Article · Wikipedia archive · Last revised Jul 23, 2026

1,2-Dithiolane

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 with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally.

Last revised
Jul 23, 2026
Read time
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Source
Wikipedia ↗
1,2-Dithiolane
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Names
Preferred IUPAC name
1,2-Dithiolane
Identifiers
3D model (JSmol)
102454
ChEBI
ChemSpider
1029938
UNII
  • InChI=1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 checkY
    Key: MUZIZEZCKKMZRT-UHFFFAOYSA-N checkY
  • S1SCCC1
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 S2(CH2)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 unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally.1

The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization.2 In general, 1,3-dithiols are superior reductants relative to monothiols.3

Natural occurrence

Many substituted 1,2-dithiolates are found in nature.4 The most common is lipoic acid, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for aerobic metabolism in mammals.

Some 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus.5 The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that act by blocking the nicotinic acetylcholine receptor.6

Several alkyl-substituted 1,2-dithiolanes occur in the scent glands of skunks and related mammals. These include 3,3-dimethyl-, 3-propyl-, 3-ethyl-1,2-dithiolane, and others.4

Dithiolane-S-oxides

Isomers of brugierol source ↗

Many 1,2-dithiolanes can be oxidized to their S-oxides, which are chiral.4

References

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. Goodrow, Marvin H.; Olmstead, Marilyn M.; Musker, W. Kenneth (1983). "Preparation and X-Ray Crystal Structure of the Cyclic Dimer of 1,2-Dithiolane: 1,2,6,7-Tetrathiacyclodecane". Phosphorus and Sulfur and the Related Elements. 16 (3): 299–302. doi:10.1080/03086648308080483.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
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