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Record Information
Version3.6
Creation Date2006-02-24 11:46:47 UTC
Update Date2016-02-11 01:05:03 UTC
HMDB IDHMDB01878
Secondary Accession NumbersNone
Metabolite Identification
Common NameThymol
DescriptionThymol is a phenol obtained from thyme oil or other volatile oils. It is used as a stabilizer in pharmaceutic preparations. It has been used for its antiseptic, antibacterial, and antifungal actions, and was formerly used as a vermifuge. (Dorland, 28th ed) -- Pubchem; Thymol is a monoterpene phenol derivative of cymene, C10H13OH, isomeric with carvacrol, found in oil of thyme, and extracted as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. It is also called "hydroxy cymene". (from Webster's 1913 dictionary) -- Wikipedia; In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Its use or purpose, however, is unknown, like most cigarette additives. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
1-Hydroxy-5-methyl-2-isopropylbenzeneHMDB
1-Methyl-3-hydroxy-4-isopropylbenzeneHMDB
2-Hydroxy-1-isopropyl-4-methylbenzeneHMDB
2-Isopropyl-5-methylphenolHMDB
3-Hydroxy-1-methyl-4-isopropylbenzeneHMDB
3-Hydroxy-P-cymeneHMDB
3-Methyl-6-isopropylphenolHMDB
3-P-CymenolHMDB
5-Methyl-2-(1-methylethyl)phenolHMDB
5-Methyl-2-isopropyl-1-phenolHMDB
5-Methyl-2-isopropylphenolHMDB
6-Isopropyl-3-methylphenolHMDB
6-Isopropyl-m-cresolHMDB
6-Isopropyl-P-cresolHMDB
Isopropyl cresolHMDB
Isopropyl-m-cresolHMDB
m-ThymolHMDB
P-Cymen-3-olHMDB
ThymateHMDB
Thyme camphorHMDB
Thymic acidHMDB
Thymol crystal purissHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name5-methyl-2-(propan-2-yl)phenol
Traditional Namethymol
CAS Registry Number89-83-8
SMILES
CC(C)C1=C(O)C=C(C)C=C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3
InChI KeyInChIKey=MGSRCZKZVOBKFT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • M-cresol
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point51.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.9 mg/mL at 20 °CNot Available
LogP3.30HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.64 mg/mLALOGPS
logP3.16ALOGPS
logP3.43ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.59ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m3·mol-1ChemAxon
Polarizability17.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01p9-9700000000-e1a28495617d7b014e5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-baeee6cdcafaadeebdecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-9100000000-e1efa41eaf818832448aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-000i-0900000000-333dc57384e65e3b4cfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-000i-1900000000-3679938a5ea114a30e48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-000i-3900000000-f72f603d97f0f7081b8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000i-4900000000-73edaa628c1f5f2e1bd9View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Saliva
  • Urine
Tissue Location
  • Liver
  • Skeletal Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified3.264 +/- 1.01 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified2.2 (0.7-4.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified6.623 +/- 5.826 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02513
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID671
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014795
KNApSAcK IDC00000155
Chemspider ID21105998
KEGG Compound IDC09908
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThymol
NuGOwiki LinkHMDB01878
Metagene LinkHMDB01878
METLIN ID4245
PubChem Compound6989
PDB IDIPB
ChEBI ID27607
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kohlert C, Schindler G, Marz RW, Abel G, Brinkhaus B, Derendorf H, Grafe EU, Veit M: Systemic availability and pharmacokinetics of thymol in humans. J Clin Pharmacol. 2002 Jul;42(7):731-7. [12092740 ]
  2. Kharchenko NK: [Dopamine content in blood and activity of alcohol-transforming enzymes in alcoholism] Ukr Biokhim Zh. 1997 Mar-Apr;69(2):87-92. [9463245 ]
  3. Haeseler G, Maue D, Grosskreutz J, Bufler J, Nentwig B, Piepenbrock S, Dengler R, Leuwer M: Voltage-dependent block of neuronal and skeletal muscle sodium channels by thymol and menthol. Eur J Anaesthesiol. 2002 Aug;19(8):571-9. [12200946 ]
  4. Attin R, Tuna A, Attin T, Brunner E, Noack MJ: Efficacy of differently concentrated chlorhexidine varnishes in decreasing Mutans streptococci and lactobacilli counts. Arch Oral Biol. 2003 Jul;48(7):503-9. [12798153 ]
  5. Sotto A, Alvarez JL, Garcia B, Pomar F, Cendan A: [Acute hepatic lesion caused by Giardia lamblia] Rev Esp Enferm Dig. 1990 Jan;77(1):24-8. [2334580 ]
  6. Chen Y, Pietrzyk RA, Whitson PA: Quantification of urinary uric acid in the presence of thymol and thimerosal by high-performance liquid chromatography. J Chromatogr A. 1997 Feb 28;763(1-2):187-92. [9129322 ]
  7. Kohlert C, Abel G, Schmid E, Veit M: Determination of thymol in human plasma by automated headspace solid-phase microextraction-gas chromatographic analysis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Feb 5;767(1):11-8. [11863281 ]
  8. Kern M, Fechtig T, Strub JR: Influence of water storage and thermal cycling on the fracture strength of all-porcelain, resin-bonded fixed partial dentures. J Prosthet Dent. 1994 Mar;71(3):251-6. [8164166 ]
  9. Hazout S, Lockhart AM, Taillefer MH, Philippon C, Valleron AJ, Dhumeaux D: The thymol turbidity test and determination of serum cholesterol : two tests to abandon in the routine evaluation of liver function. Biomedicine. 1978 Oct;28(5):288-92. [743555 ]
  10. Gentile S, Bajema BL, Baldini G, Lunazzi G, Groothuis GM, Tiribelli C, Meijer DK, Sottocasa GL: Measurement of the association of cholephylic organic anions with different binding proteins. Biochem Pharmacol. 1985 Jul 15;34(14):2439-44. [4015687 ]