Chemotaxonomic potential of exocrine alkyl esters in julid millipedes (Diplopoda: Julidae: Cylindroiulini) was written by Bodner, Michaela;Vagalinski, Boyan;Raspotnig, Guenther. And the article was included in Biochemical Systematics and Ecology in 2018.Synthetic Route of C9H10O4 This article mentions the following:
There are numerous chemotaxonomic studies on arthropods, but such are largely missing for millipedes. This appears curious since particularly in millipedes, the major taxa are clearly distinctive by different exocrine products, such as alkaloids (Glomerida), terpenoids (Polyzoniida), phenolics and cyanogens (Polydesmida), and benzoquinones (Juliformia). However, there is low within-taxon variation of the chems. mentioned which – in almost invariable blends – characterize the particular taxa. The Julida, for instance, one of the three orders of Juliformia, typically produce uniformly composed benzoquinonic secretion profiles across most species, not showing enough heterogeneity for chemotaxonomy. Recently, however, a new class of julid exocrine products, namely complex bends of alkyl esters has been reported. We here tested the chemotaxonomic potential of these compounds by performing a comprehensive study on alkyl esters across the julid tribe Cylindroiulini. Exocrine secretions of 20 species from all five cylindroiuline genera (Allajulus, Cylindroiulus, Enantiulus, Kryphioiulus, Styrioiulus) were analyzed by gas chromatog. – mass spectrometry. Apart from typical benzoquinones, 33 alkyl esters and 1 alkenyl ester belonging to hexyl-, octyl-, octenyl- and nonyl-esters with saturated and mono-unsaturated acid moieties ranging from C13 – C18 were detected. Only two species (Cylindroiulus caeruleocinctus and C. luridus) exhibited no esters at all. Ester profiles appeared to be specific, indicating five major chem. groups in cylindroiulines, characterized by specific ester arrangements. We here provide evidence for (i) the widespread occurrence of alkyl esters in the Julidae, (ii) their high specificity, (iii) their intra-species stability, (iv) along with sufficient inter-species variability, rendering them promising novel tools for millipede chemotaxonomy. In the experiment, the researchers used many compounds, for example, 2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7Synthetic Route of C9H10O4).
2,3-Dimethoxy-5-methylcyclohexa-2,5-diene-1,4-dione (cas: 605-94-7) belongs to ethers. Of all the functional groups, ethers are the least reactive ones. Ether bonds are quite stable towards bases, oxidizing agents and reducing agents. But on the other hand, ethers undergo cleavage by reaction with acids. 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.Synthetic Route of C9H10O4
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem