Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:11:19 UTC |
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Update date | 2020-09-17 15:30:27 UTC |
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Primary ID | FDB014512 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | 5-Isopropyl-2-methylphenol |
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Description | Carvacrol 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). |
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CAS Number | 499-75-2 |
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Structure | |
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Synonyms | Synonym | Source |
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1-Hydroxy-2-methyl-5-isopropylbenzene | ChEBI | 1-Methyl-2-hydroxy-4-isopropylbenzene | ChEBI | 2-Hydroxy-p-cymene | ChEBI | 2-Methyl-5-(1-methylethyl)phenol | ChEBI | 2-Methyl-5-isopropylphenol | ChEBI | 2-p-Cymenol | ChEBI | 3-Isopropyl-6-methylphenol | ChEBI | 5-Isopropyl-O-cresol | ChEBI | 2-Hydroxy-4-isopropyl-1-methylbenzene | HMDB | 2-Hydroxycymene | HMDB | 2-Methyl-5-(1-methylethyl)-phenol | HMDB | 3-Isopropyl-6-methyl-phenol | HMDB | 5-Isopropyl-2-methyl-phenol | HMDB | 6-Methyl-3-isopropylphenol | HMDB | Antioxine | HMDB | BENZENE,2-hydroxy,4-isopropyl,1-methyl carvacrol | HMDB | Carvacrol | HMDB | Cymenol | HMDB | Cymophenol | HMDB | FEMA 2245 | HMDB | Hydroxy-P-cymene | HMDB | Isopropyl-O-cresol | HMDB | Isothymol | HMDB | Isothymol (=2-isopropyl-4-methyl phenol) | HMDB | Karvakrol | HMDB | Methyl-5-(1-methylethyl)phenol | HMDB | O-Thymol | HMDB | Oxycymol | HMDB | P-Cymen-2-ol | HMDB | P-Cymene-2-ol | HMDB | P-Mentha-1,3,5-trien-2-ol | HMDB | 5-Isopropyl-2-methylphenol | ChEBI | 5-Isopropyl-o-cresol | db_source | 6-methyl-3-isopropylphenol | biospider | BENZENE,2-HYDROXY,4-ISOPROPYL,1-METHYL CARVACROL | biospider | Cymene-2-ol, p- | biospider | Hydroxy-p-cymene | biospider | Isopropyl-o-cresol | biospider | Isothymol (=2-Isopropyl-4-methyl phenol) | biospider | o-Cresol, 5-isopropyl- | biospider | O-thymol | biospider | p-Cymen-2-ol | db_source | p-Cymene, 2-hydroxy- | biospider | p-Mentha-1,3,5-trien-2-ol | db_source | Phenol, 2-methyl-5-(1-methylethyl)- | biospider | Phenol, 3-isopropyl-6-methyl- | biospider | Phenol, 5-isopropyl-2-methyl- | biospider |
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Predicted Properties | |
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Chemical Formula | C10H14O |
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IUPAC name | 2-methyl-5-(propan-2-yl)phenol |
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InChI Identifier | InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 |
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InChI Key | RECUKUPTGUEGMW-UHFFFAOYSA-N |
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Isomeric SMILES | CC(C)C1=CC(O)=C(C)C=C1 |
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Average Molecular Weight | 150.221 |
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Monoisotopic Molecular Weight | 150.104465071 |
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Classification |
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Description | Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Monoterpenoids |
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Direct Parent | Aromatic monoterpenoids |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: Biological role: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Liquid | |
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Physical Description | Not Available | |
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Mass Composition | C 79.96%; H 9.39%; O 10.65% | DFC |
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Melting Point | Mp 3.5° | DFC |
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Boiling Point | Bp10 113° | DFC |
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Experimental Water Solubility | 1.25 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Experimental logP | 3.49 | GRIFFIN,S ET AL. (1999) |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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EI-MS | Mass Spectrum (Electron Ionization) | splash10-000i-3900000000-33df3527bcfd42c1888b | 2015-03-01 | View Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-1900000000-ef32f1d484b3c21ba134 | Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-0900000000-b0006c01682dd3cd5032 | Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-6900000000-b77d2bc899f0364b95e6 | Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-1900000000-ef32f1d484b3c21ba134 | Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-0900000000-b0006c01682dd3cd5032 | Spectrum | GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, GC-MS Spectrum | splash10-000i-6900000000-b77d2bc899f0364b95e6 | Spectrum | Predicted GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0k9i-3900000000-3be7e2bf4cdcc1a3e998 | Spectrum | Predicted GC-MS | 5-Isopropyl-2-methylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ab9-9770000000-bfcdd12ac3af31af5d4d | Spectrum | Predicted GC-MS | 5-Isopropyl-2-methylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - QTOF 3V, positive | splash10-0udi-0900000000-712524634787b6273922 | 2020-07-22 | View Spectrum | MS/MS | LC-MS/MS Spectrum - n/a 10V, positive | splash10-0a4i-0900000000-68880fe4b40d01db1716 | 2020-07-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900000000-8a9c632983ea0192ea86 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-2900000000-4025c9fcbf16ad5dc869 | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0lec-9500000000-d3d61486758aa2c087bd | 2016-06-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-15cb932418fd2314ac11 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-d2de9111b421bbc52608 | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00ls-3900000000-cae7a0406163986d258d | 2016-08-03 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0002-0900000000-22917433edc8ad9dbc2e | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-0900000000-ec9ac6baa6857dfd0b60 | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05o3-7900000000-102f2168cf41515b9d4d | 2021-09-23 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0k96-6900000000-a06e5e505d76cfe47ff1 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9400000000-97275967d77e94a70074 | 2021-09-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-004l-9100000000-623acc544c8c7c8ef29a | 2021-09-24 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum |
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External Links |
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ChemSpider ID | 21105867 |
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ChEMBL ID | CHEMBL281202 |
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KEGG Compound ID | C09840 |
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Pubchem Compound ID | 10364 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | 672 |
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DrugBank ID | Not Available |
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HMDB ID | HMDB35770 |
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CRC / DFC (Dictionary of Food Compounds) ID | JRM60-H:JRM60-H |
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EAFUS ID | 545 |
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Dr. Duke ID | ISOTHYMOL|CARVACROL |
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BIGG ID | Not Available |
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KNApSAcK ID | C00000156 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | rw1027311 |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
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allergenic | 50904 | A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. | DUKE | anesthetic | | | DUKE | anti helmintic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti Alzheimeran | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti atherosclerotic | 38070 | 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 bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti cholinesterase | 37733 | An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). | DUKE | anti diuretic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti melanomic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | antioxidant | 22586 | 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 plaque | | | DUKE | anti prostaglandin | 49020 | 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 radicular | | | DUKE | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti streptococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti tussive | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | candidicide | | | DUKE | carminative | | | DUKE | cyclooxygenase inhibitor | 35544 | 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 | enterorelaxant | | | DUKE | expectorant | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | insectifuge | 24852 | 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 | irritant | | | DUKE | nematicide | 25491 | A substance used to destroy pests of the phylum Nematoda (roundworms). | DUKE | pesticide | 25944 | 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 inhibitor | 49023 | A compound that inhibits the action of prostaglandins. | DUKE | tracheorelaxant | | | DUKE | trichomonicide | | | DUKE | vermifuge | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Flavor | Citations |
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spice |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| woody |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| camphor |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| thymol |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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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.
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