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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 20:47:28 UTC
Update Date2021-09-07 17:05:35 UTC
HMDB IDHMDB0035770
Secondary Accession Numbers
  • HMDB35770
Metabolite Identification
Common Name5-Isopropyl-2-methylphenol
Description5-Isopropyl-2-methylphenol, also known as 2-hydroxy-p-cymene or 2-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-erythritol-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. 5-Isopropyl-2-methylphenol is a very hydrophobic molecule, practically insoluble in water, but fairly soluble in organic solvents. Thus, 5-Isopropyl-2-methylphenol 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
Data?1563862769
Synonyms
ValueSource
1-Hydroxy-2-methyl-5-isopropylbenzeneChEBI
1-Methyl-2-hydroxy-4-isopropylbenzeneChEBI
2-Hydroxy-p-cymeneChEBI
2-Methyl-5-(1-methylethyl)phenolChEBI
2-Methyl-5-isopropylphenolChEBI
2-p-CymenolChEBI
3-Isopropyl-6-methylphenolChEBI
5-Isopropyl-O-cresolChEBI
2-Hydroxy-4-isopropyl-1-methylbenzeneHMDB
2-HydroxycymeneHMDB
2-Methyl-5-(1-methylethyl)-phenolHMDB
3-Isopropyl-6-methyl-phenolHMDB
5-Isopropyl-2-methyl-phenolHMDB
6-Methyl-3-isopropylphenolHMDB
AntioxineHMDB
BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrolHMDB
CarvacrolHMDB
CymenolHMDB
CymophenolHMDB
FEMA 2245HMDB
Hydroxy-p-cymeneHMDB
Isopropyl-O-cresolHMDB
IsothymolHMDB
Isothymol (=2-isopropyl-4-methyl phenol)HMDB
KarvakrolHMDB
Methyl-5-(1-methylethyl)phenolHMDB
O-ThymolHMDB
OxycymolHMDB
p-Cymen-2-olHMDB
p-Cymene-2-olHMDB
p-Mentha-1,3,5-trien-2-olHMDB
5-Isopropyl-2-methylphenolChEBI
Chemical FormulaC10H14O
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
IUPAC Name2-methyl-5-(propan-2-yl)phenol
Traditional Namecarvacrol
CAS Registry Number499-75-2
SMILES
CC(C)C1=CC(O)=C(C)C=C1
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
InChI KeyRECUKUPTGUEGMW-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
  • O-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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point3.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.25 mg/mL at 25 °CNot Available
LogP3.49Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP3.2ALOGPS
logP3.43ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)10.42ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m³·mol⁻¹ChemAxon
Polarizability17.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available133.6231661259
DarkChem[M-H]-PredictedNot Available131.18731661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
5-Isopropyl-2-methylphenol,1TMS,#11324.5374https://arxiv.org/abs/1905.12712
5-Isopropyl-2-methylphenol,1TBDMS,#11563.8914https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-1900000000-ef32f1d484b3c21ba1342017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-b0006c01682dd3cd50322017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-6900000000-b77d2bc899f0364b95e62017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-1900000000-ef32f1d484b3c21ba1342018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-b0006c01682dd3cd50322018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-6900000000-b77d2bc899f0364b95e62018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9i-3900000000-3be7e2bf4cdcc1a3e9982016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-9770000000-bfcdd12ac3af31af5d4d2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-33df3527bcfd42c1888b2015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0udi-0900000000-712524634787b62739222020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-0900000000-68880fe4b40d01db17162020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8a9c632983ea0192ea862016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-4025c9fcbf16ad5dc8692016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lec-9500000000-d3d61486758aa2c087bd2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-15cb932418fd2314ac112016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d2de9111b421bbc526082016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-3900000000-cae7a0406163986d258d2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)2015-03-12View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID672
FooDB IDFDB014512
KNApSAcK IDC00000156
Chemspider ID21105867
KEGG Compound IDC09840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarvacrol
METLIN IDNot Available
PubChem Compound10364
PDB IDNot Available
ChEBI ID3440
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Alali F, Al-Lafi T: GC-MS analysis and bioactivity testing of the volatile oil from the leaves of the toothbrush tree Salvadora persica L. Nat Prod Res. 2003 Jun;17(3):189-94. [PubMed:12737403 ]
  2. Bekhechi C, Boti JB, Bekkara FA, Abdelouahid DE, Casanova J, Tomi F: Isothymol in Ajowan essential oil. Nat Prod Commun. 2010 Jul;5(7):1107-10. [PubMed:20734951 ]
  3. Rashid KA, Mumma RO: Screening pesticides for their ability to damage bacterial DNA. J Environ Sci Health B. 1986 Aug;21(4):319-34. [PubMed:3531299 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.