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Chemistry

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Also known as: 150-13-0, P-aminobenzoic acid, Paba, Para-aminobenzoic acid, Vitamin bx, Aminobenzoic acid
Molecular Formula
C7H7NO2
Molecular Weight
137.14  g/mol
InChI Key
ALYNCZNDIQEVRV-UHFFFAOYSA-N
FDA UNII
TL2TJE8QTX

4-Aminobenzoic Acid
An aminobenzoic acid isomer that combines with pteridine and GLUTAMIC ACID to form FOLIC ACID. The fact that 4-aminobenzoic acid absorbs light throughout the UVB range has also resulted in its use as an ingredient in SUNSCREENS.
Aminobenzoic acid is a Vitamin B Complex Member.
1 2D Structure

4-Aminobenzoic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-aminobenzoic acid
2.1.2 InChI
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
2.1.3 InChI Key
ALYNCZNDIQEVRV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
TL2TJE8QTX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4 Aminobenzoic Acid

2. 4 Aminobenzoic Acid, Potassium Salt

3. 4-aminobenzoate, Potassium

4. 4-aminobenzoic Acid, Potassium Salt

5. Aminobenzoate, Potassium

6. Aminobenzoic Acid (usp)

7. Epit Vit

8. Epitelplast

9. Hachemina

10. Magnesium Para-aminobenzoate

11. P Aminobenzoic Acid

12. P-aminobenzoic Acid

13. Paba

14. Pabasan

15. Para Aminobenzoic Acid

16. Para-aminobenzoate, Magnesium

17. Para-aminobenzoic Acid

18. Paraminan

19. Paraminol

20. Potaba

21. Potassium 4 Aminobenzoate

22. Potassium 4-aminobenzoate

23. Potassium Aminobenzoate

2.3.2 Depositor-Supplied Synonyms

1. 150-13-0

2. P-aminobenzoic Acid

3. Paba

4. Para-aminobenzoic Acid

5. Vitamin Bx

6. Aminobenzoic Acid

7. P-carboxyaniline

8. 4-carboxyaniline

9. Sunbrella

10. P-carboxyphenylamine

11. Hachemina

12. Paraminol

13. Benzoic Acid, 4-amino-

14. 1-amino-4-carboxybenzene

15. Pabacyd

16. Pabafilm

17. Pabamine

18. Paranate

19. Amben

20. Potaba

21. Romavit

22. Bacterial Vitamin H1

23. Vitamin H'

24. Anticanitic Vitamin

25. Chromotrichia Factor

26. Rvpaba Lipstick

27. Papacidum

28. Rvpaba

29. Trichochromogenic Factor

30. Anti-chromotrichia Factor

31. Super Shade By Coppertone

32. Benzoic Acid, P-amino-

33. Acidum Paraminobenzoicum

34. Benzoic Acid, 4-amino

35. Vitamin H1

36. Abee

37. Pabagel

38. Pabanol

39. 4-amino-benzoic Acid

40. Caswell No. 033b

41. Kyselina P-aminobenzoova

42. Mfcd00007894

43. P-aminobenzoesaeure

44. 4-aminobenzoesaeure

45. 4-carboxyphenylamine

46. Acido P-aminobenzoico

47. Pab

48. Gamma-aminobenzoic Acid

49. Aminobenzoate

50. Acido P-aminobenzoico [italian]

51. Kyselina P-aminobenzoova [czech]

52. Para-aminobenzoate

53. Anticantic Vitamin

54. 4-aminobenzoic-acid

55. Epa Pesticide Chemical Code 233300

56. Brn 0471605

57. P-amino Benzoic Acid

