Chemistry:1,2-Dithiolane

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1,2-Dithiolane
1,2-dithiolane-2D-skeletal.png
Dithiolane13d.png
Names
IUPAC name
1,2-Dithiolane
Identifiers
3D model (JSmol)
102454
ChEBI
ChemSpider
1029938
UNII
Properties
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).
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1,2-Dithiolane is an organosulfur compound with the formula S
2(CH
2)
3. It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges (-CH2- 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

  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. 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. https://lpi.oregonstate.edu/mic/dietary-factors/lipoic-acid. Retrieved 27 August 2020. 
  6. ↑ Bilewicz, Renata; Więckowska, Agnieszka; Kruszewski, Marcin; Stępkowski, Tomasz; Męczynska-Wielgosz, Sylwia; Cichowicz, Grzegorz; Piątek, Piotr; Załubiniak, Dominika et al. (2018-04-18). "Towards potent but less toxic nanopharmaceuticals – lipoic acid bioconjugates of ultrasmall gold nanoparticles with an anticancer drug and addressing unit" (in en). RSC Advances 8 (27): 14947–14957. doi:10.1039/C8RA01107A. ISSN 2046-2069. PMID 35541347. Bibcode: 2018RSCAd...814947D. 
  7. ↑ Vallan, Lorenzo; Canton-Vitoria, Ruben; Gobeze, Habtom B.; Jang, Youngwoo; Arenal, Raul; Benito, Ana M.; Maser, Wolfgang K.; D’Souza, Francis et al. (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. ISSN 0002-7863. PMID 30222336. http://zaguan.unizar.es/record/87809. 
  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" (in en). npj 2D Materials and Applications 1 (1): 13. doi:10.1038/s41699-017-0012-8. ISSN 2397-7132. 

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