You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-11 20:47:28 UTC
Update Date2016-02-11 02:44:02 UTC
HMDB IDHMDB35770
Secondary Accession NumbersNone
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. 5-Isopropyl-2-methylphenol belongs to the family of Aromatic Monoterpenes. These are monoterpenes containing at least one aromatic ring.
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 Weight150.2176
Monoisotopic Molecular Weight150.10446507
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 KeyInChIKey=RECUKUPTGUEGMW-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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrient
Application
  • Flavoring Agent
  • Nutrient
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.27 m3·mol-1ChemAxon
Polarizability17.88 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-33df3527bcfd42c1888bView in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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
NuGOwiki LinkHMDB35770
Metagene LinkHMDB35770
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. [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. [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. [3531299 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.