Homosalate

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Also known as: 118-56-9, Homomenthyl salicylate, 3,3,5-trimethylcyclohexyl salicylate, Coppertone, Heliopan, Heliophan

Molecular Formula

C₁₆H₂₂O₃

Molecular Weight

262.34 g/mol

InChI Key

WSSJONWNBBTCMG-UHFFFAOYSA-N

FDA UNII

V06SV4M95S

Homosalate is an organic compound that belongs to salicylates. It is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. Salicylates prevent direct skin exposure to the suns harmful rays by absorbing ultraviolet (UV) light. Homosalate specifically absorbs short-wave UVB rays, which are associated with DNA damage and increased risk of skin cancer. It is a common ingredient in many commercially available sunscreens. There are no reported adverse effects from homosalate.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3,3,5-trimethylcyclohexyl) 2-hydroxybenzoate

2.1.2 InChI

InChI=1S/C16H22O3/c1-11-8-12(10-16(2,3)9-11)19-15(18)13-6-4-5-7-14(13)17/h4-7,11-12,17H,8-10H2,1-3H3

2.1.3 InChI Key

WSSJONWNBBTCMG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1CC(CC(C1)(C)C)OC(=O)C2=CC=CC=C2O

2.2 Other Identifiers

2.2.1 UNII

V06SV4M95S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3,3,5-trimethylcyclohexyl Salicylate

2.3.2 Depositor-Supplied Synonyms

1. 118-56-9

2. Homomenthyl Salicylate

3. 3,3,5-trimethylcyclohexyl Salicylate

4. Coppertone

5. Heliopan

6. Heliophan

7. Eusolex

8. Filtersol ''a''

9. (3,3,5-trimethylcyclohexyl) 2-hydroxybenzoate

10. M-homomenthyl Salicylate

11. 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate

12. Homosalatum

13. Benzoic Acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl Ester

14. Nsc 164918

15. 2-hydroxybenzoic Acid 3,3,5-trimethylcyclohexyl Ester

16. Mfcd00019377

17. Salicylic Acid 3,3,5-trimethylcyclohexyl Ester

18. 52253-93-7

19. Nsc-164918

20. V06sv4m95s

21. Salicylic Acid, 3,3,5-trimethylcyclohexyl Ester

22. Ncgc00091888-01

23. Dsstox_cid_6241

24. Dsstox_rid_78073

25. Dsstox_gsid_26241

26. Salicylic Acid, 3,3,5-trimethylcyclohexyl Ester (8ci)

27. Caswell No. 482b

28. Homosalato

29. 3,3,5-trimethylcyclohexyl Salicylate (cis- And Trans- Mixture)

30. Filtrosol A

31. Homosalatum [inn-latin]

32. Homosalato [inn-spanish]

33. Ccris 4885

34. Component Of Coppertone

35. Sr-05000001884

36. Salicylic Acid, M-homomenthyl Ester

37. Metahomomenthyl Salicylate

38. Einecs 204-260-8

39. Epa Pesticide Chemical Code 076603

40. Unii-v06sv4m95s

41. Homosalat

42. Homosalate [usan:usp:inn]

43. Kemester Hms

44. Cas-118-56-9

45. Homosalate [mi]

46. Homosalate (usp/inn)

47. Homosalate [inn]

48. Prestwick1_001090

49. Prestwick2_001090

50. Prestwick3_001090

51. Homosalate [inci]

52. Homosalate [usan]

53. Ec 204-260-8

54. Homosalate [mart.]

55. Homosalate [usp-rs]

56. Homosalate [who-dd]

57. Schembl16207

58. Bspbio_001140

59. Spectrum1505020

60. Spbio_003030

61. Bpbio1_001254

62. Chembl1377575

63. Dtxsid1026241

64. Chebi:91642

65. Homosalate [usp Impurity]

66. 3,5-trimethylcyclohexyl Salicylate

67. Hms1571i22

68. Hms2093g22

69. Hms2098i22

70. Hms3715i22

71. Homosalate [usp Monograph]

72. Pharmakon1600-01505020

73. Component Of Coppertone (salt/mix)

74. Hy-b0928

75. Tox21_111174

76. Tox21_202109

77. Tox21_303082

78. Nsc164918

79. Nsc758908

80. S4572

81. Akos015904082

82. Tox21_111174_1

83. Ccg-213330

84. Db11064

85. Nsc-758908

86. Ncgc00091888-02

87. Ncgc00091888-03

88. Ncgc00091888-04

89. Ncgc00091888-05

90. Ncgc00091888-06

91. Ncgc00091888-09

92. Ncgc00257063-01

93. Ncgc00259658-01

94. As-10409

95. Sy051923

96. Sbi-0206787.p001

97. Ab00514041

98. Ft-0614020

99. Salicylic Acid,3,5-trimethylcyclohexyl Ester

100. T2278

101. Benzoic Acid, 3,3,5-trimethylcyclohexyl Ester

102. D04450

103. E78223

104. 2,3,3,4,4,5,5,6-octachlorobiphenyl

105. Ab00514041_02

106. A921433

107. J-519754

108. Q2260189

109. Sr-05000001884-1

110. Sr-05000001884-2

111. Brd-a34751532-001-03-6

112. Brd-a34751532-001-04-4

113. 2-hydroxybenzoic Acid (3,3,5-trimethylcyclohexyl) Ester

114. Homosalate, United States Pharmacopeia (usp) Reference Standard

115. 3,3,5-trimethylcyclohexyl Salicylate 100 Microg/ml In Acetonitrile

116. 3,3,5-trimethylcyclohexyl Salicylate 100 Microg/ml In Methanol

117. Homosalate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₂O₃
Molecular Weight	262.34 g/mol
XLogP3	5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	262.15689456 g/mol
Monoisotopic Mass	262.15689456 g/mol
Topological Polar Surface Area	46.5 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	324
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

As ingredient in many sunscreen for protection against sunburn, skin aging and skin cancer.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Acts as UV filters.

5.2 MeSH Pharmacological Classification

Sunscreening Agents

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)

5.3 Absorption, Distribution and Excretion

Absorption