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Menthyl Anthranilate
Also known as: Meradimate, 134-09-8, Meradimate [inn], Menthyl-o-aminobenzoate, (5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate, Anthranilic acid, p-menth-3-yl ester
Molecular Formula
C17H25NO2
Molecular Weight
275.4  g/mol
InChI Key
SOXAGEOHPCXXIO-UHFFFAOYSA-N
FDA UNII
J9QGD60OUZ

Meradimate, before known as menthyl anthranilate, is used in a maximal concentration of 5% in different products as a UV filter. It is currently required to be named as meradimate in all FDA approved OTC products. Meradimate is approved by the FDA and Health Canada to be used as an ingredient in sunblocking products.
1 2D Structure

Menthyl Anthranilate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate
2.1.2 InChI
InChI=1S/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3
2.1.3 InChI Key
SOXAGEOHPCXXIO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1CCC(C(C1)OC(=O)C2=CC=CC=C2N)C(C)C
2.2 Other Identifiers
2.2.1 UNII
J9QGD60OUZ
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. Meradimate

2. 134-09-8

3. Meradimate [inn]

4. Menthyl-o-aminobenzoate

5. (5-methyl-2-propan-2-ylcyclohexyl) 2-aminobenzoate

6. Anthranilic Acid, P-menth-3-yl Ester

7. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 2-aminobenzoate

8. 2-isopropyl-5-methylcyclohexyl 2-aminobenzoate

9. J9qgd60ouz

10. 5-methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate

11. Cyclohexanol,5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate)

12. Ncgc00159361-02

13. Dsstox_cid_27871

14. Dsstox_rid_82624

15. Dsstox_gsid_47895

16. Cas-134-09-8

17. Ccris 2468

18. Menthyl O-aminobenzoate

19. Einecs 205-129-8

20. Unii-j9qgd60ouz

21. Meradimate [usan:usp:inn]

22. Neo Heliopan Ma

23. Meradimate (usp/inn)

24. Meradimate [usan]

25. Menthyl Anthranilate, 98%

26. Meradimate [mart.]

27. Meradimate [usp-rs]

28. Meradimate [who-dd]

29. Schembl18884

30. 5-methyl-2-(1-methylethyl)cyclohexanol-2-aminobenzoate

31. Chembl1597075

32. Dtxsid3047895

33. Menthyl Anthranilate [mi]

34. Chebi:135974

35. Meradimate [usp Monograph]

36. Menthyl Anthranilate [inci]

37. Tox21_111602

38. Tox21_200561

39. Bbl028008

40. Stk083062

41. Akos001387784

42. Akos017278349

43. Db11096

44. Menthyl Anthranilate, Analytical Standard

45. Ncgc00159361-06

46. Ncgc00258115-01

47. Vs-08642

48. 2-aminobenzoic Acid P-menthane-3-yl Ester

49. Db-042217

50. Ft-0631778

51. D04927

52. Z262222228

53. 2-amino-benzoic Acid 2-isopropyl-5-methyl-cyclohexyl Ester

54. 2-aminobenzoic Acid (2-isopropyl-5-methyl-cyclohexyl) Ester

55. Meradimate, United States Pharmacopeia (usp) Reference Standard

56. Cyclohexanol, 5-methyl-2-(1-methylethyl)-, 1-(2-aminobenzoate)

57. Menthyl Anthranilate, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-07-29
3 Chemical and Physical Properties
Molecular Weight 275.4 g/mol
Molecular Formula C17H25NO2
XLogP35.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass275.188529040 g/mol
Monoisotopic Mass275.188529040 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count20
Formal Charge0
Complexity329
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count3
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Meradimate is used as an active ingredient in sunscreens or as a sunblock factor in different products. It fits under the category of broad-spectrum absorbent agent. These characteristics are important to consider due to the fact that this kind of ingredients can either absorb or reflect UV radiation. It is also important to know the type of rays that cover. UVA rays are the responsible of causing sun damage and reaching deeper layers of the skin while UVB can only cause sunburn in the outer layer of the skin. When an agent is of broad spectrum, this means that this agent is capable of acting in both UVA and UVB rays.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Meradimate effect provides a low-level, broad-spectrum protecting coverage effect.


5.2 Absorption, Distribution and Excretion

Absorption

Meradimate is not absorbed through the skin.


Route of Elimination

As meradimate is not absorbed, this pharmacokinetic property is not relevant.


Volume of Distribution

As meradimate is not absorbed, this pharmacokinetic property is not relevant.


Clearance

As meradimate is not absorbed, this pharmacokinetic property is not relevant.


5.3 Metabolism/Metabolites

As meradimate is not absorbed, this pharmacokinetic property is not relevant.


5.4 Biological Half-Life

As meradimate is not absorbed, this pharmacokinetic property is not relevant.


5.5 Mechanism of Action

Meradimate acts by absorbing both the UVA and UVB radiation, this provides this ingredient with a broad spectrum and it explains why it is highly used in different products such as lip balms, lipsticks, and moisturizers. Its protective effective action does not cover completely the UVA rays as it only reaches 336 nm. This has been proven even thought meradimate has a theoretical protective coverage range between 200-380 nm. Its function is related to the intrinsic structure of meradimate which is an ortho-disubstituted aminobenzoate. This structure allows easy electron delocalization and shifts in the maximum absorption.


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