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Chemistry

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Also known as: Propyl 4-hydroxybenzoate, 94-13-3, Propyl paraben, Propyl p-hydroxybenzoate, Nipasol, Nipazol

Molecular Formula

C₁₀H₁₂O₃

Molecular Weight

180.20 g/mol

InChI Key

QELSKZZBTMNZEB-UHFFFAOYSA-N

FDA UNII

Z8IX2SC1OH

propylparaben is a natural product found in Microtropis fokienensis, Soymida febrifuga, and other organisms with data available.

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

1 2D Structure

Propyl 4-Hydroxybenzoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

propyl 4-hydroxybenzoate

2.1.2 InChI

InChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3

2.1.3 InChI Key

QELSKZZBTMNZEB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCOC(=O)C1=CC=C(C=C1)O

2.2 Other Identifiers

2.2.1 UNII

Z8IX2SC1OH

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3(or 4)-hydroxybenzoic Acid Propyl Ester

2. 4-hydroxybenzoic Acid Propyl Ester

3. Bayer D 206

4. Nipazol

5. P-hydroxybenzoic Acid Propyl Ester

6. Peph

7. Propyl 4-hydroxybenzoate

8. Propyl P-hydroxybenzoate

9. Propylparaben, Monosodium Salt

2.3.2 Depositor-Supplied Synonyms

1. Propyl 4-hydroxybenzoate

2. 94-13-3

3. Propyl Paraben

4. Propyl P-hydroxybenzoate

5. Nipasol

6. Nipazol

7. Propyl Parahydroxybenzoate

8. 4-hydroxybenzoic Acid Propyl Ester

9. Propagin

10. Tegosept P

11. Nipagin P

12. N-propyl 4-hydroxybenzoate

13. Propyl Butex

14. Betacide P

15. Propylparasept

16. Chemacide Pk

17. Chemocide Pk

18. N-propyl P-hydroxybenzoate

19. Propyl Parasept

20. Aseptoform P

21. P-hydroxypropyl Benzoate

22. Propyl Chemosept

23. Protaben P

24. Propyl Aseptoform

25. Nipasol P

26. Solbrol P

27. 4-hydroxybenzoic Acid, Propyl Ester

28. Paseptol

29. Preserval P

30. Betacine P

31. Bonomold Op

32. Nipasol M

33. P-hydroxybenzoic Acid Propyl Ester

34. P-hydroxybenzoic Propyl Ester

35. Propyl-4-hydroxybenzoate

36. Parasept

37. N-propylparaben

38. Propyl Chemsept

39. Propyl-paraben

40. Benzoic Acid, 4-hydroxy-, Propyl Ester

41. N-propyl Paraben

42. Fema No. 2951

43. Benzoic Acid, P-hydroxy-, Propyl Ester

44. Paratexin P

45. Paraben P

46. Chemoside Pk

47. Lexgard P

48. Propyl Para-hydroxybenzoate

49. Pulvis Conservans

50. P-hydroxybenzoic Acid, Propyl Ester

51. Propylparaben E216

52. N-propyl-p-hydroxybenzoate

53. Nsc-8511

54. Propyl 4-oxidanylbenzoate

55. Nsc-23515

56. Z8ix2sc1oh

57. Mls002152934

58. Chebi:32063

59. 4-hydroxybenzoic Acid-propyl Ester

60. Nsc23515

61. P-hydroxybenzoic Acid N-propyl Ester

62. Ncgc00090965-03

63. Ncgc00090965-04

64. Smr000112070

65. Dsstox_cid_2527

66. Wln: Qr Dvo3

67. Dsstox_rid_76614

68. Dsstox_gsid_22527

69. Propyl Parahydroxybenzoate;propyl 4-hydroxybenzoate

70. Caswell No. 714

71. Propylparaben [usan]

72. Propyl 4-hydroxybenzoate, >=99%

73. Bayer D 206

74. Fema Number 2951

75. Pulvis Conservans (van)

76. 4-hydroxybenzoic Acid-propyl Ester 1000 Microg/ml In Acetonitrile

77. Cas-94-13-3

78. Hsdb 203

79. P-oxybenzoesaurepropylester [german]

80. Einecs 202-307-7

81. Unii-z8ix2sc1oh

82. Mfcd00002354

83. Nsc 23515

84. P-oxybenzoesaurepropylester

85. Propylparaben [usan:nf]

86. Epa Pesticide Chemical Code 061203

87. 4-hydroxybenzoic Acid-propyl Ester D7 (propyl D7)

