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    Chemistry

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    Also known as: 89-83-8, 2-isopropyl-5-methylphenol, Thyme camphor, 5-methyl-2-isopropylphenol, 6-isopropyl-m-cresol, 5-methyl-2-(1-methylethyl)phenol
    Molecular Formula
    C10H14O
    Molecular Weight
    150.22  g/mol
    InChI Key
    MGSRCZKZVOBKFT-UHFFFAOYSA-N
    FDA UNII
    3J50XA376E
    Thymol
    A phenol obtained from thyme oil or other volatile oils used as a stabilizer in pharmaceutical preparations, and as an antiseptic (antibacterial or antifungal) agent.
    1 2D Structure

    Thymol

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-methyl-2-propan-2-ylphenol
    2.1.2 InChI
    InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3
    2.1.3 InChI Key
    MGSRCZKZVOBKFT-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=C(C=C1)C(C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    3J50XA376E
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Apiguard

    2.3.2 Depositor-Supplied Synonyms

    1. 89-83-8

    2. 2-isopropyl-5-methylphenol

    3. Thyme Camphor

    4. 5-methyl-2-isopropylphenol

    5. 6-isopropyl-m-cresol

    6. 5-methyl-2-(1-methylethyl)phenol

    7. Thymic Acid

    8. 3-p-cymenol

    9. Phenol, 5-methyl-2-(1-methylethyl)-

    10. P-cymen-3-ol

    11. 3-hydroxy-p-cymene

    12. 6-isopropyl-3-methylphenol

    13. Isopropyl Cresol

    14. 5-methyl-2-(propan-2-yl)phenol

    15. M-thymol

    16. Apiguard

    17. 5-methyl-2-propan-2-ylphenol

    18. 5-methyl-2-isopropyl-1-phenol

    19. 3-methyl-6-isopropylphenol

    20. 1-hydroxy-5-methyl-2-isopropylbenzene

    21. P-cymene, 3-hydroxy-

    22. M-cresol, 6-isopropyl-

    23. 1-methyl-3-hydroxy-4-isopropylbenzene

    24. 2-hydroxy-1-isopropyl-4-methylbenzene

    25. 6-isopropyl-p-cresol

    26. 2-isopropyl-5-methyl-phenol

    27. Fema No. 3066

    28. Phenol, 2-isopropyl-5-methyl-

    29. 3-hydroxy-1-methyl-4-isopropylbenzene

    30. Thymolum

    31. Nsc 11215

    32. Nsc-11215

    33. Nsc-47821

    34. Nsc-49142

    35. Chembl29411

    36. Chebi:27607

    37. 3j50xa376e

    38. Ncgc00159373-02

    39. Ncgc00159373-04

    40. Thymol (natural)

    41. Dsstox_cid_14972

    42. Dsstox_rid_79231

    43. Dsstox_gsid_34972

    44. Cymophenol, Alpha-

    45. Wln: Qr C1 Fy1&1

    46. Caswell No. 856a

    47. Fema Number 3066

    48. Cas-89-83-8

    49. Ccris 7299

    50. Hsdb 866

    51. Thymol [jan:nf]

    52. Einecs 201-944-8

    53. Epa Pesticide Chemical Code 080402

    54. Thymate

    55. Unii-3j50xa376e

    56. Ai3-00708

    57. Thymol, Puriss.

    58. Thymol & Propolis

    59. 5-methyl-2-(1-methylethyl)-phenol

    60. Mfcd00002309

    61. Thymol (tn)

    62. Thymol,(s)

    63. Thymol Crystal Puriss

    64. Thymol, Fcc, Fg

    65. Thymolum [hpus]

    66. Thymol (jp17/nf)

    67. Thymol [vandf]

    68. Thymol [fhfi]

    69. Thymol [hsdb]

    70. Thymol [inci]

    71. Thymol [fcc]

    72. Thymol [jan]

    73. Thymol [usp-rs]

    74. Thymol [who-dd]

    75. Thymol [ii]

    76. Thymol [mi]

    77. Thymol [mart.]

    78. Ec 201-944-8

    79. Thymol, Analytical Standard

    80. Thymol, >=98.5%

    81. Schembl22165

    82. Mls001074692

    83. Bidd:er0658

    84. Thymol [ep Monograph]

    85. Gtpl2499

    86. Dtxsid6034972

    87. 5-methyl-2-propan-2-yl-phenol

    88. 1e06

    89. Hms2267p15

    90. Zinc967597

    91. Hy-n6810

    92. Nsc11215

    93. Nsc47821

    94. Nsc49142

    95. Tox21_111613

    96. Tox21_300358

    97. Bbl011604

    98. Bdbm50240432

    99. S5157

    100. Stk397445

    101. Thymol, Tested According To Ph.eur.

    102. Akos000119786

    103. Tox21_111613_1

    104. Ccg-266209

    105. Db02513

    106. Ks-5170

    107. Lmpr0102090029

    108. Mb00129

    109. Thymol, Saj First Grade, >=98.0%

    110. 1-methyl-3-hydroxy-4-isopropyl Benzene

    111. Ncgc00159373-03

    112. Ncgc00159373-05

    113. Ncgc00254459-01

    114. Ac-34742

    115. Smr000471893

    116. Db-002030

    117. Cs-0008421

    118. Ft-0612711

    119. M0410

    120. C09908

    121. D01039

    122. Thymol, Primary Pharmaceutical Reference Standard

