| Record Information |
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| Version | 2.0 |
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| Created at | 2012-09-11 20:47:28 UTC |
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| Updated at | 2024-09-03 04:22:25 UTC |
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| NP-MRD ID | NP0001326 |
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| Natural Product DOI | https://doi.org/10.57994/2851 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 5-Isopropyl-2-methylphenol |
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| Description | 5-Isopropyl-2-methylphenol, also known as 2-hydroxy-p-cymene or 2-p-cymenol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. 5-Isopropyl-2-methylphenol is a very hydrophobic molecule, practically insoluble in water, but fairly soluble in organic solvents. Thus, 5-Isopropyl-2-methylphenol is considered to be an isoprenoid lipid molecule. Thymol is found in the essential oil of thyme and in the essential oils of several different plants. It can be extracted from Thymus vulgaris (common thyme), Ajwain and various other kinds of plants as a white crystalline substance of a pleasant aromatic odor and strong antiseptic properties. Thymol also provides the distinctive, strong flavor of the culinary herb thyme, also produced from T. Vulgaris. Thymol has also been identified as a volatile compound found in cannabis samples obtained from police seizures (PMID:26657499 ). |
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| Structure | InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 |
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| Synonyms | | Value | 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 |
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| Chemical Formula | C10H14O |
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| Average Mass | 150.2210 Da |
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| Monoisotopic Mass | 150.10447 Da |
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| IUPAC Name | 2-methyl-5-(propan-2-yl)phenol |
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| Traditional Name | carvacrol |
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| CAS Registry Number | 499-75-2 |
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| SMILES | CC(C)C1=CC(O)=C(C)C=C1 |
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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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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 800, CD3OD, simulated) | ztmnb@umsystem.edu | Sumner lab, University of Missouri | Zach Tretter | 2024-06-18 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Liquid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 3.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1.25 mg/mL at 25 °C | Not Available | | LogP | 3.49 | Not Available |
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| Predicted Properties | |
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| General References | - 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 ]
- 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 ]
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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