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Chemistry

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Also known as: 65-85-0, Dracylic acid, Benzenecarboxylic acid, Carboxybenzene, Benzeneformic acid, Phenylformic acid
Molecular Formula
C7H6O2
Molecular Weight
122.12  g/mol
InChI Key
WPYMKLBDIGXBTP-UHFFFAOYSA-N
FDA UNII
8SKN0B0MIM

Benzoic Acid
A fungistatic compound that is widely used as a food preservative. It is conjugated to GLYCINE in the liver and excreted as hippuric acid.
Benzoic acid is a Nitrogen Binding Agent. The mechanism of action of benzoic acid is as an Ammonium Ion Binding Activity.
1 2D Structure

Benzoic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
benzoic acid
2.1.2 InChI
InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
2.1.3 InChI Key
WPYMKLBDIGXBTP-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
8SKN0B0MIM
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Benzoic

2. Benzoate, Potassium

3. Potassium Benzoate

4. Ucephan

2.3.2 Depositor-Supplied Synonyms

1. 65-85-0

2. Dracylic Acid

3. Benzenecarboxylic Acid

4. Carboxybenzene

5. Benzeneformic Acid

6. Phenylformic Acid

7. Benzenemethanoic Acid

8. Phenylcarboxylic Acid

9. Benzoate

10. Retardex

11. Benzoesaeure Gk

12. Benzoesaeure Gv

13. Retarder Ba

14. Tenn-plas

15. Acide Benzoique

16. Salvo Liquid

17. Solvo Powder

18. Benzoesaeure

19. Flowers Of Benzoin

20. Flowers Of Benjamin

21. Benzoic Acid, Tech.

22. Unisept Bza

23. Ha 1 (acid)

24. Kyselina Benzoova

25. Benzoic Acid (natural)

26. Benzoate (van)

27. Fema No. 2131

28. Ha 1

29. Benzoesaeure [german]

30. Caswell No. 081

31. Diacylic Acid

32. Oracylic Acid

33. Acide Benzoique [french]

34. Acido Benzoico [italian]

35. Benzenemethonic Acid

36. Kyselina Benzoova [czech]

37. Nsc 149

38. E 210

39. Vevovitall

40. Ccris 1893

41. Diacylate

42. Hsdb 704

43. Menno-florades

44. Benzoicum Acidum

45. Ai3-0310

46. Salvo, Liquid

47. Solvo, Powder

48. Ai3-03710

49. Phenyl Formic Acid

50. Epa Pesticide Chemical Code 009101

51. E210

52. Chebi:30746

53. Nsc-149

54. Aromatic Carboxylic Acid

55. Mfcd00002398

56. 8skn0b0mim

57. Benzoic Acid (e 210)

58. Ins No.210

59. Ins-210

60. Benzeneformate

61. Phenylformate

62. Benzenemethanoate

63. Phenylcarboxylate

64. Benzenecarboxylate

65. Benzoic Acid 100 Microg/ml In Acetone

66. Dsstox_cid_143

67. E-210

