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
Synonyms
SynonymSource
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
5-Isopropyl-o-cresoldb_source
6-methyl-3-isopropylphenolbiospider
BENZENE,2-HYDROXY,4-ISOPROPYL,1-METHYL CARVACROLbiospider
Cymene-2-ol, p-biospider
Hydroxy-p-cymenebiospider
Isopropyl-o-cresolbiospider
Isothymol (=2-Isopropyl-4-methyl phenol)biospider
o-Cresol, 5-isopropyl-biospider
O-thymolbiospider
p-Cymen-2-oldb_source
p-Cymene, 2-hydroxy-biospider
p-Mentha-1,3,5-trien-2-oldb_source
Phenol, 2-methyl-5-(1-methylethyl)-biospider
Phenol, 3-isopropyl-6-methyl-biospider
Phenol, 5-isopropyl-2-methyl-biospider
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
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 substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.DUKE
AnestheticA drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.DUKE
Anti-helmintic33281 An agent that kills or expels parasitic worms, treating helminthic infections. Therapeutically, it targets intestinal parasites, reducing infection symptoms. Key medical uses include treating roundworm, hookworm, and tapeworm infections.DUKE
Anti-Alzheimeran52217 An agent that inhibits the progression of Alzheimer's disease, reducing beta-amyloid plaque formation and neuroinflammation. Therapeutically, it improves cognitive function and memory, commonly used in managing mild to moderate Alzheimer's disease and other neurodegenerative disorders.DUKE
Anti-atherosclerotic38070 An agent that prevents or slows the formation of atherosclerosis, a condition characterized by plaque buildup in arteries. It reduces inflammation, improves lipid profiles, and inhibits platelet aggregation, commonly used to manage cardiovascular diseases, such as coronary artery disease, and prevent heart attacks and strokes.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti cholinesterase37733 An agent that inhibits acetylcholinesterase, increasing acetylcholine levels, and enhancing cholinergic transmission. Therapeutically, it's used to treat myasthenia gravis, glaucoma, and Alzheimer's disease, improving muscle strength, reducing eye pressure, and enhancing cognitive function.DUKE
Anti diuretic52217 An agent that reduces urine production, regulating water balance in the body. It plays a biological role in conserving water and electrolytes. Therapeutically, it is used to treat conditions like diabetes insipidus, nocturnal enuresis, and SIADH, helping to manage fluid balance and prevent dehydration.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-melanomic35610 An agent that inhibits melanin production, reducing melanoma cell growth. It has therapeutic applications in treating skin cancers, particularly melanoma, and key medical uses include preventing tumor progression and metastasis, as well as managing pigmentation disorders.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti-plaqueAn agent that removes or prevents the formation of dental plaque, a biofilm of bacteria, to prevent tooth decay and gum disease, commonly used in oral care products and therapeutic applications for periodontal health.DUKE
Anti prostaglandin49020 An agent that inhibits prostaglandin production, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and post-surgical pain, by blocking prostaglandin-mediated responses, providing relief from inflammation and discomfort.DUKE
Anti radicularAn agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-staphylococcic33282 An agent that combats Staphylococcus infections, playing a crucial role in preventing bacterial growth. Therapeutically, it is used to treat skin and soft tissue infections, respiratory tract infections, and bloodstream infections. Key medical uses include treating methicillin-resistant Staphylococcus aureus (MRSA) and other staphylococcal infections, reducing the risk of infection and promoting wound healing.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
Anti-tussive52217 An agent that suppresses coughing, reducing the frequency and severity of coughs. It works by targeting the brain's cough center, providing therapeutic relief for dry, irritating coughs. Key medical uses include managing coughs associated with colds, flu, and other respiratory conditions.DUKE
CandidicideAn agent that kills Candida species, such as Candida albicans, reducing fungal infections. Therapeutically, it is used to treat candidiasis, with key medical applications in managing oral thrush, vaginal yeast infections, and other fungal diseases.DUKE
CarminativeAn agent that prevents or relieves gas in the gastrointestinal tract, facilitating its expulsion and combating flatulence, commonly used to soothe digestive issues and alleviate symptoms of bloating and discomfort.DUKE
Cyclooxygenase inhibitor35544 An agent that blocks the activity of cyclooxygenase enzymes, reducing inflammation and pain. Therapeutically, it is used to treat conditions such as arthritis, headaches, and menstrual cramps, by decreasing prostaglandin production, a key mediator of inflammation.DUKE
EnterorelaxantAn agent that reduces or inhibits the movement of intestinal muscles, relieving spasms and cramps. Therapeutically, it's used to treat irritable bowel syndrome, diarrhea, and other gastrointestinal disorders, providing relief from abdominal pain and discomfort.DUKE
Expectorant52217 An agent that thins and loosens mucus, making it easier to cough up, reducing congestion. It aids in clearing respiratory tract secretions, commonly used to relieve coughs, colds, and bronchitis, promoting easier breathing and soothing irritated airways.DUKE
Name48318 flavorDUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Insectifuge24852 A substance that repels insects, playing a biological role in plant defense. Therapeutically, it has applications in preventing insect-borne diseases. Key medical uses include topical repellents for malaria, dengue fever, and other vector-borne illnesses, reducing the risk of transmission.DUKE
IrritantAn agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.DUKE
Nematicide25491 An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Prostaglandin inhibitor49023 An agent that blocks the production or action of prostaglandins, reducing inflammation and pain. Therapeutically, it's used to treat conditions like arthritis, menstrual cramps, and fever, by decreasing prostaglandin-mediated responses, providing relief from symptoms.DUKE
TracheorelaxantAn agent that relaxes tracheal smooth muscle, easing breathing by reducing airway resistance, commonly used to treat respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD).DUKE
TrichomonicideAn agent that kills Trichomonas organisms, used to treat Trichomonas vaginalis infections, commonly causing vaginitis, and other related genital tract infections.DUKE
Vermifuge25944 An agent that expels or destroys intestinal parasites, such as worms, by paralyzing or killing them, commonly used to treat parasitic infections like hookworm, roundworm, and tapeworm infestations.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.