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    Levomenol

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 151Xls

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    2D Structure
    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

    2D Structure

    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 Weight 222.37 g/mol
    Molecular Formula C15H26O
    XLogP33.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count4
    Exact Mass222.198365449 g/mol
    Monoisotopic Mass222.198365449 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity284
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.