2,5-Dimethoxy-''p''-cymene

2,5-Dimethoxy-p-cymene
Names
IUPAC name
1,4-Dimethoxy-2-methyl-5-propan-2-ylbenzene
Other names
Hydrothymoquinone dimethyl ether

Thymoquinol dimethyl ether
Thymohydroquinone dimethyl ether
1,4-Dimethoxy-2-isopropyl-5-methylbenzene
1,4-Dimethoxy-2-methyl-5-propan-2-ylbenzene

p-2,5-Dimethoxycymene
Identifiers
3D model (JSmol)
ChemSpider
Properties
C12H18O2
Molar mass 194.27 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

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.

Natural occurrence

2,5-Dimethoxy-p-cymene occurs in a variety of different plants' essential oils. Examples include:

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.[12]

See also

References

  1. 1 2 Aliou, Hakim (2008). "Chemical composition and antifungal activity of Bubonium imbricatum volatile oil". Phytopathologia Mediterranea. 47 (1): 3–10. Retrieved 19 January 2017.
  2. 1 2 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.
  3. 1 2 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ Helal, Iman E.; Galala, Amal A.; Saad, Hassan-Elrady A.; Halim, Ahmed F. (2015). "Chemical composition and α-amylase inhibitory activity of Apium leptophyllum essential oils". The Journal of American Science. 11 (4): 204–209. doi:10.7537/marsjas110415.23.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.
  12. ↑ 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.