88. Brn 1103245

89. Ai3-01341

90. Propylester Kyseliny P-hydroxybenzoove [czech]

91. 4-hydroxybenzoic Acid Propylester

92. (propyl Paraben)

93. 36m

94. Propylparaben (nf)

95. Propylester Kyseliny P-hydroxybenzoove

96. Propylparaben-[d7]

97. Propylparaben, Usan

98. Propylis Hydroxybenzoas

99. 85403-59-4

100. Propyl 4-?hydroxybenzoate

101. Schembl977

102. Propylparaben [ii]

103. Propylparaben [mi]

104. P-oxybenzoesaeurepropylester

105. Ec 202-307-7

106. Propylparaben [fcc]

107. Cid_7175

108. N-propyl-p-hydroxy-benzoate

109. Propylparaben [hsdb]

110. Propylparaben [inci]

111. Propylparaben [vandf]

112. 4-10-00-00374 (beilstein Handbook Reference)

113. Mls002222346

114. Mls006011654

115. Bidd:er0229

116. Propyl-4-hydroxybenzoate,(s)

117. Propyl Paraben [vandf]

118. Propylparaben [usp-rs]

119. Propylparaben [who-dd]

120. Chembl194014

121. Propyl Parahydroxybenzoate (tn)

122. Dtxsid4022527

123. Bdbm70190

124. Nsc8511

125. Hms2268k21

126. Propyl 4-hydroxybenzoate, Bioxtra

127. Propyl (4-hydroxybenzoate)

128. Propyl Parahydroxybenzoate (jp17)

129. Hy-n2026

130. Propyl Para Hydroxy Benzoate

131. Zinc1586788

132. Tox21_111048

133. Tox21_400012

134. Bbl023754

135. S5405

136. Stl294815

137. 4-hydroxybenzoic Acid, N-propyl Ester

138. Akos008948099

139. Component Of Heb-cort Mc (salt/mix)

140. Propyl Hydroxybenzoate [mart.]

141. Ccg-266432

142. Db14177

143. Ds-3427

144. Propyl Hydroxybenzoate [who-ip]

145. Propyl P-hydroxybenzoate [fhfi]

146. Propyl Parahydroxybenzoate [jan]

147. Ncgc00090965-01

148. Ncgc00090965-02

149. Ncgc00090965-05

150. Ncgc00090965-06

151. Ncgc00090965-07

152. Ac-34533

153. E216

154. Cs-0018518

155. Ft-0618698

156. H0219

157. P1955

158. Propylis Hydroxybenzoas [who-ip Latin]

159. D01422

160. Propyl Parahydroxybenzoate [ep Impurity]

161. Propyl Parahydroxybenzoate [ep Monograph]

162. A844839

163. Propyl 4-hydroxybenzoate, P.a., 99.0-100.5%

164. Propyl Parahydroxybenzoate 0.01 Mg/ml In Methanol

165. Propyl Parahydroxybenzoate 1.0 Mg/ml In Methanol

166. Q511627

167. 4-arm Peg-oms, 95%, Average M.w. 20,000

168. Q-201635

169. Propyl 4-hydroxybenzoate, Saj First Grade, >=98.0%

170. Propyl 4-hydroxybenzoate, Tested According To Ph.eur.

171. Propyl 4-hydroxybenzoate, Vetec(tm) Reagent Grade, 98%

172. Methyl Parahydroxybenzoate Impurity C [ep Impurity]

173. Propylparaben, Certified Reference Material, Tracecert(r)

174. 4-hydroxybenzoic Acid-propyl Ester 1000 Microg/ml In Methanol

175. 4-hydroxybenzoic Acid-propyl Ester 100 Microg/ml In Acetonitrile

176. Propylparaben, United States Pharmacopeia (usp) Reference Standard

177. Propyl Parahydroxybenzoate, European Pharmacopoeia (ep) Reference Standard

178. Propylparaben, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₂O₃
Molecular Weight	180.20 g/mol
XLogP3	3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	180.078644241 g/mol
Monoisotopic Mass	180.078644241 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	13
Formal Charge	0
Complexity	160
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 Drug and Medication Information

