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
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)	Interactive image
ChemSpider	4932489
PubChem CID	6427071
CompTox Dashboard (EPA)	DTXSID20423797
InChI 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
SMILES CC1=CC(=C(C=C1OC)C(C)C)OC
Properties
Chemical formula	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]

See also

• Thymoquinone

References

1. 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. 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. 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. 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. 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). doi:10.1080/10412905.2005.9698961.
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.
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.