    123. A845314

    124. A861043

    125. Ae-562/43461428

    126. Q408883

    127. Sr-01000763796

    128. Sr-01000763796-2

    129. W-100357

    130. Thymol, Standard For Quantitative Nmr, Tracecert(r)

    131. Z57127464

    132. Benzene,2-hydroxy,1-isopropyl,4-methyl Thymol

    133. F0001-2201

    134. Thymol, European Pharmacopoeia (ep) Reference Standard

    135. Thymol, United States Pharmacopeia (usp) Reference Standard

    136. Thymol, Meets Analytical Specification Of Ph. Eur., Bp, Nf, 99-101%

    137. Thymol, Pharmaceutical Secondary Standard; Certified Reference Material

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 150.22 g/mol
    Molecular Formula C10H14O
    XLogP33.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count1
    Rotatable Bond Count1
    Exact Mass150.104465066 g/mol
    Monoisotopic Mass150.104465066 g/mol
    Topological Polar Surface Area20.2 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity120
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Anti-Infective Agents; Anti-Infective Agents, Local; Antifungal Agents

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2014)

    EXPL THER Thymol, a naturally occurring monocyclic phenolic compound derived from Thymus vulgaris (Lamiaceae), has been reported to exhibit anti-inflammatory property in vivo and vitro. However, the mechanism of thymol is not clear. The aim of the present study was to investigate the effects of thymol on allergic inflammation in OVA-induced mice asthma and explore its mechanism. The model of mouse asthma was established by the induction of OVA. Thymol was orally administered at a dose of 4, 8, and 16 mg/kg body weight 1hr before OVA challenge. At 24h after the last challenge, mice were sacrificed, and the data were collected by various experimental methods. The results revealed that pretreatment with thymol reduced the level of OVA-specific IgE, inhibited recruitment of inflammatory cells into airway, and decreased the levels of IL-4, IL-5, and IL-13 in BALF. Moreover, the pathologic changes of lung tissues were obviously ameliorated and goblet cell hyperplasia was effectively inhibited by the pretreatment of thymol. In addition, thymol reduced the development of airway hyperresponsiveness and blocked the activation of NF-kappaB pathway. All data suggested that thymol ameliorated airway inflammation in OVA-induced mouse asthma, possibly through inhibiting NF-kappaB activation. These findings indicated that thymol may be used as an alternative agent for treating allergic asthma.

    PMID:24785965 Zhou E et al; Fitoterapia. 2014 Jul;96:131-7. doi: 10.1016/j.fitote.2014.04.016

    EXPL THER Obesity has become a worldwide health problem. Most of the synthetic anti-obesity drugs have failed to manage the obesity due to either ineffectiveness or adverse effect. The research of prominent chemical constituents from herbal for the management of obesity has greatly increased. The main objective of the present study was intended to examine the effects of thymol in high-fat diet (HFD)-induced obesity in murine model. Male Wistar rats were fed HFD for 6 weeks to induce obesity. Thymol (14 mg/kg) administered orally twice a day to HFD-fed rats for 4 weeks. Alteration in body weight gain, visceral fat-pads weight and serum biochemical markers were assessed. At the end of study, rats fed with HFD exhibited significantly (p< 0.001) enhanced body weight gain, visceral pad weight, lipids, alanine aminotransferase (ALT), aspartate aminotransaminase (AST), lactate dehydrogenase (LDH), blood urea nitrogen (BUN), glucose, insulin and leptin levels compared with rats fed with normal diets. Thymol treatment showed significantly (p< 0.001) decreased body weight gain, visceral fat-pad weights, lipids, ALT, AST, LDH, BUN, glucose, insulin, and leptin levels in HFD-induced obese rats. Furthermore, thymol treatment showed significantly decreased serum lipid peroxidation and increased antioxidant levels in HFD-induced obese rats. Thymol prevents HFD-induced obesity in murine model through several mechanisms including attenuation of visceral fat accumulation, lipid lowering action, improvement of insulin and leptin sensitivity and enhanced antioxidant potential.