4.1 Therapeutic Uses

/EXPTL THER/ /The authors/ studied the prophylactic effect of propylparaben on alveolitis sicca dolorosa (ASD). Each of 45 patients received three tablets containing 33 mg Propylparaben or a placebo in the socket immediately after removal of a mandibular third molar. None of the patients receiving propylparaben developed ASD, whereas 24 percent of the placebo group did. The prophylatic effect of propylparaben was highly significant, and no side effects to treatment were reported.

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 66. 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

4.2 Drug Indication

Propylparaben is used in allergenic testing.

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

PROPYLPARABEN

5.2.2 FDA UNII

Z8IX2SC1OH

5.2.3 Pharmacological Classes

Chemical Structure [CS] - Allergens

5.3 Absorption, Distribution and Excretion

Systemic exposure to parabens in the neonatal population, in particular propyl-parabens (PPB), remains a concern. Blood concentrations and kinetics of methyl-parabens (MPB) and PPB were therefore determined in neonates receiving medicines containing these excipients. A multi-center, non-interventional, observational study of excipient-kinetics in neonates. 'Dried Blood Spot' samples were collected opportunistically at the same time as routine samples and the observations modelled using a non-linear mixed effects approach. A total of 841 blood MPB and PPB concentration data were available for evaluation from 181 pre- and term-neonates. Quantifiable blood concentrations of MPB and PPB were observed in 99% and 49% of patients, and 55% and 25% of all concentrations were above limit of detection (10 ng/mL), respectively. Only MPB data was amenable to modelling. Oral bioavailability was influenced by type of formulation and disposition was best described by a two compartment model with clearance (CL) influenced by post natal age (PNA); CL PNA<21 days 0.57 versus CL PNA>21 days 0.88 L/hr. Daily repeated administration of parabens containing medicines can result in prolonged systemic exposure to the parent compound in neonates. Animal toxicology studies of PPB that specifically address the neonatal period are required before a permitted daily exposure for this age group can be established.

PMID:25236342 Mulla H et al; Pharm Res 32 (3): 1084-93 (2015)

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. /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 propyl paraben is intravenously infused into the dog, unhydrolyzed propyl paraben is found only in the brain. 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 propyl paraben (205 and 370 ug/cu cm) is reached. After 48 hr, all propyl paraben 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 665

Parabens are in widespread use as preservatives in drugs. In the late 1990s, concerns were raised about their capacity to disrupt endocrine function based on in vitro data and in vivo uterotrophic tests. Studies in juvenile male rats provided conflicting results on pospubertal sperm production. In an exploratory pharmacokinetic study, Wistar male rats received a single dose of propylparaben (PP) at 3, 10, 100, or 1000 mg/kg, orally on postnatal day (PND) 31. Plasma PP concentrations were quantifiable up 8 hr after dosing with a mean T max value of 15 min. Distribution was 4.8 L/kg, the plasma elimination half-life was 47 min, and clearance was 4.20 (L/hr)/kg at 10 mg/kg. A sulfoconjugated metabolite was detected. In the juvenile toxicology study, PP was orally administered by gavage to 20 Wistar male rats at doses of 3, 10, 100, or 1000 mg/kg/day in 1% hydroxyethylcellulose for 8 weeks starting on PND21. A first subgroup of 10 males/dose was necropsied immediately after the 8-week exposure period; a second subgroup of 10 males/dose was necropsied after a 26-week washout period. Blood samples were taken from additional satellite animals after dosing on PND21 and PND77 for toxicokinetic analysis. There was no evidence of an effect of PP on the weight of the male reproductive organs, epididymal sperm parameters, hormone levels, or histopathology. The dose of 1000 mg/kg/day was the no-observed adverse effect level, corresponding to a maximum plasma concentration of 12,030 ng/mL and exposure to 47 760 ng x hr/mL (AUC0-8 hr) at the end of the treatment.

