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5-Isopropyl-2-methylphenol (FDB014512)

Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2020-09-17 15:30:27 UTC
Primary IDFDB014512
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-Isopropyl-2-methylphenol
DescriptionCarvacrol or 5-isopropyl-2-methylphenol is a naturally occurring organic compound classified as an alkylphenol (containing at least one aromatic ring) although biochemically, it is a monoterpenoid synthesized from isoprene units. Carvacrol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Carvacrol has a camphor, spice, and thymol taste with a characteristic pungent, warm odor of oregano. Carvacrol is found in highest concentrations in pot marjorams, common thymes, and black walnuts and in lower concentrations in rosemaries, common oregano, and sweet marjorams. Carvacrol was detected in pepper (spice), tamarinds, peppermints, lovages, and sweet basils making carvacrol a potential biomarker for the consumption of these foods. It has been added as a flavoring agent, preservative and fragrance in products. Its bioactivity and toxicological properties have been reviewed (PMID: 24915411). As a constituent of many essential oils, carvocrol was demonstrated to have anti-biofilm and anti-microbial properties (PMID: 30067078) and acts as an anti-viral against the norovirus (PMID: 24779581).
CAS Number499-75-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H14O
IUPAC name2-methyl-5-(propan-2-yl)phenol
InChI IdentifierInChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3
InChI KeyRECUKUPTGUEGMW-UHFFFAOYSA-N
Isomeric SMILESCC(C)C1=CC(O)=C(C)C=C1
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
Classification
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:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 79.96%; H 9.39%; O 10.65%DFC
Melting PointMp 3.5°DFC
Boiling PointBp10 113°DFC
Experimental Water Solubility1.25 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP3.49GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-33df3527bcfd42c1888b2015-03-01View Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-1900000000-ef32f1d484b3c21ba134Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-b0006c01682dd3cd5032Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-6900000000-b77d2bc899f0364b95e6Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-1900000000-ef32f1d484b3c21ba134Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-0900000000-b0006c01682dd3cd5032Spectrum
GC-MS5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrumsplash10-000i-6900000000-b77d2bc899f0364b95e6Spectrum
Predicted GC-MS5-Isopropyl-2-methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0k9i-3900000000-3be7e2bf4cdcc1a3e998Spectrum
Predicted GC-MS5-Isopropyl-2-methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9770000000-bfcdd12ac3af31af5d4dSpectrum
Predicted GC-MS5-Isopropyl-2-methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - QTOF 3V, positivesplash10-0udi-0900000000-712524634787b62739222020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0a4i-0900000000-68880fe4b40d01db17162020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-8a9c632983ea0192ea862016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-2900000000-4025c9fcbf16ad5dc8692016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lec-9500000000-d3d61486758aa2c087bd2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-15cb932418fd2314ac112016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-d2de9111b421bbc526082016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ls-3900000000-cae7a0406163986d258d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-ec9ac6baa6857dfd0b602021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05o3-7900000000-102f2168cf41515b9d4d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0k96-6900000000-a06e5e505d76cfe47ff12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9400000000-97275967d77e94a700742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9100000000-623acc544c8c7c8ef29a2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
ChemSpider ID21105867
ChEMBL IDCHEMBL281202
KEGG Compound IDC09840
Pubchem Compound ID10364
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID672
DrugBank IDNot Available
HMDB IDHMDB35770
CRC / DFC (Dictionary of Food Compounds) IDJRM60-H:JRM60-H
EAFUS ID545
Dr. Duke IDISOTHYMOL|CARVACROL
BIGG IDNot Available
KNApSAcK IDC00000156
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1027311
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anti helmintic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti atherosclerotic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti cholinesterase37733 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).DUKE
anti diuretic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti melanomic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti plaqueDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti radicularDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
candidicideDUKE
carminativeDUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
enterorelaxantDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
irritantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin inhibitor49023 A compound that inhibits the action of prostaglandins.DUKE
tracheorelaxantDUKE
trichomonicideDUKE
vermifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spice
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
thymol
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.