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Record Information
Version4.0
Creation Date2012-09-11 20:47:28 UTC
Update Date2017-09-27 08:30:59 UTC
HMDB IDHMDB0035770
Secondary Accession Numbers
  • HMDB35770
Metabolite Identification
Common Name5-Isopropyl-2-methylphenol
Description5-Isopropyl-2-methylphenol is found in black walnut. 5-Isopropyl-2-methylphenol is a constituent of many essential oils. Especially found in the Labiatae. Thyme oil (=70%) and Origanum oil (=80%) are rich sources. 5-Isopropyl-2-methylphenol is a flavouring ingredient
Structure
Thumb
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
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
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
  • O-cresol
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

  Food and nutrition:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point3.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.25 mg/mL at 25 °CNot Available
LogP3.49Not Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-1900000000-ef32f1d484b3c21ba134View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0900000000-b0006c01682dd3cd5032View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-6900000000-b77d2bc899f0364b95e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8a9c632983ea0192ea86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-4025c9fcbf16ad5dc869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lec-9500000000-d3d61486758aa2c087bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-15cb932418fd2314ac11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d2de9111b421bbc52608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-3900000000-cae7a0406163986d258dView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-33df3527bcfd42c1888bView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID672
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014512
KNApSAcK IDC00000156
Chemspider ID21105867
KEGG Compound IDC09840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10364
PDB IDNot Available
ChEBI ID3440
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.. .