58. P-amino-benzoic Acid

59. Chebi:30753

60. Ai3-02436

61. Tl2tje8qtx

62. Nsc-7627

63. Aminobenzoic Acid (usp)

64. Aminobenzoic Acid [usp]

65. .gamma.-aminobenzoic Acid

66. Aniline-4-carboxylic Acid

67. Chembl542

68. Aminobenzoic Acid, Para

69. Benzoic Acid, 4-amino-, Homopolymer

70. Ncgc00091051-01

71. Dsstox_cid_4466

72. Dsstox_rid_77411

73. Dsstox_gsid_24466

74. 4-azaniumylbenzoate

75. 25136-77-0

76. Cas-150-13-0

77. Smr000471833

78. Ccris 6209

79. Hsdb 6840

80. Unii-tl2tje8qtx

81. Nsc 7627

82. Einecs 205-753-0

83. Actipol

84. P-carboxy Aniline

85. Amino Benzoic Acid

86. P-aminobezoic Acid

87. Gamma-aminobenzoate

88. 4-aminobezoic Acid

89. Trochromogenic Factor

90. Aniline-4-carboxylate

91. 4-amino Benzoic Acid

92. 4-(amino)benzoic Acid

93. Antichromotrichia Factor

94. Spectrum_000036

95. Rvpaba Lipstick (tn)

96. P-amino-benzoate

97. Spectrum2_000123

98. Spectrum3_000294

99. Spectrum4_000142

100. Spectrum5_000778

101. Paba [inci]

102. Tetracaine Ep Impurity A

103. P-aminobenzoic Acid,(s)

104. Bmse000066

105. Bmse000887

106. Bmse000916

107. Epitope Id:115017

108. Ec 205-753-0

109. Schembl8249

110. 4-aminobenzoic Acid, 99%

111. Oprea1_221096

112. Bspbio_001828

113. Kbiogr_000584

114. Kbioss_000396

115. Zinc920

116. Mls001066325

117. Mls001335919

118. Mls001335920

119. Para Amino Benzoic Acid Usp

120. Bidd:er0375

121. Divk1c_000783

122. Spbio_000166

123. 4-aminobenzoic Acid-[13c6]

124. P-aminobenzoic Acid, Free Acid

125. Component Of Presun (salt/mix)

126. Dtxsid6024466

127. Schembl13232108

128. Kbio1_000783

129. Kbio2_000396

130. Kbio2_002964

131. Kbio2_005532

132. Kbio3_001328

133. Nsc7627

134. P-aminobenzoic Acid [mi]

135. Aminobenzoic Acid [mart.]

136. Ninds_000783

137. P-aminobenzoic Acid 100g

138. Hms2269e10

139. Hms3870e13

140. Aminobenzoic Acid [usp-rs]

141. Aminobenzoic Acid [who-dd]

142. 4-aminobenzoic Acid [hsdb]

143. Act09225

144. Hy-b1008

145. Tox21_111069

146. Tox21_201702

147. Tox21_300087

148. Bdbm50145829

149. S4510

150. Stk397441

151. Para-aminobenzoic Acid [iarc]

152. Akos000118983

153. Para-aminobenzoic Acid [vandf]

154. Tox21_111069_1

155. Ac-8107

156. Am86626

157. Ccg-266139

158. Cs-4505

159. Db02362

160. Idi1_000783

161. 4-aminobenzoic Acid, Analytical Standard

162. Aminobenzoic Acid [usp Monograph]

163. Ncgc00091051-02

164. Ncgc00091051-03

165. Ncgc00091051-04

166. Ncgc00253923-01

167. Ncgc00259251-01

168. As-12493

169. Nci60_041683

170. Sy003749

171. 4-aminobenzoic Acid [ep Impurity]

172. Sbi-0051277.p003

173. 4-aminobenzoic Acid [ep Monograph]

174. Db-028695

175. 4-aminobenzoic Acid, Reagentplus(r), 99%

176. A0269

177. Ft-0617557

178. 4-aminobenzoic Acid, >=98.0% (hplc/nt)