68. Dsstox_rid_75396

69. Dsstox_gsid_20143

70. Acido Benzoico

71. Carboxypolystyrene

72. Benzoic Acid [usan:jan]

73. Cas-65-85-0

74. Nsc7918

75. Benzoic Acid (tn)

76. Benzoic Acid Natural

77. Einecs 200-618-2

78. Unii-8skn0b0mim

79. Benzoic Acid [usp:jan]

80. Phenylcarboxy

81. Dracylate

82. Benzoic Aicd

83. Benzoic-acid

84. Bezoic Acid

85. Aromatic Acid

86. Benzenecarboxylic

87. Salvo Powder

88. Acidum Benzoicum

89. Benzoic- Acid

90. Retarder Bax

91. 1gyx

92. 1kqb

93. Benzoic Acid Usp

94. Sodium Benzoic Acid

95. Benzoic Acid,(s)

96. Natural Benzoic Acid

97. Benzoic Acid Solution

98. Benzoicacid-d5

99. Benzoic Acid-[13c7]

100. Wln: Qvr

101. Benzene-2-carboxylic Acid

102. Benzoic Acid-[18o2]

103. Benzoic Acid [ii]

104. Benzoic Acid [mi]

105. Benzoic Acid, Acs Reagent

106. Bmse000300

107. Chembl541

108. Epitope Id:139965

109. Ec 200-618-2

110. Benzoic Acid [fcc]

111. Benzoic Acid [jan]

112. Schembl1378

113. Benzoic Acid [fhfi]

114. Benzoic Acid [hsdb]

115. Benzoic Acid [inci]

116. Sampl4, O1

117. Benzoic Acid (jp17/usp)

118. Benzoic Acid [vandf]

119. Mls002415717

120. Benzoic Acid [mart.]

121. Bidd:er0597

122. Benzoic Acid [usp-rs]

123. Benzoic Acid [who-dd]

124. Benzoic Acid [who-ip]

125. Benzoic Acid, Ar, >=99%

126. Benzoic Acid, Lr, >=99%

127. Nsc149

128. Zinc1011

129. Benzoicum Acidum [hpus]

130. Dtxsid6020143

131. Fema 2131

132. Benzoic Acid (7ci,8ci,9ci)

133. Benzoic Acid, Analytical Standard

134. Benzoic Acid, P.a., 99.5%

135. Benzoic Acid [green Book]

136. Bdbm197302

137. Benzoic-2,3,4,5,6-d5 Acid

138. Hms2092f18

139. Hms2267d03

140. Hms3652b03

141. Pharmakon1600-01503001

142. Benzoic Acid [ep Monograph]

143. Hy-n0216

144. Tox21_202403

145. Tox21_300180

146. Benzoic Acid [usp Monograph]

147. Nsc758203

148. S4161

149. Stk301730

150. Benzoic Acid, Reagentplus(r), 99%

151. Akos000119619

152. Bs-3752

153. Ccg-213088

154. Db03793

155. Nsc-758203

156. Acidum Benzoicum [who-ip Latin]

157. Benzoic Acid, >=99.5%, Fcc, Fg

158. Benzoic Acid, Acs Reagent, >=99.5%

159. Ncgc00091886-01

160. Ncgc00091886-02

161. Ncgc00091886-03

162. Ncgc00254112-01

163. Ncgc00259952-01

164. Tiaprofenic Acid Impurity D [ep]

165. 5-isobenzofurancarboxylic Acid, 1,3-dihydro-1,3-dioxo-, Polymer With 1,3-isobenzofurandione And 1,1'-methylenebis[4-isocyanatobenzene], Reaction Products With Benzoic Acid

