2,5-Dimethoxy-p-cymene
2,5-Dimethoxy-p-cymene, or thymohydroquinone dimethyl ether, is a phytochemical found in the essential oils of plants within the family Asteraceae. These essential oils, which contain the compound as a major component of the oil, have antifungal,[1] antibacterial,[2] and insecticidal[3] properties.
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| Names | |
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| IUPAC name
1,4-Dimethoxy-2-methyl-5-propan-2-ylbenzene | |
| Other names
Hydrothymoquinone dimethyl ether Thymoquinol dimethyl ether | |
| Identifiers | |
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CompTox Dashboard (EPA) |
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| Properties | |
| C12H18O2 | |
| Molar mass | 194.274 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Natural occurrence
2,5-Dimethoxy-p-cymene occurs in a variety of different plants' essential oils. Examples include:
- Ayapana triplinervis (92.8%)[4]
- Apium leptophyllum (50.7 to 80.24%)[5]
- Cyathocline purpurea (57.4%)[2]
- Arnica montana (32.6%)[6]
- Laggera crispata (32.2%)[7]
- Blumea perrottetiana (30.0%)[3]
- Eupatorium capillifolium (20.8%)[8]
- Sphaeranthus indicus (18.2%)[9]
- Limbarda crithmoides (16.4)[10]
- Bubonium imbricatum (16.2%)[1]
Chemical synthesis
2,5-Dimethoxy-p-cymene can be synthesized from carvacrol by aromatic halogenation followed by nucleophilic substitution with sodium methoxide and Williamson ether synthesis using methyl iodide.[11]
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See also
References
- Aliou, Hakim (2008). "Chemical composition and antifungal activity of Bubonium imbricatum volatile oil". Phytopathologia Mediterranea. 47 (1): 3–10. Archived from the original on 31 January 2017. Retrieved 19 January 2017.
- Joshi, Rajesh K. (2013). "Chemical constituents and antibacterial property of the essential oil of the roots of Cyathocline purpurea". Journal of Ethnopharmacology. 145 (2): 621–625. doi:10.1016/j.jep.2012.11.045. PMID 23220198.
- Owolabi, MS; L, Lajide; HE, Villanueva; WN, Setzer (2010). "Essential oil composition and insecticidal activity of Blumea perrottetiana growing in southwestern Nigeria". Natural Product Communications. 5 (7): 1135–1138. PMID 20734958.
- Anne Gauvin-Bialecki, Claude Marodon (November 2008). "Essential oil of Ayapana triplinervis from Reunion Island: A good natural source of thymohydroquinone dimethyl ether". Biochemical Systematics and Ecology. 36 (11): 853–858. doi:10.1016/j.bse.2008.09.006.
- Pande, C.; Tewari, G.; Singh, C.; Singh, S. (2011). "Essential oil composition of aerial parts of Cyclospermum leptophyllum (Pers.) Sprague ex Britton and P. Wilson". Natural Product Research. 25 (6): 592–595. doi:10.1080/14786419.2010.487190.
- Pljevljakušić, Dejan; Rančić, Dragana; Ristić, Mihailo; Vujisić, Ljubodrag; Radanović, Dragoja; Dajić-Stevanović, Zora (2012). "Rhizome and root yield of the cultivated Arnica montana L., chemical composition and histochemical localization of essential oil". Industrial Crops and Products. 39: 177–189. doi:10.1016/j.indcrop.2012.02.030.
- Ram S., Verma; Rajendra C., Padalia; Chandan S., Chanotiya; Amit, Chauhan; Anju, Yadav (2011). "Chemical investigation of the essential oil of Laggera crispata (Vahl) Hepper & Wood from India". Journal of the Serbian Chemical Society. 76 (4): 523–528. doi:10.2298/JSC100801048V.
- Tabanca, Nurhayat; Bernier, Ulrich R.; Tsikolia, Maia; Becnel, James J.; Sampson, Blair; Werle, Chris; Demirci, Betül; Can Ba, Kemal Hüsnü; Blythe, Eugene K.; Pounders, Cecil; Wedge, David E. (2010). "Eupatorium capillifolium Essential Oil: Chemical Composition, Antifungal Activity, and Insecticidal Activity". Natural Product Communications. 5 (9): 1409–1415. Retrieved 19 January 2017.
- Kaul, Pran N.; Rajeswara Rao, Bhaskaruni R.; Bhattacharya, Arun K.; Singh, Kamla; Mallavarapu, Gopal R.; Ramesh, S. (2005). "Essential Oil Composition of Sphaeranthus indicus L.". Journal of Essential Oil Research. 17 (4). doi:10.1080/10412905.2005.9698961.
- Andreani, Stéphane (2013). "Chemical Variability and Antioxidant Activity of Limbarda crithmoides L. Essential Oil from Corsica". Chemistry & Biodiversity. 10 (11): 2061–2077. doi:10.1002/cbdv.201300109.
- Fields, Shari L.; Soderberg, Bjora C. (1996). "Expedient Synthesis of Espintanol, p-Methoxycaracrol and Thymol Dimethyl Ether". Organic Preparations and Procedures International. 28 (2): 221–225. doi:10.1080/00304949609356526.
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