Chemical Defense in Millipedes (Myriapoda, Diplopoda): Do Representatives of the Family Blaniulidae Belong to the ‘Quinone’ Clade? was written by Vujisic, Ljubodrag V.;Antic, Dragan Z.;Vuckovic, Ivan M.;Sekulic, Tatjana Lj.;Tomic, Vladimir T.;Mandic, Boris M.;Tesevic, Vele V.;Curcic, Bozidar P. M.;Vajs, Vlatka E.;Makarov, Slobodan E.. And the article was included in Chemistry & Biodiversity in 2014.Name: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione This article mentions the following:
The defensive secretions of 2 blaniulid millipedes, Nopoiulus kochii and Cibiniulus phlepsii, were characterized by GC-FID and GC/MS analyses, which showed the presence of a complex mixture of benzoquinones, hydroquinones, and oleates. Altogether, 13 compounds were identified. The major compound in the secretions of both analyzed species was 2-methyl-1,4-benzoquinone (toluquinone). The 2nd major constituent in the N. kochii secretion was 2-methyl-3,4-(methylenedioxy)phenol, while in that of C. phlepsii, it was 2-methoxy-3-methyl-1,4-benzoquinone. The defensive secretion of N. kochii also showed a high content of hydroquinones (13.5%) in comparison to that of C. phlepsii (0.8%). Hexyl oleate and octyl oleate were detected for the 1st time in defensive millipede fluids. The chem. composition of the defensive secretions supports the chemotaxonomic position of the family Blaniulidae in the quinone millipede clade. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Name: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione).
2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Name: 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem