1,2-Dioxetane

4-sided ring molecule (C2H2O4) changed changed 477204128 1,2-dioxetane.svg 1,2-dioxetane2.png 1,2-Dioxetane 1,2-Dioxacyclobutane Ethylene peroxidePeroxyethane correct chemspider 108850 1/C2H4O2/c1-2-4-3-1/h1-2H2 BVTJGGGYKAMDBN-UHFFFAOYAG O1OCC1 correct chemspider 1S/C2H4O2/c1-2-4-3-1/h1-2H2 correct chemspider BVTJGGGYKAMDBN-UHFFFAOYSA-N correct CAS 6788-84-7 correct FDA 142GQA523X 122029 C1OOC1 2 4 2 The chemical substance 1,2-dioxetane (systematically named 1,2-dioxacyclobutane, also known as ethylene peroxide or peroxyethane) is a heterocyclic, organic compound with formula C2O2H4, containing a ring of two adjacent oxygen atoms and two adjacent carbon atoms. It is therefore an organic peroxide, and can be viewed as a dimer of formaldehyde (COH2). Luminescence Chemiluminescence was first observed with lophine (triphenylimidazole). When in basic solution, this compound converts to the imidazolate, which reacts with oxygen to eventually give the 1,2-dioxetane. Fragmentation of the dioxetane gives the excited state of an anionic diamide.10.1002/bmc.226 Lophine derivatives as versatile analytical tools 2003 Nakashima Kenichiro Biomedical Chromatography 17 2–3 83–95 12717796 thumb|center|380px|Steps leading up to chemiluminescence of lophine. In the 1960s, 1,2-dioxetane were demonstrated as intermediates in the reactions responsible for the bioluminescence in fireflies, glow-worms, and other luminescent creatures. The luminescence of glowsticks and luminescent bangles and necklaces involves 1,2-dioxetanedione (C2O4), another dioxetane derivative that decomposes to carbon dioxide.Vacher Morgane Fdez. Galván Ignacio Ding Bo-Wen Schramm Stefan Berraud-Pache Romain Naumov Panče Ferré Nicolas Liu Ya-Jun Navizet Isabelle Roca-Sanjuán Daniel Baader Wilhelm J. Lindh Roland Chemi- and Bioluminescence of Cyclic Peroxides Chemical Reviews March 2018 10.1021/acs.chemrev.7b00649 29493234 118 15 6927–6974 10550/106201 free Other dioxetane derivatives are used in clinical analysis, where their light emission (which can be measured even at very low levels) allows chemists to detect very low concentrations of body fluid constituents.US Patent No. 5,330,900 to Tropix Inc. Derivatives In 1968 the first example of a stable dioxetane derivative was made at the University of Alberta in Edmonton: 3,3,4-trimethyl-1,2-dioxetane, prepared as a yellow solution in benzene. When heated to 333 K, it decomposed smoothly (rather than explosively, as many peroxides do) to acetone and acetaldehyde with the emission of pale blue light.Luminescence in the thermal decomposition of 3,3,4-trimethyl-1,2-dioxetane, Canadian Journal of Chemistry, Volume 47, p 709 (1969), K.R.Kopecky and C. Mumford The second example of a dioxetane derivative was made shortly after: the symmetrical compound 3,3,4,4-tetramethyl-1,2-dioxetane, obtained as pale yellow crystals that sublimed even when kept in the refrigerator. Benzene solutions of this compound also decomposed smoothly with the emission of blue light. By adding compounds that normally fluoresce in UV light the colour of the emitted light could be altered.Preparation and Thermolysis of Some 1,2-Dioxetanes, Canadian Journal of Chemistry, 1975, 53(8): 1103-1122, Karl R. Kopecky, John E. Filby, Cedric Mumford, Peter A. Lockwood, and Jan-Yih Ding.10.1139/v75-154 Carbon monoxide generation The dioxetane intermediate can release carbon monoxide and has been explored as a pro-drug. Peroxidation of heme at the alpha-methine bridge generates carbon monoxide and forms biliverdin as a non-enzymatic alternative pathway to heme oxygenaseBerk, Paul D.; Berlin, Nathaniel I. (1977). International Symposium on Chemistry and Physiology of Bile Pigments. U.S. Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health. pp. 27, 50. Lipid peroxidationHopper Christopher P. De La Cruz Ladie Kimberly Lyles Kristin V. Wareham Lauren K. Gilbert Jack A. Eichenbaum Zehava Magierowski Marcin Poole Robert K. Wollborn Jakob Wang Binghe 2020-12-23 Role of Carbon Monoxide in Host–Gut Microbiome Communication https://doi.org/10.1021/acs.chemrev.0c00586 Chemical Reviews 120 24 13273–13311 10.1021/acs.chemrev.0c00586 33089988 224824871 0009-2665 subscription Peroxidation of the reactive enol of alpha keto acids, such as the tautomer of phenylpyruvic acid at the benzylic carbon, can form a fluorescing 1,2-dioxetane to generate benzaldehyde and oxalic acid. Alternatively, a peroxylactone can form (alpha-keto-beta-peroxylactone) which also forms benzaldehyde but liberates carbon dioxide and carbon monoxide.Hopper Christopher P. Zambrana Paige N. Goebel Ulrich Wollborn Jakob 2021 A brief history of carbon monoxide and its therapeutic origins https://linkinghub.elsevier.com/retrieve/pii/S1089860321000367 Nitric Oxide en 111-112 45–63 10.1016/j.niox.2021.04.001 33838343 233205099 subscription See also 1,3-Dioxetane References Category:Organic peroxides Category:Dioxetanes Category:Organic compounds with 2 carbon atoms