    PMID:24175857 Haque MR et al; Toxicol Mech Methods. 2014 Feb;24(2):116-23. doi: 10.3109/15376516.2013.861888. Epub 2013 Dec 5

    EXPL THER Mast cells play a critical role in inflammatory skin diseases through releasing proinflammatory mediators; however, few therapies directly target these cells. In 1878, the use of topical thymol, a now recognized potent agonist for transient receptor potential channels, was first described to treat eczema and psoriasis. /The objective was/ to determine the mechanisms through which thymol can alter skin inflammation. METHODS: /This study/ examined the effect of topical thymol on IgE-dependent responses using a mast cell-dependent passive cutaneous anaphylaxis (PCA) model, as well as in vitro-cultured mast cells. Thymol dose-dependently inhibited PCA when administered topically 24 hours before antigen challenge but provoked an ear-swelling response directly on application. This direct effect was associated with local mast cell degranulation and was absent in histamine-deficient mice. However, unlike with PCA responses, there was no late-phase swelling. In vitro thymol directly triggered calcium flux in mast cells through transient receptor potential channel activation, along with degranulation and cytokine transcription. However, no cytokine protein was produced. Instead, thymol induced a significant increase in apoptotic cell death that was seen both in vitro and in vivo. /The authors/ propose that the efficacy of thymol in reducing IgE-dependent responses is through promotion of activation-induced apoptotic cell death of mast cells and that this likely explains the clinical benefits observed in early clinical reports.

    PMID:24486068 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4040322 Wechsler JB et al; J Allergy Clin Immunol. 133 (6): 1735-43 (2014)

    For more Therapeutic Uses (Complete) data for THYMOL (8 total), please visit the HSDB record page.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antifungal Agents

    Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

    Anti-Infective Agents, Local

    Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

    5.2 Absorption, Distribution and Excretion

    Aromatic herbs as feed additives in animal production are encountering growing interest, but data on the fate of the aromatic compounds from the plant in the animal body are very scarce. In the present study, thyme (Thymus vulgaris) herb consisting of leaves and flowers without stems was used as an ingredient in the diet for broilers. The herb was fed for 35 days to five groups of broilers (0, 0.1, 0.2, 0.3, and 1% w/w in the diet). Animal performance and the concentrations of the main essential oil component from thyme, thymol, were measured in gut contents, plasma and liver and muscle tissues using solid phase microextraction and gas chromatography/mass spectrometry. There were no differences between the groups in feed intake, daily weight gain, feed conversion and slaughter weight. Thymol was detected in gut contents, plasma and liver and muscle tissues. Increased intestinal thymol concentrations were found in the group with 1% thyme compared with the other groups (P<0.05). In liver and muscle tissues the thymol levels were close to the limit of quantification. The data do not indicate a positive effect of thyme on animal performance. With high dietary levels of thyme herb, thymol concentrations increased in gut contents and plasma but were very low in edible tissues such as liver and flesh.

    PMID:24862829 Haselmeyer A et al; J Sci Food Agric. 2014 May 24. doi: 10.1002/jsfa.6758.

    Thymol is readily absorbed from the gastrointestinal tract following oral administration. It is essentially excreted in the urine within the first 24 hours after absorption.

    Toxikologische Bewertung. Heidelberg, Berufsgenossenschaft der chemischen Industrie 259 38 p (2000)

    5.3 Metabolism/Metabolites

    Only small amounts of the absorbed substance undergo urinary excretion as hydroxylated compounds. Thymol is predominantly excreted unchanged and in the form of its glucuronide and sulfate conjugates.

    Toxikologische Bewertung. Heidelberg, Berufsgenossenschaft der chemischen Industrie 259 38 p (2000)

    Substituted monophenols, thymol ... which occur in essential oils of plants, particularly thyme, are ... conjugated with glucuronic acid & sulfate.

    Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 147

    Thymol has known human metabolites that include Thymoquinol, p-Cymen-8-en-3-ol, p-Cymene-2,3-diol, thymol O-glucuronide, and thymol sulfate.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.4 Mechanism of Action

    The potent role of thymol, a natural compound, in modulation of macrophage activity was evaluated by determining all the sequential steps involved during phagocytosis. We found a significant increase in the proliferation of splenocytes in the presence of thymol and it proved to be a good mitogen. Uptake capacity of macrophages was enhanced due to increased membrane fluidity after treatment with thymol and it also increases lysosomal activity of macrophages. Data of superoxide anion generation revealed the involvement of thymol in the generation of respiratory burst as it potentiated this property of macrophages at a concentration of 150 uM. In the case of TNF-a, IL-1beta and PGE(2) a decreased level of secretion was observed 154 pg/mL, 736.1 pg/mL, and 151 pg/mL respectively when compared with lipopolysaccharide treated cells, where the level of these cytokines was significantly high. We also determined the anti-complementary activity of thymol which showed to be more effective than rosmarinic acid. Thus, the results obtained from the study suggest the potential role of thymol as a natural immunostimulatory drug which can be used in the treatment of various immunological disorders.

    PMID:24316253 Chauhan AK et al; Int Immunopharmacol. 2014 Feb;18(2):340-6. doi: 10.1016/j.intimp.2013.11.025. Epub 2013 Dec 5.

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    02-Jan-2021
    30-Sep-2024
    KGS
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