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Revision as of 16:57, 8 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi		Latest revision as of 05:54, 6 January 2025 edit OAbot (talk | contribs)Bots441,761 editsm Open access bot: hdl updated in citation with #oabot.
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	{{chembox		{{chembox
	| verifiedrevid = 443705168		|verifiedrevid = 443707568
	|ImageFileL1=1,2-dithiolane-2D-skeletal.png		|ImageFileL1=1,2-dithiolane-2D-skeletal.png
	|ImageSizeL1=75px		|ImageSizeL1=75px
	|ImageFileR1=Dithiolane13d.png		|ImageFileR1=Dithiolane13d.png
	|ImageSizeR1=100px		|ImageSizeR1=100px
	|ImageFileL2=1,3-dithiolane-2D-skeletal.png
	|ImageSizeL2=75px
	|ImageFileR2=Dithiolane23d.png		|ImageFileR2=Dithiolane23d.png
	|ImageSizeR2=100px		|ImageSizeR2=100px
			|ImageCaption2 = 1,2-Dithiolane (top row) and 1,3-dithiolane (bottom row)
	|IUPACName=Dithiolane		|IUPACName=1,2-Dithiolane
	|OtherNames=1,2-dithiolane, 1,3-dithiolane
			|OtherNames=
	|Section1= {{Chembox Identifiers		|Section1={{Chembox Identifiers
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	|CASNo_Ref = {{cascite|correct|CAS}}
⚫	| ChemSpiderID = 71377
		⚫	|CASNo=557-22-2
⚫	| InChI = 1/C3H6S2/c1-2-4-5-3-1/h1-3H2
			| Beilstein = 102454
⚫	| InChIKey = MUZIZEZCKKMZRT-UHFFFAOYAH
		⚫	|ChEBI = 38226
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| StdInChI = 1S/C3H6S2/c1-2-4-5-3-1/h1-3H2
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| ChemSpiderID2 = 71377
	| StdInChIKey = MUZIZEZCKKMZRT-UHFFFAOYSA-N
			| Gmelin = 1029938
⚫	| CASNo=
	| PubChem = 79045		|PubChem = 79045
			|UNII = 6DE8XWQ974
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	|InChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| ChEBI = 38226
		⚫	|InChI = 1S/C3H6S2/c1-2-4-5-3-1/h1-3H2
⚫	| SMILES = S1SCCC1
		⚫	|InChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	|InChIKey = MUZIZEZCKKMZRT-UHFFFAOYSA-N
		⚫	|SMILES = S1SCCC1
		⚫	}}
		⚫	|Section2={{Chembox Properties
			|C=3 | H=6 | S=2
		⚫	}}
		⚫	|Section8={{Chembox Related
			| OtherCompounds = ]
	}}		}}
⚫	|Section2= {{Chembox Properties
	| Formula=C<sub>3</sub>H<sub>6</sub>S<sub>2</sub>
	| MolarMass=
	| Appearance=
	| Density=
	| MeltingPt=
	| BoilingPt=
	| Solubility=
	| pKa =
	| pKb =
⚫	}}
	|Section3= {{Chembox Hazards
	| MainHazards=
	| FlashPt=
	| Autoignition=
⚫	}}
⚫	| Section8 = {{Chembox Related
	| OtherCpds = ]
	}}
	}}		}}
	A '''dithiolane''' is a ] ] derived from ] by replacing two ] groups with ] groups. The parent compounds are '''1,2-dithiolane''' and '''1,3-dithiolane'''.		'''1,2-Dithiolane''' is an ] with the formula {{chem2|S2(CH2)3}}. It is also classified as a ] derived from ] by replacing two ]s (-{{chem|CH|2}}- units) with a ] group. ] is an isomer. The parent molecule is not important but substituted derivatives, especially ] and its derivatives, are important. Several occur in foods.<ref>{{cite journal |doi=10.1080/01961779008048732 |title=Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties |year=1990 |last1=Teuber |first1=Lene |journal=Sulfur Reports |volume=9 |issue=4 |pages=257–333}}</ref>
			1,2-Dithiolane is the disulfide derived from ]. It is however unstable with respect to ]ization.<ref>{{cite journal|doi=10.1021/ja00173a017 |title=Predicting the stability of cyclic disulfides by molecular modeling: Effective concentrations in thiol-disulfide interchange and the design of strongly reducing dithiols |date=1990 |last1=Burns |first1=John A. |last2=Whitesides |first2=George M. |journal=Journal of the American Chemical Society |volume=112 |issue=17 |pages=6296–6303 }}</ref>
	1,2-Dithiolanes, such as ], are cyclic ].