179. 4-aminobenzoic Acid, Reagentplus(r), >=99%

180. C00568

181. D02456

182. A809010

183. Q284959

184. 4-aminobenzoic Acid, Vetec(tm) Reagent Grade, 98%

185. Q-200432

186. 4-aminobenzoic Acid, Purified By Sublimation, >=99%

187. Z57127446

188. 4-aminobenzoic Acid, 98.5-100.2%, Saj First Grade

189. 4-aminobenzoic Acid, Saj Special Grade, 99.5-100.2%

190. F2191-0259

191. Tetracaine Hydrochloride Impurity A [ep Impurity]

192. 4a5e7dd8-8a22-4642-86bf-05b778c0c78e

193. Procaine Benzylpenicillin Impurity A [ep Impurity]

194. 4-aminobenzoic Acid, European Pharmacopoeia (ep) Reference Standard

195. Aminobenzoic Acid, United States Pharmacopeia (usp) Reference Standard

196. Aminobenzoic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 137.14 g/mol
Molecular Formula C7H7NO2
XLogP30.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass137.047678466 g/mol
Monoisotopic Mass137.047678466 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count10
Formal Charge0
Complexity128
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

Sunscreening Agent

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Used orally in the treatment of conditions such as scleroderma, dermatomyositis, and Peyronie's disease, and topically as a sunscreen and protectant.

Hussar, D.A. (ed.). Modell's Drugs in Current Use and New Drugs. 38th ed. New York, NY: Springer Publishing Co., 1992., p. 91


Daily use of a sunscreen with a high SPF (greater than 15) on usually exposed skin is recommended for residents of areas of high ... /solar radiation/ who work outdoors or ... /enjoy/ regular outdoor recreation. Daily use of a sunscreen can reduce the cumulative ... /solar/ exposure that causes actinic keratoses and squamous-cell carcinoma.

IARC Working Group on the Evaluation of Cancer-Preventive Agents (2001) Sunscreens (IARC Handbooks of Cancer Prevention, Vol. 5), Lyon, IARC; Unit of Chemoprevention: Cancer-Preventive Effects of Sunscreens.


PABA has long been an accepted objective marker to verify completeness of 24 hour urine sampling as PABA is rapidly and almost completely eliminated with the urine. For this reason PABA has been used clinically for long as the indicator substance in pancreas and liver function tests.

European Commission Scientific Committeee on Consumer Products; Opinion on 4-Aminobenzoic acid (PABA), Available from, as of October 18, 2013: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_058.pdf


Sunscreen preparations should be applied uniformly and generously to all exposed skin surfaces, including lips, before exposure to UVB radiation. Two applications of the sunscreen may be needed for maximum protection. PABA-containing sunscreens are most effective when applied 1-2 hours before exposure to sunlight. Sunscreen products that are not water resistant should be reapplied after swimming, towel-drying, or profuse sweating and, because most sunscreens are easily removed from the skin, reapplication every 1-2 hours or according to the manufacturer's directions usually is required to provide adequate protection from UVB light. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


4.2 Drug Warning

PABA has been shown in vitro to displace methotrexate from plasma protein binding, thus increasing the free methotrexate concentrations.

Hansten P.D. Drug Interactions. 5th ed. Philadelphia: Lea and Febiger, 1985., p. 266


PABA derivatives reportedly have weak sensitization potential, but the incidence of allergic and photoallergic contact dermatitis associated with their use is increasing. Contamination of PABA derivatives with benzocaine which may cause allergic reactions has been reported. In patients allergic to compounds that are structurally similar to PABA (e.g., ester-type anesthetics, aniline dyes, thiazides, sulfonylurea and paraphenylenediamine drugs), cross-sensitivity to PABA derivatives has been reported occasionally; therefore, sunscreens containing PABA derivatives may be contraindicated in patients with a history of hypersensitivity to these chemicals.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


The manufacturers of sunscreen preparations with propellants warn that concentrating and subsequently inhaling the fumes from these preparations may be harmful or fatal. /Propellants/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


