View source for Chemistry:2,5-Dimethoxy-p-cymene

{{DISPLAYTITLE:2,5-Dimethoxy-''p''-cymene}}
{{chembox
| Name = 2,5-Dimethoxy-''p''-cymene
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| ImageFile = 2,5-Dimethoxy-p-cymene.svg
| ImageSize = 
| PIN = 1,4-Dimethoxy-2-methyl-5-(propan-2-yl)benzene
| OtherNames = {{unbulleted list|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 }}
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo = 14753-08-3
| ChEMBL_Ref = 
| ChEMBL = 456933
| ChemSpiderID_Ref = 
| ChemSpiderID = 4932489
| StdInChI_Ref = 
| StdInChI = 1S/C12H18O2/c1-8(2)10-7-11(13-4)9(3)6-12(10)14-5/h6-8H,1-5H3
| StdInChIKey_Ref = 
| StdInChIKey = VTRMVHBUTNPBTP-UHFFFAOYSA-N
| PubChem = 6427071
| SMILES = CC1=CC(=C(C=C1OC)C(C)C)OC
}}
|Section2={{Chembox Properties
| C=12 | H=18 | O=2
| Appearance = 
| Density = 
| MeltingPtC = 
| BoilingPt = 
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = }}
}}

'''2,5-Dimethoxy-''p''-cymene''', or '''thymohydroquinone dimethyl ether''', is a [[Chemistry:Phytochemical|phytochemical]] found in the [[Chemistry:Essential oil|essential oil]]s of plants within the family ''[[Biology:Asteraceae|Asteraceae]]''. These essential oils, which contain the compound as a major component of the oil, have [[Chemistry:Antifungal|antifungal]],<ref name=imbricatum /> antibacterial,<ref name=Joshi />  and insecticidal<ref name=Blume /> properties.