			Substituted derivatives of 1,2-dithiolane are found in some foods, such as ] in asparagus.<ref>{{cite journal|title = Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study|first1 = M. L.|last1 = Pelchat|first2 = C.|last2 = Bykowski|first3 = F. F.|last3 = Duke|first4 = D. R.|last4 = Reed|journal = ]|year = 2011|volume = 36|issue = 1|pages = 9–17|doi = 10.1093/chemse/bjq081|pmid=20876394|pmc=3002398}}</ref> The 4-dimethylamino derivative ] was the inspiration for ] that act by blocking the ].<ref>{{cite journal |doi=10.1146/annurev-ento-120811-153645 |title=Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects |year=2013 |last1=Casida |first1=John E. |last2=Durkin |first2=Kathleen A. |journal=Annual Review of Entomology |volume=58 |pages=99–117 |pmid=23317040}}</ref>
	1,3-Dithiolanes are important as ]s for ] compounds, since they are inert to a wide range of conditions. Reacting a carbonyl group with ] converts it to a 1,3-dithiolane, as detailed below.
			] is essential for ] in mammals and also has strong affinity with many metals including gold, molybdenum, and tungsten.<ref>{{cite web |title=Lipoic acid |url=https://lpi.oregonstate.edu/mic/dietary-factors/lipoic-acid |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis |accessdate=27 August 2020 |date=1 January 2019}}</ref> Other 1,2-dithiolanes have relevance in nanomaterials such as gold nanoparticles or ] (TMDs) (] and ]).<ref>{{Cite journal|last1=Bilewicz|first1=Renata|last2=Więckowska|first2=Agnieszka|last3=Kruszewski|first3=Marcin|last4=Stępkowski|first4=Tomasz|last5=Męczynska-Wielgosz|first5=Sylwia|last6=Cichowicz|first6=Grzegorz|last7=Piątek|first7=Piotr|last8=Załubiniak|first8=Dominika|last9=Dzwonek|first9=Maciej|date=2018-04-18|title=Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit|journal=RSC Advances|language=en|volume=8|issue=27|pages=14947–14957|doi=10.1039/C8RA01107A|pmid=35541347 |pmc=9079921 |bibcode=2018RSCAd...814947D |issn=2046-2069|doi-access=free}}</ref><ref>{{Cite journal|last1=Vallan|first1=Lorenzo|last2=Canton-Vitoria|first2=Ruben|last3=Gobeze|first3=Habtom B.|last4=Jang|first4=Youngwoo|last5=Arenal|first5=Raul|last6=Benito|first6=Ana M.|last7=Maser|first7=Wolfgang K.|last8=D’Souza|first8=Francis|last9=Tagmatarchis|first9=Nikos|date=2018-10-17|title=Interfacing Transition Metal Dichalcogenides with Carbon Nanodots for Managing Photoinduced Energy and Charge-Transfer Processes|journal=Journal of the American Chemical Society|volume=140|issue=41|pages=13488–13496|doi=10.1021/jacs.8b09204|issn=0002-7863|pmid=30222336|hdl=10442/16257|s2cid=52291739 |url=http://zaguan.unizar.es/record/87809|hdl-access=free}}</ref><ref>{{Cite journal|last1=Tagmatarchis|first1=Nikos|last2=Ewels|first2=Christopher P.|last3=Bittencourt|first3=Carla|last4=Arenal|first4=Raul|last5=Pelaez-Fernandez|first5=Mario|last6=Sayed-Ahmad-Baraza|first6=Yuman|last7=Canton-Vitoria|first7=Ruben|date=2017-06-05|title=Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion|journal=npj 2D Materials and Applications|language=en|volume=1|issue=1|pages=13|doi=10.1038/s41699-017-0012-8|issn=2397-7132|doi-access=free|hdl=10261/367520|hdl-access=free}}</ref>
	]
			<gallery>
			Asparagusic-acid.png|asparagusic acid
			Nereistoxin.svg|nereistoxin, from which insecticides including cartap and bensultap were derived
			Lipoic acid.svg|lipoic acid
			</gallery>
			==References==
			{{reflist}}
	==External links==		==External links==
			{{cc}}
	*		*
⚫	]
		⚫	]
	]
	]