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1,2-Dithiolane

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1,2-Dithiolane
Names
IUPAC name 1,2-Dithiolane
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 102454
ChEBI
ChemSpider
Gmelin Reference 1029938
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N
SMILES
  • S1SCCC1
Properties
Chemical formula C3H6S2
Molar mass 106.20 g·mol
Related compounds
Related compounds Ethane-1,2-dithiol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

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

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

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

  • asparagusic acid asparagusic acid
  • nereistoxin, from which insecticides including cartap and bensultap were derived nereistoxin, from which insecticides including cartap and bensultap were derived
  • lipoic acid 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. 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. hdl:10261/367520. ISSN 2397-7132.

External links

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