Because the absorptive characteristics of skin of children younger than 6 months of age may differ from those of adults and because the immaturity of metabolic and excretory pathways of these children may limit their ability to eliminate any percutaneously absorbed sunscreen agent, sunscreen products should be used in children younger than 6 months of age only as directed by a clinician. It is possible that the characteristics of geriatric skin also differ from those of skin in younger adults, but these characteristics and the need for special considerations regarding use of sunscreen preparations in this age group are poorly understood. /Sunscreens/

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


For more Drug Warnings (Complete) data for 4-AMINOBENZOIC ACID (13 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Active Moiety
AMINOBENZOIC ACID
5.1.2 FDA UNII
TL2TJE8QTX
5.1.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Vitamin B Complex Member
5.2 ATC Code

D - Dermatologicals

D02 - Emollients and protectives

D02B - Protectives against uv-radiation

D02BA - Protectives against uv-radiation for topical use

D02BA01 - Aminobenzoic acid


5.3 Absorption, Distribution and Excretion

The toxicokinetics of PABA is characterized by fast oral absorption, biotransformation by the major routes acetylation and glycine conjugation, the minor route by glucuronidation in the liver and kidney, and a fast and almost complete elimination via the urine within 24 hrs. PABA is extensively acetylated during percutaneous absorption in humans. Studies have shown that PABA can cross the placenta rapidly. Furthermore, the results of one study indicate that the human placenta has a significant capacity for acetylation of PABA.

European Commission Scientific Committeee on Consumer Products; Opinion on 4-Aminobenzoic acid (PABA), Available from, as of October 18, 2013: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_058.pdf


Of an oral dose of 1 g para-aminobenzoic acid, 82% was excreted in the urine of 3 male volunteers within 4 hr; para-aminohippuric acid and acetyl-para- aminohippuric acid were the principal metabolites. Concurrent administration of sodium benzoate totally abolished the excretion of these glycine conjugates.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 256 (1978)


The percutaneous absorption and metabolism of three structurally related compounds, benzoic acid, p-aminobenzoic acid (PABA), and ethyl aminobenzoate (benzocaine), were determined in vitro through hairless guinea pig skin. Benzocaine was also studied in human skin. Absorption of benzocaine was rapid and similar through both viable and nonviable skin. The absorption of the two acidic compounds, benzoic acid and PABA, was greater through nonviable skin. A small portion (6.9%) of absorbed benzoic acid was conjugated with glycine to form hippuric acid. Although N-acetyl-benzocaine had not been observed as a metabolite of benzocaine when studied by other routes of administration, both PABA and benzocaine were extensively N-acetylated during percutaneous absorption. Thus, the metabolism of these compounds should be considered in an accurate assessment of absorption after topical application.

PMID:2293213 Nathan D et al; Pharm Res 7(11): 1147-51(1990)


Skin absorption of PABA corresponding to 1.6 to 9.6% of the applied amount of PABA was measured in the urine of six male volunteers after application of PABA in three different preparations. No significant difference where observed between the three preparations.

European Commission Scientific Committeee on Consumer Products; Opinion on 4-Aminobenzoic acid (PABA), Available from, as of October 18, 2013: https://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_058.pdf


For more Absorption, Distribution and Excretion (Complete) data for 4-AMINOBENZOIC ACID (10 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

The two major metabolic pathways in a variety of species (guinea-pigs, rabbits and rats, but not dogs) are acetylation of the amino group and conjugation of the carboxy group, either with glycine or with glucuronic acid. Acetylation occurs in liver, heart, lung, blood and kidneys of rats and in the mucous membranes of the gastrointestinal tract of cattle. N-Acetyl-transferase activity in the presence of para-aminobenzoic acid is similar in liver and lung tissue of rabbits. Acetylation not only of para-aminobenzoic acid (30-40%) but also of para-aminohippuric acid (70%) takes place in the kidney of rabbits; acetylation of para-aminohippurate also occurs in the kidney of guinea-pigs.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 255 (1978)