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

* ''Ayapana triplinervis'' (92.8%)<ref>{{cite journal | author = Anne Gauvin-Bialecki, Claude Marodon | title = Essential oil of ''Ayapana triplinervis'' from Reunion Island: A good natural source of thymohydroquinone dimethyl ether | journal =  Biochemical Systematics and Ecology | volume = 36 | issue = 11 |date=November 2008 | pages = 853–858 | doi = 10.1016/j.bse.2008.09.006}}</ref>
* ''Apium leptophyllum'' (50.7 to 80.24%)<ref>{{cite journal|last1=Pande|first1=C.|last2=Tewari|first2=G.|last3=Singh|first3=C.|last4=Singh|first4=S.|title=Essential oil composition of aerial parts of Cyclospermum leptophyllum (Pers.) Sprague ex Britton and P. Wilson|journal=Natural Product Research|date=2011|volume=25|issue=6|pages=592–595|doi=10.1080/14786419.2010.487190|pmid=21409720|s2cid=205836778}}</ref>
* ''Cyathocline purpurea'' (57.4%)<ref name=Joshi>{{cite journal|last1=Joshi|first1=Rajesh K.|title=Chemical constituents and antibacterial property of the essential oil of the roots of Cyathocline purpurea|journal=Journal of Ethnopharmacology|date=2013|volume=145|issue=2|pages=621–625|doi=10.1016/j.jep.2012.11.045|pmid=23220198}}</ref>
* ''[[Biology:Arnica montana|Arnica montana]]'' (32.6%)<ref>{{cite journal|last1=Pljevljakušić|first1=Dejan|last2=Rančić|first2=Dragana|last3=Ristić|first3=Mihailo|last4=Vujisić|first4=Ljubodrag|last5=Radanović|first5=Dragoja|last6=Dajić-Stevanović|first6=Zora|title=Rhizome and root yield of the cultivated Arnica montana L., chemical composition and histochemical localization of essential oil|journal=Industrial Crops and Products|date=2012|volume=39|pages=177–189|doi=10.1016/j.indcrop.2012.02.030}}</ref>
* ''Laggera crispata'' (32.2%)<ref>{{cite journal|last1=Ram S.|first1=Verma|last2=Rajendra C.|first2=Padalia|last3=Chandan S.|first3=Chanotiya|last4=Amit|first4=Chauhan|last5=Anju|first5=Yadav|title=Chemical investigation of the essential oil of Laggera crispata (Vahl) Hepper & Wood from India|journal=Journal of the Serbian Chemical Society|date=2011|volume=76|issue=4|pages=523–528|doi=10.2298/JSC100801048V|doi-access=free}}</ref>
* ''Blumea perrottetiana'' (30.0%)<ref name=Blume>{{cite journal|last1=Owolabi|first1=MS|last2=L|first2=Lajide|last3=HE|first3=Villanueva|last4=WN|first4=Setzer|title=Essential oil composition and insecticidal activity of Blumea perrottetiana growing in southwestern Nigeria|journal=Natural Product Communications|date=2010|volume=5|issue=7|pages=1135–1138|doi=10.1177/1934578X1000500733|pmid=20734958|s2cid=43520689|doi-access=free}}</ref>
* ''[[Biology:Eupatorium capillifolium|Eupatorium capillifolium]]'' (20.8%)<ref>{{cite journal|last1=Tabanca|first1=Nurhayat|last2=Bernier|first2=Ulrich R.|last3=Tsikolia|first3=Maia|last4=Becnel|first4=James J.|last5=Sampson|first5=Blair|last6=Werle|first6=Chris|last7=Demirci|first7=Betül|last8=Can Ba|first8=Kemal Hüsnü|last9=Blythe|first9=Eugene K.|last10=Pounders|first10=Cecil|last11=Wedge|first11=David E.|title=Eupatorium capillifolium Essential Oil: Chemical Composition, Antifungal Activity, and Insecticidal Activity|journal=Natural Product Communications|date=2010|volume=5|issue=9|pages=1409–1415|doi=10.1177/1934578X1000500913|pmid=20922999|s2cid=18791244|url=http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=1975&context=usdaarsfacpub|access-date=19 January 2017|doi-access=free}}</ref>
* ''[[Biology:Sphaeranthus indicus|Sphaeranthus indicus]]'' (18.2%)<ref>{{cite journal|last1=Kaul|first1=Pran N.|last2=Rajeswara Rao|first2=Bhaskaruni R.|last3=Bhattacharya|first3=Arun K.|last4=Singh|first4=Kamla|last5=Mallavarapu|first5=Gopal R.|last6=Ramesh|first6=S.|title=Essential Oil Composition of Sphaeranthus indicus L.|journal=Journal of Essential Oil Research|date=2005|volume=17|issue=4|pages=453–454|doi=10.1080/10412905.2005.9698961|s2cid=93788240}}</ref>
* ''[[Biology:Limbarda crithmoides|Limbarda crithmoides]]'' (16.4)<ref>{{cite journal|last1=Andreani|first1=Stéphane|title=Chemical Variability and Antioxidant Activity of Limbarda crithmoides L. Essential Oil from Corsica|journal=Chemistry & Biodiversity|date=2013|volume=10|issue=11|pages=2061–2077|doi=10.1002/cbdv.201300109|pmid=24243615|s2cid=24089808}}</ref>
* ''Bubonium imbricatum'' (16.2%)<ref name=imbricatum>{{cite journal|last1=Aliou|first1=Hakim|title=Chemical composition and antifungal activity of Bubonium imbricatum volatile oil|journal=Phytopathologia Mediterranea|date=2008|volume=47|issue=1|pages=3–10|url=http://www.fupress.net/index.php/pm/article/view/2541|access-date=19 January 2017|archive-url=https://web.archive.org/web/20170131190751/http://www.fupress.net/index.php/pm/article/view/2541|archive-date=31 January 2017|url-status=dead}}</ref>

==Chemical synthesis==
2,5-Dimethoxy-''p''-cymene can be synthesized from [[Chemistry:Carvacrol|carvacrol]] by aromatic [[Chemistry:Halogenation#Halogenation of aromatic compounds|halogenation]] followed by [[Chemistry:Nucleophilic substitution|nucleophilic substitution]] with [[Chemistry:Sodium methoxide|sodium methoxide]] and [[Chemistry:Williamson ether synthesis|Williamson ether synthesis]] using [[Chemistry:Methyl iodide|methyl iodide]].<ref>{{cite journal|last1=Fields|first1=Shari L.|last2=Soderberg|first2=Bjora C.|title=Expedient Synthesis of Espintanol, p-Methoxycaracrol and Thymol Dimethyl Ether|journal=Organic Preparations and Procedures International|date=1996|volume=28|issue=2|pages=221–225|doi=10.1080/00304949609356526}}</ref>

==See also==
*[[Chemistry:Thymoquinone|Thymoquinone]]

==References==
{{reflist}}

{{DEFAULTSORT:Dimethoxy-p-cymene, 2,5-}}
[[Category:Hydroquinone ethers]]
[[Category:Fungicides]]
[[Category:Insecticides]]
[[Category:Alkyl-substituted benzenes]]
[[Category:Isopropyl compounds]]
[[Category:Methoxy compounds]]

{{Sourceattribution|2,5-Dimethoxy-p-cymene}}