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Levomenol

Levomenol

Synopsis, Chemistry

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Also known as: (-)-alpha-bisabolol, 23089-26-1, Alpha-bisabolol, Kamillosan, Bisabolol, Alpha-(-)-bisabolol

Molecular Formula

C₁₅H₂₆O

Molecular Weight

222.37 g/mol

InChI Key

RGZSQWQPBWRIAQ-CABCVRRESA-N

FDA UNII

24WE03BX2T

bisabolol is a natural product found in Santolina pectinata, Santolina villosa, and other organisms with data available.

1 2D Structure

Levomenol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

2.1.2 InChI

InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1

2.1.3 InChI Key

RGZSQWQPBWRIAQ-CABCVRRESA-N

2.1.4 Canonical SMILES

CC1=CCC(CC1)C(C)(CCC=C(C)C)O

2.1.5 Isomeric SMILES

CC1=CC[C@H](CC1)[C@](C)(CCC=C(C)C)O

2.2 Other Identifiers

2.2.1 UNII

24WE03BX2T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-4-epi-alpha-bisabolol

2. Bisabolol

3. Bisabolol, (+)-isomer

4. Bisabolol, (-)-isomer

2.3.2 Depositor-Supplied Synonyms

1. (-)-alpha-bisabolol

2. 23089-26-1

3. Alpha-bisabolol

4. Kamillosan

5. Bisabolol

6. Alpha-(-)-bisabolol

7. .alpha.-bisabolol

8. Levomenol [inn]

9. (-)-.alpha.-bisabolol

10. (-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol

11. Alpha-bisabolol (-)-form

12. Bisabolol, (-)-.alpha.

13. (2s)-6-methyl-2-[(1s)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

14. .alpha.-bisabolol, (-)-

15. Chebi:125

16. .alpha.-bisabolol (-)-form

17. 24we03bx2t

18. Fema No. 4666

19. (.alpha.s,1s)-.alpha.-bisabolol

20. 3-cyclohexene-1-methanol, A,4-dimethyl-a-(4-methyl-3-pentenyl)-,(as,1s)-

21. 3-cyclohexene-1-methanol, Alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (alphas,1s)-

22. Levomenolum

23. Kamilosan

24. ((-))-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol

25. (s)-6-methyl-2-((s)-4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol

26. 515-69-5

27. 1-alpha-bisabolol

28. Alpha-bisabolol, L-

29. Levomenolum [inn-latin]

30. Unii-24we03bx2t

31. Bisbalol

32. Ccris 9081

33. L-alpha-bisabolol

34. Levomenol, Inn

35. 3-cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, [s-(r*,r*)]-

36. (-)-a-bisabolol

37. Einecs 245-423-3

38. L-.alpha.-bisabolol

39. .alpha.-bisabolol, L-

40. Bisabolol [inci]

41. (-)- Alpha -bisabolol

42. .alpha.-(-)-bisabolol

43. Bisabolol [vandf]

44. Levomenol [mart.]

45. (-)--bisabolol

46. Alpha-(-)bisabolol

47. Levomenol [usp-rs]

48. Levomenol [who-dd]

49. Dsstox_cid_22094

50. Dsstox_rid_79924

51. Dsstox_gsid_42094

52. Schembl24989

53. Chembl1096927

54. Dtxsid4042094

55. (-)-(4s,8s)-alpha-bisabolol

56. Hy-n6967

57. Zinc1849759

58. [s-(r*,r*)]-.alpha.-bisabolol

59. Tox21_301375

60. 5-hepten-2-ol, 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-, (-)-

61. Bdbm50382730

62. Mfcd03412455

63. Nsc782530

64. Levomenol 100 Microg/ml In Methanol

65. Db13153

66. Lmpr0103060001

67. Nsc-782530

68. (-)-alpha-bisabolol, >=93% (gc)

69. (-)-alpha-bisabolol(-)-alpha-bisabolol

70. Ncgc00255987-01

71. (-)-alpha-bisabolol, Analytical Standard

72. .alpha.-bisabolol (-)-form [mi]

73. Cas-23089-26-1

74. Cs-0028206

75. Alpha-bisabolol 1000 Microg/ml In Isopropanol

76. C09621

77. Q179896

78. J-014978

79. (-)-alpha-bisabolol, Primary Pharmaceutical Reference Standard

80. Levomenol, United States Pharmacopeia (usp) Reference Standard

81. (-)-.alpha.-bisabolol (constituent Of Chamomile) [dsc]

82. 6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol, (-)-

83. 5-hepten-2-ol, 6-methyl-2-(4- Methyl-3-cyclohexen-1-yl), (-)-

84. [s-(r*,r*)]-.alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)cyclohex-3-ene-1-methanol

85. 3-cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-pentenyl)-, (-)-

86. 3-cyclohexene-1-methanol, Alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (.alpha.s,1s)-

87. Alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-(alphas,1s)-3-cyclohexene-1-methanol

88. 3-cyclohexene-1-methanol, .alpha.,4-dimethyl-.alpha.-(4-methyl-3-penten-1-yl)-, (.alpha.s,1s)-

89. 3-cyclohexene-1-methanol, Alpha,4-dimethyl-alpha-(4-methyl-3-pentenyl)-, (s-(theta,theta))-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₆O
Molecular Weight	222.37 g/mol
XLogP3	3.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	222.198365449 g/mol
Monoisotopic Mass	222.198365449 g/mol
Topological Polar Surface Area	20.2 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	284
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Drug Indication

Levomenol has been known to elicit a number of potentially beneficial pharmacological effects, including anti-irritant, anti-inflammatory, and anti-microbial actions. Bisabolol is also demonstrated to enhance the percutaneous absorption of certain molecules

5 Pharmacology and Biochemistry

5.1 Pharmacology

Levomenol is an anti-inflammatory and natural moisturizing agent that has been found to diminish the signs of photodamage, reduce pruritus, and ameliorate skin texture and elasticity.

5.2 Absorption, Distribution and Excretion

Absorption

The purpose of the present investigations was to study the cutaneous absorption of sesquiterpenic alcohol, the major active principle of chamomile. For these investigations 14C-labelled levomenol ((-)-6-methyl-2-(4-methyl-3-cyclohexen-1-yl)-5-hepten-2-ol; (-)-alpha-bisabolol) was prepared by biochemical incorporation of [14C]-acetate into the molecule. 5 h after topical application of the radiolabelled substance onto nude mice half of the radioactivity was found in the skin. The other part was measured in tissue and organes. 90% of this radioactivity was analysed as intact levomenol.

Volume of Distribution

To demonstrate the distribution of the substance in the skin a part of this tissue was cutted into horizontal slices by a cryotome. From the slices autoradiograms were produced. The densitometric measuration showed that there was a fast penetration of levomenol into the skin. 5 h after the topical application the substance was displaced from outermost to innermost areas. From these results a fast cutaneous absorption and a long therapeutical effect of the antiphlogistic and spasmolytic levomenol in the skin can be expected.