Wikipedia

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.

2,5-Dimethoxy-p-cymene
Names
Preferred IUPAC name
1,4-Dimethoxy-2-methyl-5-(propan-2-yl)benzene
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)
ChEMBL
ChemSpider
  • InChI=1S/C12H18O2/c1-8(2)10-7-11(13-4)9(3)6-12(10)14-5/h6-8H,1-5H3
    Key: VTRMVHBUTNPBTP-UHFFFAOYSA-N
  • CC1=CC(=C(C=C1OC)C(C)C)OC
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).

Natural occurrence

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

Chemical synthesis

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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]

See also

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References

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  1. ^ a b 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.
  2. ^ a b 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. ^ a b 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. doi:10.1177/1934578X1000500733. PMID 20734958. S2CID 43520689.
  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. PMID 21409720. S2CID 205836778.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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. doi:10.1177/1934578X1000500913. PMID 20922999. S2CID 18791244. Retrieved 19 January 2017.
  9. ^ 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): 453–454. doi:10.1080/10412905.2005.9698961. S2CID 93788240.
  10. ^ 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. PMID 24243615. S2CID 24089808.
  11. ^ 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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