Acetylation is dose-dependent. In rats given up to 5 mg/kg bw, 75% of the metabolites were acetylated; with higher doses, the extent of acetylation decreased down to 40%. An inverse relationship exists between acetylation and glycine conjugation: when acetylation decreases, glycine conjugation increases; such a decrease is seen in pantothenic acid-deficient rats. . Male rats excreted a larger amount of acetylated conjugates in the urine than females.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V16 255 (1978)


Following ingestion /in man/ of 1.0 g, ...main metabolites were p-aminohippuric acid and acetyl-p-aminohippuric acid.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 823


... PABA is predominantly metabolized by acetylation and glycine conjugation to form p-acetamidobenzoic acid (PAABA), p-aminohippuric acid (PAHA), and p-acetamidohippuric acid (PAAHA). ... The half-lives of PABA were 7.01 +/- 0.32 min in rapid acetylation rabbits and 7.08 +/- 0.78 min in slow acetylation rabbits. Significant differences were obtained in formation of PAABA and PAHA formed from PABA in both acetylation phenotype rabbits.

PMID:10594871 Song DJ et al; Biopharm Drug Dispos 20(5): 263-270 (1999)


For more Metabolism/Metabolites (Complete) data for 4-AMINOBENZOIC ACID (9 total), please visit the HSDB record page.


5.5 Biological Half-Life

... The half-lives of PABA were 7.01 +/- 0.32 min in rapid acetylation rabbits and 7.08+/-0.78 min in slow acetylation rabbits.

PMID:10594871 Song DJ et al; Biopharm Drug Dispos 20(5): 263-270 (1999)


5.6 Mechanism of Action

Radiation is absorbed by chemical sunscreens when the electron energy level of the drug is raised from its ground state to a higher energy level or excited state. Chromophore groups (C=C, C=O, O-N=O) with loosely held electrons are easily excited by radiation. Compounds which have several chromophore groups in optimal positions have high absorbance over a broad range of wavelengths. Chemical sunscreens are usually agents that absorb not less than 85% of UVB radiation (thus preventing burning) but may permit transmission of UVA radiation (thus allowing tanning). Some sunscreens may absorb wavelengths over a range that is slightly wider or narrower than that of UVB. All PABA derivatives absorb wavelengths of approximately 290-320 nm, benzophenone derivatives absorb wavelengths of approximately 250-360 nm, cinnamic acid derivatives absorb wavelengths of 280-320 nm, and salicylate derivatives and other miscellaneous chemical sunscreens absorb wavelengths of about 270-320 nm.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


The wavelength to which the skin is maximally sensitive had been accepted for many years to be 296.7 nm; however, recent evidence suggests that the most erythemogenic UVB wavelength may be slightly lower (e.g., somewhere in the range of 292-295 nm). In addition, of the stronger burning wavelengths that reach the earth's surface, most are approximately 310 nm. Therefore, sunscreens that maximally absorb UVB radiation near either of these wavelengths are particularly effective at preventing sunburn. Maximum absorbance occurs at about 290 nm for PABA, at about 295 nm for glyceryl-p-aminobenzoate, and at about 310 nm for the remaining PABA derivatives. Maximum absorbance occurs at 280-290 nm for benzophenone derivatives, at 310 nm for cinnamic acid derivatives with the exception of diethanolamine-p-methoxycinnamate which has its maximum absorbance at 290 nm, and at 300-305 nm for salicylate derivatives and other miscellaneous sunscreens.

American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013


Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.


Diminish the penetration of ultraviolet (UV) light through the epidermis by absorbing UV radiation within a specific wavelength range. The amount and wavelength of UV radiation absorbed are affected by the molecular structure of the sunscreen agent. /Sunscreen agents, topical/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006.


NDC API

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Antibody Engineering
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AMINOBENZOIC ACID

NDC Package Code : 12651-119

Start Marketing Date : 2020-03-05

End Marketing Date : 2024-12-31

Dosage Form (Strength) : POWDER (1kg/kg)

Marketing Category : BULK INGREDIENT

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08-Jan-2021
08-Oct-2024
KGS
overview
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Average Price (USD/KGS)

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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