Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for Thymol (HMDB01878)

Record Information
Version 3.5
Creation Date 2006-02-24 04:46:47 -0700
Update Date 2013-04-08 13:34:52 -0600
HMDB ID HMDB01878
Secondary Accession Numbers None
Metabolite Identification
Common Name Thymol
Description Thymol 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Hydroxy-5-methyl-2-isopropylbenzene
  2. 1-Methyl-3-hydroxy-4-isopropylbenzene
  3. 2-Hydroxy-1-isopropyl-4-methylbenzene
  4. 2-Isopropyl-5-methylphenol
  5. 3-Hydroxy-1-methyl-4-isopropylbenzene
  6. 3-Hydroxy-p-cymene
  7. 3-Methyl-6-isopropylphenol
  8. 3-p-Cymenol
  9. 5-Methyl-2-(1-methylethyl)phenol
  10. 5-Methyl-2-isopropyl-1-phenol
  11. 5-Methyl-2-isopropylphenol
  12. 6-Isopropyl-3-methylphenol
  13. 6-Isopropyl-m-cresol
  14. 6-Isopropyl-p-cresol
  15. Isopropyl cresol
  16. Isopropyl-m-cresol
  17. m-Thymol
  18. p-Cymen-3-ol
  19. Thymate
  20. Thyme camphor
  21. Thymic acid
  22. Thymol
  23. Thymol crystal puriss
Chemical Formula C10H14O
Average Molecular Weight 150.2176
Monoisotopic Molecular Weight 150.10446507
IUPAC Name 5-methyl-2-(propan-2-yl)phenol
Traditional IUPAC Name thymol
CAS Registry Number 89-83-8
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 Key MGSRCZKZVOBKFT-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Monoterpenes
Other Descriptors
  • C10 isoprenoids (monoterpenes)(Lipidmaps)
  • Cumenes
  • Cyclic monoterpenes(KEGG)
  • Menthane monoterpenoids(KEGG)
  • Monocyclic Monoterpenes
  • Organic Compounds
  • phenols(ChEBI)
Substituents
  • M Cresol
  • Phenol
  • Phenol Derivative
  • Toluene
Direct Parent Aromatic Monoterpenes
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 51.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.9 mg/mL at 20 °C Not Available
LogP 3.30 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.64 g/L ALOGPS
LogP 3.16 ALOGPS
LogP 3.43 ChemAxon
LogS -2.37 ALOGPS
pKa (strongest acidic) 10.59 ChemAxon
pKa (strongest basic) -5.2 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 47.27 ChemAxon
Polarizability 17.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (SHIMADZU LKB-9000B)
MS/MS Spectrum EI-B (HITACHI RMU-6L)
MS/MS Spectrum EI-B (HITACHI M-80B)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Skeletal Muscle
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
2.2 (0.7-4.0) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB02513 Link_out
Phenol Explorer Compound ID 671 Link_out
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB014795
KNApSAcK ID C00000155 Link_out
Chemspider ID 21105998 Link_out
KEGG Compound ID C09908 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Thymol Link_out
NuGOwiki Link HMDB01878 Link_out
Metagene Link HMDB01878 Link_out
METLIN ID 4245 Link_out
PubChem Compound 6989 Link_out
PDB ID IPB Link_out
ChEBI ID 27607 Link_out
References
Synthesis Reference Not 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. Pubmed: 12092740 Link_out
  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. Pubmed: 9463245 Link_out
  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. Pubmed: 12200946 Link_out
  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. Pubmed: 12798153 Link_out
  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. Pubmed: 2334580 Link_out
  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. Pubmed: 9129322 Link_out
  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. Pubmed: 11863281 Link_out
  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. Pubmed: 8164166 Link_out
  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. Pubmed: 743555 Link_out
  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. Pubmed: 4015687 Link_out