PMID:24068675 Gazin V et al; Toxicol Sci 136 (2): 392-401 (2013)

For more Absorption, Distribution and Excretion (Complete) data for PROPYLPARABEN (7 total), please visit the HSDB record page.

5.4 Metabolism/Metabolites

In mice, rats, rabbits, or dogs, propyl 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 670

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

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. ... 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.

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

Propyl-4-hydroxybenzoate has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(4-propoxycarbonylphenoxy)oxane-2-carboxylic acid.

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

5.5 Biological Half-Life

Propylparaben was administered orally to sexually immature rainbow trout every second day for up to 10 days in doses between 7 and 1830 mg/kg/2 days and in the water at 50 and 225 ug/L for 12 days. ... Half lives for propylparaben were 8.6 hr in liver and 1.5 hr in muscle.

PMID:15012902 Bjerregaard P et al; Comp Biochem Physiol C Toxicol Pharmacol 136 (4): 309-17 (2003)

5.6 Mechanism of Action

...The mechanism of propyl paraben 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:11346481 Soni MG et al; Food Chem Toxicol 39 (6): 513-32 (2001)

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About the Company : Jai Radhe Sales was founded in 1999 as an out-of-the-box distribution firm specializing in the global supply of high-quality pharmaceutical ingredients. The firm provides complete ...

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API Reference Price

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GROUP","customerCountry":"INDIA","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"3786.1","totalValueFC":"2258.5","currency":"INR","unitRateINR":"3795.5","date":"11-Oct-2024","totalValueINR":"189776.14","totalValueInUsd":"2258.5","indian_port":"JNPT","hs_no":"29182990","bill_no":"6067684","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"ROTTERDAM","supplierAddress":"Frankfurter Strasse 250, 64293 Darm stadt,(BENEFICIARY MERCKFINANCIALS SERVICES GMBH) GERMANY","customerAddress":"50A , RING ROAD,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1728844200,"product":"PROPYL 4-HYDROXYBENZOATE EMPROVE ESSENTIAL PH EUR,BP,JP,NF4PCS X 25KG","address":"50A , RING ROAD,","city":"BANGALORE, KARNATAKA","supplier":"MERCK LIFE SCIENCE KGAA","supplierCountry":"GERMANY","foreign_port":"ROTTERDAM","customer":"MERCK 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GROUP","customerCountry":"INDIA","quantity":"15.00","actualQuantity":"15","unit":"KGS","unitRateFc":"5595.1","totalValueFC":"1001.3","currency":"INR","unitRateINR":"5609.1","date":"26-Oct-2024","totalValueINR":"84136.95","totalValueInUsd":"1001.3","indian_port":"Bombay Air","hs_no":"29182990","bill_no":"6350918","productDescription":"API","marketType":"REGULATED MARKET","country":"GERMANY","selfForZScoreResived":"Pharma Grade","supplierPort":"FRANKFURT\/MAIN INT\\'L","supplierAddress":"Frankfurter Strasse 250, 64293 Darm stadt,(BENEFICIARY MERCKFINANCIALS SERVICES GMBH) GERMANY","customerAddress":"50A , RING ROAD,"}]

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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Propyl 4-Hydroxybenzoate

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ACTIVE PHARMA INGREDIENTS

1 API Suppliers

1 NDC API

1 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

1 Drugs in Development

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc

2 DKSH

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3 Actylis

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10 BASF

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2 Gangwal Chemicals

1 Kerry

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1 Novo Excipients

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EXCIPIENTS BY APPLICATIONS

9 Solubilizers

8 Fillers, Diluents & Binders

8 Parenteral

7 Thickeners and Stabilizers

6 Topical

5 Granulation

5 Direct Compression

4 Controlled & Modified Release

4 Coating Systems & Additives

4 Film Formers & Plasticizers

2 Rheology Modifiers

2 Disintegrants & Superdisintegrants

2 Taste Masking

1 Emulsifying Agents

1 Co-Processed Excipients

1 API Stability Enhancers

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7 EXCIPIENTS

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1 USP

1 JP

2 Others

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API REF. PRICE (USD/KG)

$ 50

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