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	{{chembox		{{chembox
	| verifiedrevid = 443339224		|verifiedrevid = 443340448
	| Name = 1,2-Ethanedithiol		|Name = Ethane-1,1-dithiol
			|ImageFileL1 = 1,1-ethanedithiol.svg
	| ImageFile = Ethanedithiol.png
			|ImageSizeL1 = 120px
	| ImageSize = 150px
			|ImageNameL1 = Ethane-1,1-dithiol
	| ImageName = 1,2-Ethanedithiol
	| ImageFile1 = Ethane-1,2-dithiol-3D-balls.png		|ImageFileR1 = Ethane11dithiol-balls.png
			|ImageSizeR1 = 120px
	| ImageSize1 = 150px
	| ImageName1 = Ball-and-stick model of ethane-1,2-dithiol		|ImageNameR1 = Ball-and-stick model of ethane-1,1-dithiol
	| ImageFile2 = Ethane-1,2-dithiol-3D-vdW.png		|PIN = Ethane-1,1-dithiol
			|OtherNames = Methyldisulfanyl methane<br />1,1-Ethanedithiol
	| ImageSize2 = 150px
			|Section1={{Chembox Identifiers
	| ImageName2 = Space-filling model of ethane-1,2-dithiol
			|EINECS = 248-103-1
	| IUPACName = Ethane-1,2-dithiol
			|PubChem = 33645
	| OtherNames = Dimercaptoethane<br />1,2-Ethanedithiol
			|SMILES = SC(S)C
	| Section1 = {{Chembox Identifiers
			|ChemSpiderID_Ref =
	| UNII_Ref = {{fdacite|correct|FDA}}
			|ChemSpiderID = 31030
	| UNII = 92T634FLAR
			|UNII_Ref = {{fdacite|correct|FDA}}
	| SMILES = SCCS
			|UNII = 6E52Q3WL23
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|StdInChI = 1S/C2H6S2/c1-2(3)4/h2-4H,1H3
	| ChemSpiderID = 13865015
			|StdInChIKey = DHBXNPKRAUYBTH-UHFFFAOYSA-N
	| InChI = 1/C2H6S2/c3-1-2-4/h3-4H,1-2H2
			|CASNo_Ref = {{cascite|correct|CAS}}
	| InChIKey = VYMPLPIFKRHAAC-UHFFFAOYAA
			|CASNo = 69382-62-3
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			}}
	| StdInChI = 1S/C2H6S2/c3-1-2-4/h3-4H,1-2H2
			|Section2={{Chembox Properties
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| C=2 | H=6 | S=2
	| StdInChIKey = VYMPLPIFKRHAAC-UHFFFAOYSA-N
			|Appearance = Colorless liquid
	| CASNo_Ref = {{cascite|correct|CAS}}
			|Density = 0.83 g/cm<sup>3</sup>
	| CASNo = 540-63-6
			|Solubility = 12.97 g/L
	| RTECS = KI3325000
			|Solvent = water
	}}
			|SolubleOther = Good solubility in<br />most organic solvents
	| Section2 = {{Chembox Properties
			|BoilingPtC = 71
	| C=2|H=6|S=2
			|RefractIndex = 1.37
	| Appearance = Colorless liquid
			}}
	| Density = 1.123 g/cm³
			|Section7={{Chembox Hazards
	| Solubility = Slightly sol
			|GHSPictograms= {{GHS07}}
	| Solvent = other solvents
			|GHSSignalWord = Warning
	| SolubleOther = Good solubility in<br />most organic solvents
			|HPhrases = {{H-phrases|302|312|332}}
	| MeltingPtC = -41
			|PPhrases = {{P-phrases|261|264|270|271|280|301+312|302+352|304+312|304+340|312|322|330|363|501}}
	| BoilingPtC = 146
			}}
	| Boiling_notes = 46 mmHg
			|Section8={{Chembox Related
	| pKa = ~11
			| OtherFunction_label = ]s
	| pKb =
			| OtherFunction = ]; ]; ]; ]; ]; ]
	| Viscosity =
			}}
	| RefractIndex = 1.5589 (D-line, 25 °C)
	}}
	| Section3 = {{Chembox Structure
	| Dipole =
	}}
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| EUClass = Toxic ('''T''')
	| NFPA-H = 2
	| NFPA-F = 2
	| NFPA-R =
	| FlashPt = 50 °C
	| RPhrases = {{R10}} {{R22}}
	| SPhrases = {{S16}}
	}}
	| Section8 = {{Chembox Related
	| Function = ]s
	| OtherFunctn = ]; ]; ]; ]
	}}
	}}		}}
	'''1,2-Ethanedithiol''' is a colorless liquid with the formula C<sub>2</sub>H<sub>4</sub>(SH)<sub>2</sub>. It has a very characteristic odor which is compared by many people to rotten cabbage. It is a common building block in ] and an excellent ligand for metal ions.		'''Ethane-1,1-dithiol''' is an ] with formula CH<sub>3</sub>CH(SH)<sub>2</sub>. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a ].
	==Preparation==		==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.<ref name="Smith">{{cite web|url=http://www.ift.org/knowledge-center/focus-areas/product-development-and-ingredient-innovations/~/media/Food%20Technology/pdf/2005/08/0805feat_gras22complete.pdf|title=GRAS Flavoring Substances 22|last1=Smith|first1=R. L.| first2=S. M.| last2=Cohen| first3=J.| last3=Doull| first4=V. J.| last4=Feron| first5=J. I.| last5=Goodman| first6=L. J.| last6=Marnett| first7=P. S.| last7=Portoghese| first8=W. J.| last8=Waddell| first9=B. M.| last9=Wagner| first10=T. B.| last10=Adams|date=August 2005|work=Food Technology|publisher=Institute of Food Technologists |page=47|accessdate=1 December 2012}}</ref> It is supplied as a 1% solution in ethanol, due to its strong offensive smell.<ref name="MeetingOrganization2007"/> In the diluted form with 4% ethyl acetate and ethanol the CAS number is 69382-62-3.<ref>{{cite web|url=http://www.perflavory.com/docs/doc1590721.html|title=1,1-ethane dithiol 1% in ethanol 94.5% / ethyl acetate 4% fragrance 69382-62-3|accessdate=1 December 2012|date=2018-04-15}}</ref> Toxicity may be due to metabolism products ] and ], however as used it has a margin of safety of over 10,000,000.<ref name="MeetingOrganization2007">{{cite book|last1=Meeting|first1=Joint FAO/WHO Expert Committee on Food Additives.|last2=Organization|first2=World Health|title=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|url=http://whqlibdoc.who.int/publications/2007/9789241209472_eng.pdf|accessdate=1 December 2012|year=2007|publisher=World Health Organization|isbn=9789241209472|pages=108, 214–218}}</ref> 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, ] of the sulfur, or combination with ] by way of a disulfide bridge.<ref name="MeetingOrganization2007"/>
	1,2-Ethanedithiol is commercially available. It can be prepared by the action of ] on ] followed by ].<ref>{{OrgSynth | author = Speziale, A. J. | title = Ethanedithiol | collvol = 4 | collvolpages = 401 | year = 1963 | prep = cv4p0401}}</ref>
	==Applications==		===Identifiers===
			Since it is used in the food industry there are codes issued by various authorities. It is identified as JECFA number 1660.<ref name="faowho"/> The ] (FEMA) id is 4111.<ref name="Smith"/> The European designation for the flavouring is Fl 12.293.<ref>{{cite journal|last=European Food Safety Authority|title=Scientific Opinion on Flavouring Group Evaluation 91, Revision 1|journal=EFSA Journal |year=2011 |volume=9|issue=12 |page=2459|doi=10.2903/j.efsa.2011.2459|doi-access=free}}</ref>
	This compound is widely used in organic chemistry because it reacts with ]s and ]s to give 1,3-]s, which are useful intermediates.
