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Chemistry

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Also known as: 120-51-4, Ascabiol, Benzoic acid benzyl ester, Benzoic acid, phenylmethyl ester, Benylate, Novoscabin

Molecular Formula

C₁₄H₁₂O₂

Molecular Weight

212.24 g/mol

InChI Key

SESFRYSPDFLNCH-UHFFFAOYSA-N

FDA UNII

N863NB338G

benzyl benzoate is a natural product found in Lonicera japonica, Populus tremula, and other organisms with data available.

1 2D Structure

Benzyl Benzoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

benzyl benzoate

2.1.2 InChI

InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2

2.1.3 InChI Key

SESFRYSPDFLNCH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

N863NB338G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acaril

2. Acarosan

3. Ansar

4. Antiscabiosum

5. Ascabiol

6. Benzanil

7. Benzemul

8. Benzylbenzoaat Smeersel Fna

9. Novoscabin

2.3.2 Depositor-Supplied Synonyms

1. 120-51-4

2. Ascabiol

3. Benzoic Acid Benzyl Ester

4. Benzoic Acid, Phenylmethyl Ester

5. Benylate

6. Novoscabin

7. Benzoic Acid, Benzyl Ester

8. Scabiozon

9. Scabitox

10. Scobenol

11. Ascabin

12. Phenylmethyl Benzoate

13. Benzyl Phenylformate

14. Benzylets

15. Colebenz

16. Peruscabin

17. Scabagen

18. Scabanca

19. Benzylbenzoate

20. Vanzoate

21. Scabide

22. Venzonate

23. Benzyl Benzenecarboxylate

24. Benzylis Benzoas

25. Benzyl Alcohol Benzoic Ester

26. Benzylbenzenecarboxylate

27. Benzylester Kyseliny Benzoove

28. Benzoic Acid Phenylmethylester

29. Fema No. 2138

30. Nsc 8081

31. Nsc-8081

32. Chembl1239

33. Antiscabiosum

34. Chebi:41237

35. N863nb338g

36. Ncgc00094981-03

37. Peruscabina

38. Dsstox_cid_9153

39. Benzylum Benzoicum

40. Dsstox_rid_78686

41. Dsstox_gsid_29153

42. Benzoesaeurebenzylester

43. Caswell No. 082

44. Venzoate

45. Fema Number 2138

46. Benzyl Benzoate, Analytical Standard

47. Benzyl Benzoate (natural)

48. Bzm

49. Cas-120-51-4

50. Smr000471875

51. Hsdb 208

52. Einecs 204-402-9

53. Benzylester Kyseliny Benzoove [czech]

54. Epa Pesticide Chemical Code 009501

55. Benzylbenzoat

56. Brn 2049280

57. Benzyl Benzoate [usp:jan]

58. Acarobenzyl

59. Benzevan

60. Bengal

61. Benzyl-benzoate

62. Unii-n863nb338g

63. Ai3-00523

64. 1dzm

65. Benylate (tn)

66. Benzoic Acid Benzyl

67. Mfcd00003075

68. Spectrum_001240

69. Benzoic Acid-benzyl Ester

70. Spectrum2_000532

71. Spectrum3_001757

72. Spectrum4_000773

73. Spectrum5_001128

74. Wln: Rvo1r

75. Benzyl Benzoate, >=99%

76. Ec 204-402-9

77. Schembl3038

78. Benzyl Benzoate [ii]

79. Benzyl Benzoate [mi]

80. Benzyl Benzoate Bp98

81. Bspbio_003494

82. Kbiogr_001186

83. Kbioss_001720

84. 4-09-00-00307 (beilstein Handbook Reference)

