Showing Compound Card for Thymol (CDB000672)

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Record Information
Version1.0
Created at2020-03-19 00:50:22 UTC
Updated at2020-12-07 19:07:39 UTC
CannabisDB IDCDB000672
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameThymol
DescriptionThymol, also known as 3-p-cymenol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. In a 1994 report released by five top cigarette companies, thymol is one of the 599 additives to cigarettes. Thymol is a very hydrophobic molecule, practically insoluble in water, but fairly soluble in organic solvents. Thus, thymol is considered to be an isoprenoid lipid molecule. Thymol is found in the essential oil of thyme and in the essential oils of several different plants. It can be extracted from Thymus vulgaris (common thyme), Ajwain and various other kinds of plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. vulgaris. Thymol has also been identified as a volatile compound found in cannabis samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-5-methyl-2-isopropylbenzeneChEBI
2-Isopropyl-5-methylphenolChEBI
3-p-CymenolChEBI
5-METHYL-2-(1-methylethyl)phenolChEBI
5-Methyl-2-isopropylphenolChEBI
6-Isopropyl-3-methylphenolChEBI
6-Isopropyl-m-cresolChEBI
1-Methyl-3-hydroxy-4-isopropylbenzeneHMDB
2-Hydroxy-1-isopropyl-4-methylbenzeneHMDB
3-Hydroxy-1-methyl-4-isopropylbenzeneHMDB
3-Hydroxy-P-cymeneHMDB
3-Methyl-6-isopropylphenolHMDB
5-Methyl-2-isopropyl-1-phenolHMDB
6-Isopropyl-P-cresolHMDB
Isopropyl cresolHMDB
Isopropyl-m-cresolHMDB
m-ThymolHMDB
P-Cymen-3-olHMDB
ThymateHMDB
Thyme camphorHMDB
Thymic acidHMDB
Thymol crystal purissHMDB
Thymol swarm brandMeSH, HMDB
ApiguardMeSH, HMDB
Swarm brand OF thymolMeSH, HMDB
Chemical FormulaC10H14O
Average Molecular Weight150.22
Monoisotopic Molecular Weight150.1045
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 KeyMGSRCZKZVOBKFT-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Cumene
  • Phenylpropane
  • M-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Toluene
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point51.5 °CNot Available
Boiling Point232 °CWikipedia
Water Solubility0.9 mg/mL at 20 °CNot Available
logP3.30HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-4900000000-73edaa628c1f5f2e1bd92015-03-01View Spectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-333dc57384e65e3b4cfaSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-1900000000-3679938a5ea114a30e48Spectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-3900000000-8ce5865e48dad7250d5eSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-0udi-0109030000-5562c203cb318f30321bSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-0a4i-2492200000-85342d698be72263a95fSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-333dc57384e65e3b4cfaSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-1900000000-3679938a5ea114a30e48Spectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-000i-3900000000-8ce5865e48dad7250d5eSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-0udi-0109030000-5562c203cb318f30321bSpectrum
GC-MSThymol, non-derivatized, GC-MS Spectrumsplash10-0a4i-2492200000-85342d698be72263a95fSpectrum
Predicted GC-MSThymol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-3900000000-e309fdc1ab0cd926b420Spectrum
Predicted GC-MSThymol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9880000000-3a69bebdbca0f95e862aSpectrum
Predicted GC-MSThymol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSThymol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-01p9-9700000000-e1a28495617d7b014e5c2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9300000000-baeee6cdcafaadeebdec2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-015c-9100000000-e1efa41eaf818832448a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (SHIMADZU LKB-9000B) , Positivesplash10-000i-0900000000-333dc57384e65e3b4cfa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6L) , Positivesplash10-000i-1900000000-3679938a5ea114a30e482012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-000i-3900000000-f72f603d97f0f7081b8d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 10V, negativesplash10-0002-0900000000-d3ae016121d86e17ddb42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 13V, negativesplash10-0002-1900000000-3e340243a54a9e3f0da42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-QFT 19V, negativesplash10-00dm-8900000000-82e846f2a3546e27414c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, negativesplash10-0002-0900000000-844f0c545c66f6c639932020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-0a4i-0900000000-d30a5d305446b3540d852020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-4e6c9c70215576f53b602021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-2900000000-eeb06bc7587fcef0ba862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-a8236f8b0194b3d088442021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-be4566e335ee9b00c7242021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-fde7d3d2a42203ba2b952021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-92d1da1fba9df31389ed2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-32e3f430e6dfc819272b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-19305d290c7303afc3f52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pw9-7900000000-b0fcecf9ea71d35284082016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1b21dedfdc78e416ea8f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-43b3e1a99ba193849bf42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0532-3900000000-a152936b0bcf0d3200922016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-9800000000-947167dd66d5b69474162021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9600000000-df6822dada158a51482c2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001878
DrugBank IDDB02513
Phenol Explorer Compound ID671
FoodDB IDFDB014795
KNApSAcK IDC00000155
Chemspider ID21105998
KEGG Compound IDC09908
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThymol
METLIN ID4245
PubChem Compound6989
PDB IDNot Available
ChEBI ID27607
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]