF

1 Finar

1 Gangwal Chemicals

1 Kerry

1 Microlex e.U

1 Novo Excipients

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EXCIPIENTS BY APPLICATIONS

9 Solubilizers

8 Fillers, Diluents & Binders

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6 Topical

5 Direct Compression

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5 Granulation

4 Controlled & Modified Release

4 Film Formers & Plasticizers

2 Rheology Modifiers

2 Coating Systems & Additives

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1 Emulsifying Agents

1 Co-Processed Excipients

1 API Stability Enhancers

MARKET PLACE

2 APIs

6 EXCIPIENTS

REF. STANDARDS & IMPURITIES

1 USP

2 JP

1 Others

ANALYTICAL

1 Analytical Methods

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 38

MARKET PLACE

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

1DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

PATENTS & EXCLUSIVITIES

DIGITAL CONTENT

GLOBAL SALES INFORMATION

32 RELATED EXCIPIENT COMPANIES

62EXCIPIENTS BY APPLICATIONS

Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

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