1,2-Dithiolane

1,2-Dithiolane
Names
	IUPAC name 1,2-Dithiolane
Identifiers
CAS Number	557-22-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	102454
ChEBI	CHEBI:38226 ;
ChemSpider	71377;
Gmelin Reference	1029938
PubChem CID	79045;
UNII	6DE8XWQ974;
CompTox Dashboard (EPA)	DTXSID30204231 ;
	InChI InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N ;
	SMILES S1SCCC1;
Properties
Chemical formula	C3H6S2
Molar mass	106.20 g·mol−1
Related compounds
Related compounds	Ethane-1,2-dithiol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

1,2-Dithiolane is an organosulfur compound with the formula S₂(CH₂)₃. It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges (-CH
₂- units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is not important but substituted derivatives, especially lipoic acid and its derivatives, are important. Several occur in foods.^[1]

1,2-Dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to polymerization.^[2]

Substituted derivatives of 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus.^[3] The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that act by blocking the nicotinic acetylcholine receptor.^[4]

Lipoic acid is essential for aerobic metabolism in mammals and also has strong affinity with many metals including gold, molybdenum, and tungsten.^[5] Other 1,2-dithiolanes have relevance in nanomaterials such as gold nanoparticles or transition metal dichalcogenide monolayers (TMDs) (MoS₂ and WS₂).^[6]^[7]^[8]

asparagusic acid
nereistoxin, from which insecticides including cartap and bensultap were derived
lipoic acid

References

^ Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports. 9 (4): 257–333. doi:10.1080/01961779008048732.
^ Burns, John A.; Whitesides, George M. (1990). "Predicting the stability of cyclic disulfides by molecular modeling: Effective concentrations in thiol-disulfide interchange and the design of strongly reducing dithiols". Journal of the American Chemical Society. 112 (17): 6296–6303. doi:10.1021/ja00173a017.
^ Pelchat, M. L.; Bykowski, C.; Duke, F. F.; Reed, D. R. (2011). "Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study". Chemical Senses. 36 (1): 9–17. doi:10.1093/chemse/bjq081. PMC 3002398. PMID 20876394.
^ Casida, John E.; Durkin, Kathleen A. (2013). "Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects". Annual Review of Entomology. 58: 99–117. doi:10.1146/annurev-ento-120811-153645. PMID 23317040.
^ "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 27 August 2020.
^ Bilewicz, Renata; Więckowska, Agnieszka; Kruszewski, Marcin; Stępkowski, Tomasz; Męczynska-Wielgosz, Sylwia; Cichowicz, Grzegorz; Piątek, Piotr; Załubiniak, Dominika; Dzwonek, Maciej (2018-04-18). "Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit". RSC Advances. 8 (27): 14947–14957. Bibcode:2018RSCAd...814947D. doi:10.1039/C8RA01107A. ISSN 2046-2069. PMC 9079921. PMID 35541347.
^ Vallan, Lorenzo; Canton-Vitoria, Ruben; Gobeze, Habtom B.; Jang, Youngwoo; Arenal, Raul; Benito, Ana M.; Maser, Wolfgang K.; D’Souza, Francis; Tagmatarchis, Nikos (2018-10-17). "Interfacing Transition Metal Dichalcogenides with Carbon Nanodots for Managing Photoinduced Energy and Charge-Transfer Processes". Journal of the American Chemical Society. 140 (41): 13488–13496. doi:10.1021/jacs.8b09204. hdl:10442/16257. ISSN 0002-7863. PMID 30222336. S2CID 52291739.
^ Tagmatarchis, Nikos; Ewels, Christopher P.; Bittencourt, Carla; Arenal, Raul; Pelaez-Fernandez, Mario; Sayed-Ahmad-Baraza, Yuman; Canton-Vitoria, Ruben (2017-06-05). "Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion". npj 2D Materials and Applications. 1 (1): 13. doi:10.1038/s41699-017-0012-8. ISSN 2397-7132.

External links

1,3-Dithiolane Reactions

[1] Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports. 9 (4): 257–333. doi:10.1080/01961779008048732.

[2] Burns, John A.; Whitesides, George M. (1990). "Predicting the stability of cyclic disulfides by molecular modeling: Effective concentrations in thiol-disulfide interchange and the design of strongly reducing dithiols". Journal of the American Chemical Society. 112 (17): 6296–6303. doi:10.1021/ja00173a017.

[3] Pelchat, M. L.; Bykowski, C.; Duke, F. F.; Reed, D. R. (2011). "Excretion and perception of a characteristic odor in urine after asparagus ingestion: A psychophysical and genetic study". Chemical Senses. 36 (1): 9–17. doi:10.1093/chemse/bjq081. PMC 3002398. PMID 20876394.

[4] Casida, John E.; Durkin, Kathleen A. (2013). "Neuroactive Insecticides: Targets, Selectivity, Resistance, and Secondary Effects". Annual Review of Entomology. 58: 99–117. doi:10.1146/annurev-ento-120811-153645. PMID 23317040.

[5] "Lipoic acid". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis. 1 January 2019. Retrieved 27 August 2020.

[6] Bilewicz, Renata; Więckowska, Agnieszka; Kruszewski, Marcin; Stępkowski, Tomasz; Męczynska-Wielgosz, Sylwia; Cichowicz, Grzegorz; Piątek, Piotr; Załubiniak, Dominika; Dzwonek, Maciej (2018-04-18). "Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit". RSC Advances. 8 (27): 14947–14957. Bibcode:2018RSCAd...814947D. doi:10.1039/C8RA01107A. ISSN 2046-2069. PMC 9079921. PMID 35541347.

[7] Vallan, Lorenzo; Canton-Vitoria, Ruben; Gobeze, Habtom B.; Jang, Youngwoo; Arenal, Raul; Benito, Ana M.; Maser, Wolfgang K.; D’Souza, Francis; Tagmatarchis, Nikos (2018-10-17). "Interfacing Transition Metal Dichalcogenides with Carbon Nanodots for Managing Photoinduced Energy and Charge-Transfer Processes". Journal of the American Chemical Society. 140 (41): 13488–13496. doi:10.1021/jacs.8b09204. hdl:10442/16257. ISSN 0002-7863. PMID 30222336. S2CID 52291739.

[8] Tagmatarchis, Nikos; Ewels, Christopher P.; Bittencourt, Carla; Arenal, Raul; Pelaez-Fernandez, Mario; Sayed-Ahmad-Baraza, Yuman; Canton-Vitoria, Ruben (2017-06-05). "Functionalization of MoS 2 with 1,2-dithiolanes: toward donor-acceptor nanohybrids for energy conversion". npj 2D Materials and Applications. 1 (1): 13. doi:10.1038/s41699-017-0012-8. ISSN 2397-7132.

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