85. Mls001066412

86. Mls001336003

87. Mls001336004

88. Benzyl Benzoate [fcc]

89. Benzyl Benzoate [jan]

90. Benzyloxy Phenyl Ketone

91. Divk1c_000204

92. Spectrum1503002

93. Spbio_000543

94. Benzyl Benzoate (jp17/usp)

95. Benzyl Benzoate [fhfi]

96. Benzyl Benzoate [hsdb]

97. Benzyl Benzoate [inci]

98. Zinc1021

99. Benzyl Benzoate [mart.]

100. Dtxsid8029153

101. Benzoic Acid,benzyl Ester

102. Hms500k06

103. Kbio1_000204

104. Kbio2_001720

105. Kbio2_004288

106. Kbio2_006856

107. Kbio3_002714

108. Benzyl Benzoate [usp-rs]

109. Benzyl Benzoate [who-dd]

110. Benzyl Benzoate [who-ip]

111. Nsc8081

112. Ninds_000204

113. Hms1921p16

114. Hms2092f20

115. Hms2269d24

116. Pharmakon1600-01503002

117. Hy-b0935

118. Tox21_111372

119. Tox21_201337

120. Tox21_303418

121. Bdbm50134035

122. Ccg-39578

123. Nsc758204

124. S4599

125. Stl183088

126. Benzyl Benzoate [ep Impurity]

127. Benzyl Benzoate [orange Book]

128. Akos003495939

129. Benzyl Benzoate [ep Monograph]

130. Benzyl Benzoate [usp Impurity]

131. Benzyl Benzoate, >=99%, Fcc, Fg

132. Tox21_111372_1

133. Benzyl Benzoate [usp Monograph]

134. Db00676

135. Nsc-758204

136. Benzylis Benzoas [who-ip Latin]

137. Idi1_000204

138. Benzyl Benzoate, For Synthesis, 99.0%

139. Ncgc00094981-01

140. Ncgc00094981-02

141. Ncgc00094981-04

142. Ncgc00094981-05

143. Ncgc00094981-07

144. Ncgc00257502-01

145. Ncgc00258889-01

146. Ac-17033

147. Ls-14279

148. Sbi-0051748.p002

149. Db-041563

150. B0064

151. Ft-0622708

152. Benzyl Benzoate, Natural, >=99%, Fcc, Fg

153. Benzyl Benzoate, Reagentplus(r), >=99.0%

154. Benzyl Benzoate, Saj First Grade, >=98.0%

155. Benzyl Benzoate, Tested According To Ph.eur.

156. A14577

157. A19449

158. Benzyl Benzoate, Saj Special Grade, >=99.0%

159. D01138

160. Ab00052298_07

161. Benzyl Benzoate, Vetec(tm) Reagent Grade, 98%

162. Benzyl Benzoate, Meets Usp Testing Specifications

163. Q413755

164. Sr-01000763773

165. Benzoic Acid-benzyl Ester 5000 Microg/ml In Hexane

166. Q-200696

167. Sr-01000763773-2

168. Brd-k52072429-001-06-1

169. Benzoic Acid-benzyl Ester 100 Microg/ml In Acetonitrile

170. Benzoic Acid Benzyl Ester; Benzoic Acid Phenylmethyl Ester

171. Benzyl Benzoate, Certified Reference Material, Tracecert(r)

172. Benzyl Benzoate, United States Pharmacopeia (usp) Reference Standard

173. Benzyl Benzoate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₂O₂
Molecular Weight	212.24 g/mol
XLogP3	4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	4
Exact Mass	212.083729621 g/mol
Monoisotopic Mass	212.083729621 g/mol
Topological Polar Surface Area	26.3 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	213
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

Benzyl benzoate is used as an alternative agent for the topical treatment of scabies and also has been used for the topical treatment of pediculosis (lice infestation). ... Benzyl benzoate lotion, in an approximate concentration of 28% w/w, is applied topically. The drug should not be administered orally. Containers of the lotion should be shaken before using.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018

Scabicide, pediculicide.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 199

VET: Acaricide, pediculicide. Contraindicated in cats.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 199

4.2 Drug Warning

Studies in animals showed that oral ingestion of large doses of benzyl benzoate resulted in progressive incoordination, CNS excitation, seizures, and death.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018

When used in appropriate dosage, topically applied benzyl benzoate appears to have a low order of toxicity. Slight local irritation (especially of the male genitalia), itching, and allergic skin sensitivity may occur, and contact with the face, eyes, mucous membranes, and urethral meatus should be avoided. Repeated application of benzyl benzoate frequently causes contact dermatitis.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018

Benzyl benzoate is contraindicated in patients with a history of hypersensitivity to the drug.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018

Benzyl benzoate should not be applied to acutely inflamed skin or raw, weeping surfaces. If primary irritation or hypersensitivity occurs, treatment should be discontinued and the drug removed with soap and water.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018

VET: Cats are particularly susceptible to this action, and the use of benzyl benzoate in this species is therefore contraindicated. The most prominent feature is nervous excitability. The clinical signs resemble those of poisoning by benzoic acid.

Humphreys, D.J. Veterinary Toxicology. 3rd ed. London, England: Bailliere Tindell, 1988., p. 131

4.3 Drug Indication

Used to kill lice and the mites responsible for the skin condition scabies.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.

5.2 MeSH Pharmacological Classification

Insecticides

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P03 - Ectoparasiticides, incl. scabicides, insecticides and repellents

P03A - Ectoparasiticides, incl. scabicides

P03AX - Other ectoparasiticides, incl. scabicides

P03AX01 - Benzyl benzoate

5.4 Absorption, Distribution and Excretion

Absorption

No data are available on percutaneous absorption of benzyl benzoate. Some older studies have suggested some percutaneous absorption, however the amount was not quantified.

The maternal and fetal toxicity of benzyl benzoate, commonly used as antiparasitic insecticide, was evaluated in pregnant rats after a daily oral dose of 25 and 100 mg/kg. Biochemical, histopathological, and morphological examinations were performed. Dams were observed for maternal body weights and food and water consumption and subjected to caesarean section on (GD) 20. Maternal and fetal liver, kidney, heart, brain, and placenta were examined histopathologically under light microscope. Maternal and fetal liver and placenta were stained immunohistochemically for vascular endothelial growth factor (VEGF). Morphometric analysis of fetal body lengths, placental measurements, and fetal skeletal stainings was performed. Statistically significant alterations in biochemical parameters and placental and skeletal measurements were determined in treatment groups. In addition to histopathological changes, considerable differences were observed in the immunolocalization of VEGF in treatment groups. These results demonstrated that benzyl benzoate and its metabolites can transport to the placenta and eventually enter the fetuses.

PMID:21922633 Kockaya EA, Kilic A et al; Environ Toxicol 29 (1): 40-53 (2014)

The percutaneous absorption of benzyl benzoate measured in vivo in human and monkey studies. With the application sites occluded, 54% of the applied dose penetrated human skin in 24 hr compared with 69% absorption in the monkey skin.

PMID:2379896 Bronaugh RL et al; Food Chem Toxicol 28 (5): 369-74 (1990)

5.5 Metabolism/Metabolites

Rapidly hydrolyzed to benzoic acid and benzyl alcohol, which is further oxidized to benzoic acid. The benzoic acid is conjugated with glycine to form hippuric acid.

Converted to hippuric acid in vivo.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-203

5.6 Mechanism of Action

Benzyl benzoate exerts toxic effects on the nervous system of the parasite, resulting in its death. It is also toxic to mite ova, though its exact mechanism of action is unknown. In vitro, benzyl benzoate has been found to kill the Sarcoptes mite within 5 minutes.

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