166. Benzoic Acid 1000 Microg/ml In Ethanol

167. Benzoic Acid, Usp, 99.5-100.5%

168. Bp-30148

169. Smr001252220

170. Sy009192

171. Benzoic Acid, Tested According To Ph.eur.

172. Sbi-0206720.p001

173. Benzoic Acid 100 Microg/ml In Acetonitrile

174. Benzoic Acid, Saj First Grade, >=99.5%

175. Db-029471

176. B0062

177. B2635

178. Cs-0008257

179. Ft-0622705

180. Ft-0662569

181. Ft-0662570

182. Ft-0770591

183. Sw219833-1

184. Benzoic Acid, Natural, >=99.5%, Fcc, Fg

185. Benzoic Acid, Saj Special Grade, >=99.5%

186. Benzoic Acid, Vetec(tm) Reagent Grade, 98%

187. Benzoic Acid, Meets Usp Testing Specifications

188. Benzoic Acid, Purified By Sublimation, >=99%

189. C00180

190. C00539

191. D00038

192. D85168

193. Mefenamic Acid Impurity D [ep Impurity]

194. Ab00949635_05

195. Ab00949635_06

196. Benzoic Acid 2000 Microg/ml In Dichloromethane

197. A835250

198. A934445

199. Benzoic Acid Zone Refined (number Of Passes:20)

200. Q191700

201. Sr-05000001919

202. Benzoic Acid, Puriss. P.a., Acs Reagent, 99.9%

203. Sr-05000001919-1

204. 0be368dc-6de6-4927-aecf-e4bb2968a4a0

205. Glycopyrronium Bromide Impurity D [ep Impurity]

206. Melting Point Standard 121-123c, Analytical Standard

207. Metronidazole Benzoate Impurity C [ep Impurity]

208. Z57127480

209. F2191-0092

210. Hydrous Benzoyl Peroxide Impurity B [ep Impurity]

211. Benzoic Acid, Nist(r) Srm(r) 39j, Calorimetric Standard

212. Benzoic Acid, Standard For Quantitative Nmr, Tracecert(r)

213. Methylaminolevulinate Hydrochloride Impurity I [ep]

214. Benzoic Acid, European Pharmacopoeia (ep) Reference Standard

215. Mettler-toledo Calibration Substance Me 18555, Benzoic Acid

216. Benzoic Acid On Polystyrene, 1.6-2.1 Mmol/g@crlfmfcd03456189

217. Benzoic Acid, For Calorimetrical Determination (approx. 26460 J/g)

218. Benzoic Acid, United States Pharmacopeia (usp) Reference Standard

219. Ss Benzoic Acid, 2000 Mug/ml In Dichloromethane, Analytical Standard

220. Benzoic Acid Solution, 200 Mug/ml In Methylene Chloride, Analytical Standard

221. Benzoic Acid Solution, Certified Reference Material, 2000 Mug/ml In Methylene Chloride

222. Benzoic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

223. Benzoic Acid, Puriss. P.a., Acs Reagent, Reag. Ph. Eur., >=99.9% (alkalimetric)

224. 14322-82-8

225. B A

226. Benzoic Acid, Certified Reference Material For Titrimetry, Certified By Bam According To Iso 17025, >=99.5%

227. Benzoic Acid, Meets Analytical Specification Of Ph. Eur., Bp, Usp, Fcc, E210, 99.5-100.5% (alkalimetric)

228. Carboxypolystyrene, 100-200 Mesh, Extent Of Labeling: 0.5-1.5 Mmol/g Loading, 1 % Cross-linked

229. Carboxypolystyrene, 100-200 Mesh, Extent Of Labeling: 1.6-3.0 Mmol/g Loading, 1 % Cross-linked

230. Mettler-toledo Calibration Substance Me 18555, Benzoic Acid, Analytical Standard, For The Calibration Of The Thermosystem 900, Traceable To Primary Standards (lgc)

231. Scavengepore(tm) Benzoic Acid, Macroporous, 40-70 Mesh, Extent Of Labeling: 0.5-1.5 Mmol Per G Loading

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 122.12 g/mol
Molecular Formula C7H6O2
XLogP31.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass122.036779430 g/mol
Monoisotopic Mass122.036779430 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count9
Formal Charge0
Complexity104
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

Antifungal Agents; Food Preservatives

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


Benzoic acid ... has a long history of use as an antifungal agent in topical therapeutic preparations such as Whitfield's ointment (benzoic acid 6% and salicylic acid 3%).

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 61


... It is used especially in the treatment of athlete's foot and to lesser extent for management of ringworm.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1172


Medication (vet): has been used with salicylic acid as topical antifungal

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 187


/Experimental Ther:/ Process for controlling waste nitrogen accumulation diseases in humans by administering at least 1 compound selected from group of benzoic acid, phenylacetic acid and their salts is disclosed. Sodium benzoate, (6.2 g/day) given to female patient with carbophosphate synthetase deficiency Increased total urinary nitrogen excretion 58%.

