1,1-Ethanedithiol

Chemical compound CH3CH(SH)2 443340448 Ethane-1,1-dithiol 1,1-ethanedithiol.svg 120px Ethane-1,1-dithiol Ethane11dithiol-balls.png 120px Ball-and-stick model of ethane-1,1-dithiol Ethane-1,1-dithiol Methyldisulfanyl methane1,1-Ethanedithiol 248-103-1 33645 SC(S)C 31030 correct FDA 6E52Q3WL23 1S/C2H6S2/c1-2(3)4/h2-4H,1H3 DHBXNPKRAUYBTH-UHFFFAOYSA-N correct CAS 69382-62-3 2 6 2 Colorless liquid 0.83 g/cm3 12.97 g/L water Good solubility inmost organic solvents 71 1.37 07 Warning 302 312 332 261 264 270 271 280 301+312 302+352 304+312 304+340 312 322 330 363 501 thiols Ethanethiol; Methanedithiol; 1,2-Ethanedithiol; 1,1,1-Ethanetrithiol; 1-hydroxy-ethanethiol; propane-1,1-dithiol Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol. Use Flavouring uses of ethane-1,1-dithiol may include drinks, oil, gravy, soup, meat, fruit, seasonings, and snacks. Maximum concentrations in use that are generally recognised as safe (GRAS) is five parts per million (ppm) but typical uses are around 0.2 ppm.http://www.ift.org/knowledge-center/focus-areas/product-development-and-ingredient-innovations/~/media/Food%20Technology/pdf/2005/08/0805feat_gras22complete.pdf GRAS Flavoring Substances 22 Smith R. L. S. M. Cohen J. Doull V. J. Feron J. I. Goodman L. J. Marnett P. S. Portoghese W. J. Waddell B. M. Wagner T. B. Adams August 2005 Food Technology Institute of Food Technologists 47 1 December 2012 It is supplied as a 1% solution in ethanol, due to its strong offensive smell. In the diluted form with 4% ethyl acetate and ethanol the CAS number is 69382-62-3.http://www.perflavory.com/docs/doc1590721.html 1,1-ethane dithiol 1% in ethanol 94.5% / ethyl acetate 4% fragrance 69382-62-3 1 December 2012 2018-04-15 Toxicity may be due to metabolism products hydrogen sulfide and acetaldehyde, however as used it has a margin of safety of over 10,000,000.Meeting Joint FAO/WHO Expert Committee on Food Additives. Organization World Health Evaluation of Certain Food Additives and Contaminants: Sixty-eighth Report of the Joint FAO/WHO Expert Committee on Food Additives Geneva from 19 to 28 June 2007 http://whqlibdoc.who.int/publications/2007/9789241209472_eng.pdf 1 December 2012 2007 World Health Organization 9789241209472 108, 214–218 Other ways that it is modified in the body apart from hydrolysis is methylation to 1-methylsulfanyl-ethanethiol, oxidation of the sulfur to an ethyl sulfonate, glucuronidation of the sulfur, or combination with cysteine by way of a disulfide bridge. Identifiers Since it is used in the food industry there are codes issued by various authorities. It is identified as JECFA number 1660. The Flavor and Extract Manufacturers Association (FEMA) id is 4111. The European designation for the flavouring is Fl 12.293.European Food Safety Authority Scientific Opinion on Flavouring Group Evaluation 91, Revision 1 EFSA Journal 2011 9 12 2459 10.2903/j.efsa.2011.2459 free Natural occurrence It can be produced during fermentation of grapes.Fedrizzi Bruno Giuseppe Versini Roberto Ferrarini Fabio Finato Giorgio Nicolini Franco Magno 2011 1068 215–228 0097-6156 10.1021/bk-2011-1068.ch010 Sulfur Compounds in Still and Sparkling Wines and in Grappa: Analytical and Technological Aspects Volatile Sulfur Compounds in Food ACS Symposium Series 978-0-8412-2616-6 It is used as a food flavouring.http://www.codexalimentarius.net/input/download/standards/9/CXA_006e.pdf List of Codex Specification for Food Additives Joint FAO/WHO Expert Committee on Food Additives 2012 CAC/MISC 6 90 1 December 2012 It is found naturally in the scent of durian.http://phys.org/news/2012-11-scientists-substances-aroma-king-fruits.html Scientists sniff out the substances behind the aroma in the 'king of fruits' American Chemical Society 28 November 2012 1 December 2012Li Jia-Xiao Peter Schieberle Martin Steinhaus 2012 Characterization of the Major Odor-Active Compounds in Thai Durian (Durio zibethinus L. 'Monthong') by Aroma Extract Dilution Analysis and Headspace Gas Chromatography–Olfactometry Journal of Agricultural and Food Chemistry 60 45 11253–11262 0021-8561 10.1021/jf303881k 23088286 2012JAFC...6011253L Properties The nuclear magnetic resonance spectrum shows three environments for protons, in the ratio of 3:2:1 corresponding to CH3 SH and CH.http://www.fao.org/ag/agn/jecfa-flav/img/jecfa68/1660-hnmr.gif No 1660 Ethane-1,1-dithiol HNMR 2 December 2012September 2023 InternetArchiveBot yes Joint FAO/WHO Expert Committee on Food Additives Meeting Food and Agriculture Organization of the United Nations Compendium of Food Additive Specifications 2007 Food & Agriculture Org. 978-92-5-105866-4 112 https://books.google.com/books?id=NrOdaQ_gEm4C&dq=%22No+1660+Ethane-1,1-dithiol+HNMR%22&pg=PA112 en Reactions Ethane-1,1-dithiol has several reactions known that are important in white wine flavours. In the presence of oxygen, ethane-1,1-dithiol is converted to cis/trans-3,6-dimethyl-1,2,4,5-tetrathiane which has a rubbery aroma. This molecule has a ring with four sulfur atoms and two carbons, two ethane-1,1-dithiol molecules become linked at their sulfur atoms with the loss of hydrogen.Moreno-Arribas M. Victoria Polo Carmen Wine Chemistry and Biochemistry https://books.google.com/books?id=q_AkYRM-RR8C&pg=PA604 2 December 2012 2008-11-14 Springer 9780387741161 604– This can further oxidise to cis/trans-3,5-dimethyl-1,2,4-trithiolane, which has a meat-like odour. Ethane-1,1-dithiol reacts with hydrogen sulfide to form cis/trans-4,7-dimethyl-1,2,3,5,6-pentathiepane, a ring containing five sulfur atoms and two carbons. This has a meaty smell. Formation Ethane-1,1-dithiol can be formed in the reaction of acetaldehyde with hydrogen sulfide. 1-Hydroxyethanethiol is formed as an intermediary. See also Ethane-1,2-dithiol References External links Human Metabolome Database: Showing metabocard for Ethane-1,1-dithiol (HMDB0032253) http://www.hmdb.ca/metabolites/HMDB0032253 www.hmdb.ca http://www.fao.org/ag/agn/jecfa-flav/search.html?lang=en Food safety and quality: jecfa-flav 2012-12-01 2011-09-15 https://web.archive.org/web/20110915185631/http://www.fao.org/ag/agn/jecfa-flav/search.html?lang=en dead Drumm Terri D. Arthur M. Spanier 1991 Changes in the content of lipid autoxidation and sulfur-containing compounds in cooked beef during storage Journal of Agricultural and Food Chemistry 39 2 336–343 0021-8561 10.1021/jf00002a023 1991JAFC...39..336D Category:Alkanethiols Category:Flavors Category:Foul-smelling chemicals Category:Organic compounds with 2 carbon atoms