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Octocrylene

Octocrylene

Synopsis, Chemistry

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Also known as: 6197-30-4, 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, Octocrilene, 2-propenoic acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl ester, 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate, Octocrilene [inn]

Molecular Formula

C₂₄H₂₇NO₂

Molecular Weight

361.5 g/mol

InChI Key

FMJSMJQBSVNSBF-UHFFFAOYSA-N

FDA UNII

5A68WGF6WM

Octocrylene is a compound often used as an additive in sun screen, and is thought to have skin moisturizing effects because of its emollient properties. What makes this chemical such a popular additive to sun block, is its ability to neutralize UV radiation dissipated by sunlight, and to minimize skin damage from prolonged sun exposure. Octocrylene is also often combined with avobenzone, another common sunscreen ingredient often appearing on ingredient labels. Because of its effectiveness, the chemical has been approved across the globe for use in cosmetics and skin care products, but the concentrations of this ingredient are usually limited to no more than 10 or 12 percent. However, the use of this chemical doesnt just stop with sunscreen for face and arms, but can extend to a variety of other products, like hair spray, tannin oil, BB cream, conditioner, and CC cream, among others. Octocrylene may cause contact and photocontact allergy.

1 2D Structure

Octocrylene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate

2.1.2 InChI

InChI=1S/C24H27NO2/c1-3-5-12-19(4-2)18-27-24(26)22(17-25)23(20-13-8-6-9-14-20)21-15-10-7-11-16-21/h6-11,13-16,19H,3-5,12,18H2,1-2H3

2.1.3 InChI Key

FMJSMJQBSVNSBF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCC(CC)COC(=O)C(=C(C1=CC=CC=C1)C2=CC=CC=C2)C#N

2.2 Other Identifiers

2.2.1 UNII

5A68WGF6WM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate

2. 2-ethylhexyl 2-cyano-3,3-diphenylacrylate

2.3.2 Depositor-Supplied Synonyms

1. 6197-30-4

2. 2-ethylhexyl 2-cyano-3,3-diphenylacrylate

3. Octocrilene

4. 2-propenoic Acid, 2-cyano-3,3-diphenyl-, 2-ethylhexyl Ester

5. 2-ethylhexyl 2-cyano-3,3-diphenylprop-2-enoate

6. Octocrilene [inn]

7. 2-cyano-3,3-diphenylacrylic Acid 2-ethylhexyl Ester

8. 5a68wgf6wm

9. Mls002454364

10. Octocrilene (inn)

11. Nsc-760433

12. Parsol 340

13. Uv-3039

14. Ncgc00091585-03

15. Ncgc00091585-05

16. Smr001371988

17. Dsstox_cid_5299

18. Dsstox_rid_77734

19. 2-ethylhexyl 2-cyano-3,3-diphenylacrylate, 97%

20. Dsstox_gsid_25299

21. Octocrylene [usan]

22. Octocrileno

23. Octocrilenum

24. Octocrilenum [inn-latin]

25. Octocrileno [inn-spanish]

26. Uv Absorber-3

27. Cas-6197-30-4

28. Ccris 4814

29. Einecs 228-250-8

30. Octocrylene [usan:usp]

31. Unii-5a68wgf6wm

32. Octocrilen

33. 2-ethylhexyl 2-cyano-3,3-diphenyl-2-acrylate

34. 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate

35. Octocrylene (usp)

36. Neo Heliopan 303

37. Uvinul N539

38. 80135-31-5

39. 2-ethylhexyl 2-cyano-3,3-diphenyl-prop-2-enoate

40. Uvinul N-539

41. Octocrylene [mi]

42. 2-cyano-3,3-diphenyl-2-propenoic Acid, 2-ethylhexyl Ester

43. Octocrylene [inci]

44. Ec 228-250-8

45. Octocrilene [mart.]

46. Schembl16483

47. Octocrilene [who-dd]

48. Octocrylene [usp-rs]

49. Cid_22571

50. Octocrylene, Analytical Standard

51. Chembl1201147

52. Dtxsid9025299

53. Bdbm74416

54. Octocrylene [orange Book]

55. Chebi:135526

56. Hms3039d04

57. Octocrylene [usp Impurity]

58. Octocrylene [usp Monograph]

59. Amy40810

60. Bcp15293

61. Hy-a0087

62. Octyl 2-cyano-3,3-diphenylacrylate

63. Tox21_111153

64. Tox21_200236

65. Mfcd00059260

66. S1750

67. Akos015900539

68. Tox21_111153_1

69. Ac-7027

70. Ccg-268181

71. Cs-4296

72. Nsc 760433

73. Anthelios Sx Component Octocrylene

74. Ncgc00091585-01

75. Ncgc00091585-04

76. Ncgc00091585-06

77. Ncgc00257790-01

78. As-13821

79. Capital Soleil Component Octocrylene

80. 2-ethylhexyl 2-cyano-3,3-diphenyl-acrylate

81. 2-ethylhexyl Alpha-cyano-beta-phenylcinnamate

82. 2-ethylhexyl-alpha-cyano-beta-phenylcinnamate

83. Ft-0612234

84. Octocrylene Component Of Anthelios Sx

85. Octocrylene Component Of Capital Soleil

86. D05227

87. D70471

88. A833511

89. Q424805

90. Sr-01000864577

91. Q-201499

92. Sr-01000864577-2

93. 2-cyano-3,3-diphenyl-acrylic Acid 2-ethylhexyl Ester

94. 2-cyano-3,3-diphenylacrylic Acid-2-ethylhexyl Ester

95. 2-cyano-3,3-diphenyl-acrylic Acid 2-ethyl-hexyl Ester

96. (7-methoxy-8-(3-methyl-2-buten-1-yl)-2h-chromen-2-one)

97. Octocrylene, United States Pharmacopeia (usp) Reference Standard

98. Octocrylene, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₂₇NO₂
Molecular Weight	361.5 g/mol
XLogP3	7.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	10
Exact Mass	361.204179104 g/mol
Monoisotopic Mass	361.204179104 g/mol
Topological Polar Surface Area	50.1 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	510
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

In the US, Octocrylene has been evaluated by the FDA and is considered safe for use up to 10% in the formula. Similarly, the EU allows its use up to 10% in a formula while Health Canada allows a maximum use level of 12%.

5 Pharmacology and Biochemistry

5.1 Absorption, Distribution and Excretion

Absorption

Ecamsule is used topically, it not absorbed or metabolized.

Route of Elimination

Ecamsule is used topically, it not absorbed.

Volume of Distribution

Ecamsule is only used topically, it not absorbed.

Clearance

Ecamsule is used topically, it not absorbed or metabolized.

5.2 Metabolism/Metabolites

Ecamsule is used topically, it not absorbed.

5.3 Biological Half-Life

Ecamsule is only used topically, it does not have half life

5.4 Mechanism of Action

Octocrylene is an effective oil soluble liquid UVB filter. It has excellent dissolving properties for crystalline UV filters. Due to its outstanding photostability it is used as photostabilizer. Conjugated acrylate portion absorbs UVB and short-wave UVA (ultraviolet) rays with wavelengths in the range of 280-320 nm which protects the skin from direct DNA damage. The ethylhexanol portion is a fatty alcohol, which functions as an emollient due to it's hydrophobicity.

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