Brusilow SW et al; US Patent Number 4284647 08/18/81 (Johns Hopkins University)


4.2 Minimum/Potential Fatal Human Dose

The minimum lethal human oral dose of benzoic acid is 500 mg/kg body-weight.

Rowe, R.C., Sheskey, P.J., Quinn, M.E.; (Eds.), Handbook of Pharmaceutical Excipients 6th edition Pharmaceutical Press, London, England 2009, p. 62


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


Food Preservatives

Substances capable of inhibiting, retarding or arresting the process of fermentation, acidification or other deterioration of foods. (See all compounds classified as Food Preservatives.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
BENZOIC ACID
5.2.2 FDA UNII
8SKN0B0MIM
5.2.3 Pharmacological Classes
Nitrogen Binding Agent [EPC]; Ammonium Ion Binding Activity [MoA]
5.3 Absorption, Distribution and Excretion

After oral ingestion of benzoic acid and sodium benzoate, there is a rapid absorption (of undissociated benzoic acid) from the gastrointestinal tract in experimental animals or humans. ... 100% absorption can be assumed. In humans, the peak plasma concentration is reached within 1-2 hr.

International Programme on Chemical Safety's Concise International Chemical Assessment Documents. Number 26: Benzoic acid and Sodium Benzoate (2000). Available from, as of March 24, 2005: https://www.inchem.org/pages/cicads.html


Experiments on the distribution and elimination of (14)C-benzoate in the rat have shown no accumulation of sodium benzoate or benzoic acid in the body.

International Programme on Chemical Safety's Concise International Chemical Assessment Documents. Number 26: Benzoic acid and Sodium Benzoate (2000). Available from, as of March 24, 2005: https://www.inchem.org/pages/cicads.html


Benzoic acid and sodium benzoate are rapidly absorbed from the gastrointestinal tract of mammals and conjugated with glycine in the liver. The resulting hippuric acid is excreted in the urine rapidly (75% to 100% of the dose is excreted within 6 hours; the remaining dose is excreted within 2 to 3 days).

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology 20 (suppl. 3): 23-50 (2001)


/Investigators/ reported that 42.6% +/-16.5% of a dermally applied (14)C-Benzoic acid dose (4 ug/sq cm; in acetone) was excreted in the urine within 24 hours. When applied in petrolatum, 60.5% of the dose was absorbed.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology 20 (suppl. 3): 23-50 (2001)


For more Absorption, Distribution and Excretion (Complete) data for BENZOIC ACID (17 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

Benzoic acid ... conjugated with glycine to give hippuric acid in ... many mammals (man, monkeys, pig, rabbit, rodents, cat, dog, ferret & hedgehog). Dog, ferret, & hedgehog also excreted ... benzoyl glucuronide ... but indian fruit bat excreted almost all dose as benzoyl glucuronide.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 407


/Investigators/ demonstrated that biotransformation of benzoic acid to hippuric acid follows saturable or Michaelis-Menten kinetics in humans following ingestion of sodium benzoate. /Sodium Benzoate/

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology 20 (suppl. 3): 23-50 (2001)


The availability of glycine was the rate-limiting factor in the formation of hippuric acid. When insufficient glycine was available benzoyl glucuronide was formed.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology 20 (suppl. 3): 23-50 (2001)


/Investigators/ reported that both lipoic acid and valproic acid reduced the clearance of benzoic acid in rats that had been "loaded" with glycine. Both acids reduced the availability of hepatic coenzyme A that is needed for the adenosine triphosphate (ATP)-dependent conjugation with glycine.

Cosmetic Ingredient Review Expert Panel; International Journal of Toxicology 20 (suppl. 3): 23-50 (2001)


For more Metabolism/Metabolites (Complete) data for BENZOIC ACID (11 total), please visit the HSDB record page.


Benzoic acid has known human metabolites that include Benzoyl glucuronide.

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


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02-Jan-2021
31-Aug-2024
KGS
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