1,2-Dithiolane
Chemical compound
From Wikipedia, the free encyclopedia
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 (âCH2â 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]
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| Names | |||
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| Preferred IUPAC name
1,2-Dithiolane | |||
| Identifiers | |||
3D model (JSmol) |
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| 102454 | |||
| ChEBI | |||
| ChemSpider | |||
| 1029938 | |||
PubChem CID |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C3H6S2 | |||
| Molar mass | 106.20 g·molâ1 | ||
| 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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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
Many 1,2-dithiolanes can be oxidized to their S-oxides, which are chiral.[4]