	<ref>R. E. Conrow "Ethanedithiol" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289}}</ref>
			==Natural occurrence==
	::C<sub>2</sub>H<sub>4</sub>(SH)<sub>2</sub> + RR'CO → C<sub>2</sub>H<sub>4</sub>S<sub>2</sub>CRR' + H<sub>2</sub>O
			It can be produced during fermentation of grapes.<ref>{{cite book|last=Fedrizzi|first=Bruno|author2=Giuseppe Versini|author3=Roberto Ferrarini|author4=Fabio Finato|author5=Giorgio Nicolini|author6= Franco Magno|year=2011|volume=1068|pages=215–228|issn=0097-6156|doi=10.1021/bk-2011-1068.ch010|chapter=Sulfur Compounds in Still and Sparkling Wines and in Grappa: Analytical and Technological Aspects|title=Volatile Sulfur Compounds in Food|series=ACS Symposium Series|isbn=978-0-8412-2616-6}}</ref> It is used as a food flavouring.<ref name="faowho">{{cite web|url=http://www.codexalimentarius.net/input/download/standards/9/CXA_006e.pdf|title=List of Codex Specification for Food Additives|last=Joint FAO/WHO Expert Committee on Food Additives|year=2012|work=CAC/MISC 6|page=90|accessdate=1 December 2012}}</ref>
			It is found naturally in the scent of ].<ref>{{cite web|url=http://phys.org/news/2012-11-scientists-substances-aroma-king-fruits.html|title=Scientists sniff out the substances behind the aroma in the 'king of fruits'|last=American Chemical Society|date=28 November 2012|accessdate=1 December 2012}}</ref><ref>{{cite journal|last=Li|first=Jia-Xiao|author2=Peter Schieberle|author3=Martin Steinhaus|year=2012|title=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=Journal of Agricultural and Food Chemistry|volume=60|issue=45|pages=11253–11262|issn=0021-8561|doi=10.1021/jf303881k|pmid=23088286}}</ref>
	]
			==Properties==
	Other 1,2- and 1,3-dithiols undergo this reaction to give related 1,3-dithiolanes and 1,3-dithianes (six-membered rings). ]s such as ] undergo analogous reactions to 1,3-]s and 1,3-]s. One distinguishing feature of the dithiolanes and dithianes derived from aldehydes is that the methyne group can be deprotonated and the resulting carbanion alkylated.
			The nuclear magnetic resonance spectrum shows three environments for protons, in the ratio of 3:2:1 corresponding to CH<sub>3</sub> SH and CH.<ref>{{cite web|url=http://www.fao.org/ag/agn/jecfa-flav/img/jecfa68/1660-hnmr.gif|title=No 1660 Ethane-1,1-dithiol HNMR|accessdate=2 December 2012}}{{Dead link|date=September 2023 |bot=InternetArchiveBot |fix-attempted=yes }}</ref><ref>{{cite book |author1=Joint FAO/WHO Expert Committee on Food Additives Meeting |author2=Food and Agriculture Organization of the United Nations |title=Compendium of Food Additive Specifications |date=2007 |publisher=Food & Agriculture Org. |isbn=978-92-5-105866-4 |page=112 |url=https://books.google.com/books?id=NrOdaQ_gEm4C&dq=%22No+1660+Ethane-1,1-dithiol+HNMR%22&pg=PA112 |language=en}}</ref>
			===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.<ref name="Moreno-ArribasPolo2008">{{cite book|last1=Moreno-Arribas|first1=M. Victoria|last2=Polo|first2=Carmen|title=Wine Chemistry and Biochemistry|url=https://books.google.com/books?id=q_AkYRM-RR8C&pg=PA604|accessdate=2 December 2012|date=2008-11-14|publisher=Springer|isbn=9780387741161|pages=604–}}</ref> This can further oxidise to ''cis''/''trans''-3,5-dimethyl-1,2,4-trithiolane which has a meat-like odour.<ref name="Moreno-ArribasPolo2008"/>
			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.<ref name="Moreno-ArribasPolo2008"/>
			===Formation===
			Ethane-1,1-dithiol can be formed in the reaction of ] with ]. ] is formed as an intermediary.<ref name="Moreno-ArribasPolo2008"/>
			== See also ==
			*]
	==References==		==References==
	<references />		<references/>
			==External links==
	{{DEFAULTSORT:Ethanethiol, 1,2-}}
			* {{cite web |title=Human Metabolome Database: Showing metabocard for Ethane-1,1-dithiol (HMDB0032253) |url=http://www.hmdb.ca/metabolites/HMDB0032253 |website=www.hmdb.ca}}
	]
			* {{cite web| url= http://www.fao.org/ag/agn/jecfa-flav/search.html?lang=en | title = Food safety and quality: jecfa-flav }}
	]
			* {{cite journal|last=Drumm|first=Terri D.|author2=Arthur M. Spanier|year=1991|title=Changes in the content of lipid autoxidation and sulfur-containing compounds in cooked beef during storage|journal=Journal of Agricultural and Food Chemistry|volume=39|issue=2|pages=336–343|issn=0021-8561|doi=10.1021/jf00002a023}}
	]
			{{DEFAULTSORT:Ethanedithiol, 1,1-}}
	]
			]
	]
			]
	]
			]