1,2-Dithiolane is an

organosulfur compound Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...

with the formula . It is also classified as a

heterocycle A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...

derived from

cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic compound, alicyclic hydrocarbon with chemical formula C5H10, C5H10 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and ...

by replacing two

methylene bridge In chemistry, a methylene bridge is part of a molecule with formula . The carbon atom is connected by single bonds to two other distinct atoms in the rest of the molecule. A methylene bridge is often called a methylene group or simply methylene, ...

s ( units) with a

disulfide In chemistry, a disulfide (or disulphide in British English) is a compound containing a functional group or the anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups. In inorg ...

group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially

lipoic acid Lipoic acid (LA), also known as α-lipoic acid, alpha-lipoic acid (ALA) and thioctic acid, is an organosulfur compound derived from caprylic acid (octanoic acid). ALA, which is made in animals normally, is essential for aerobic metabolism. It i ...

and its derivatives, are often essential for life. Several occur naturally. The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to

oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...

ization. In general, 1,3-dithiols are superior reductants relative to monothiols.

Natural occurrence

Many substituted 1,2-dithiolates are found in nature. The most common is

, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for

aerobic metabolism Cellular respiration is the process of oxidizing biological fuels using an inorganic electron acceptor, such as oxygen, to drive production of adenosine triphosphate (ATP), which stores chemical energy in a biologically accessible form. Cellu ...

in mammals. Some 1,2-dithiolane are found in some foods, such as

asparagusic acid Asparagusic acid is an organosulfur compound with the molecular formula C4H6O2S2 and systematically named 1,2-dithiolane-4-carboxylic acid. The molecule consists of a heterocyclic disulfide functional group (a 1,2- dithiolane) with a carbox ...

in asparagus. The 4-dimethylamino derivative nereistoxin was the inspiration for

insecticides Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. The major use of insecticides is in agriculture, but they are also used in home and garden settings, in ...

that act by blocking the

nicotinic acetylcholine receptor Nicotinic acetylcholine receptors, or nAChRs, are Receptor (biochemistry), receptor polypeptides that respond to the neurotransmitter acetylcholine. Nicotinic receptors also respond to drugs such as the agonist nicotine. They are found in the c ...

. 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. Asparagusic-acid.png, asparagusic acid Nereistoxin.svg, nereistoxin, from which insecticides including cartap and bensultap were derived Lipoic acid.svg, lipoic acid Gerrardine.svg, gerrardine, found in Cassipourea guianensis Charatoxin.svg, charatoxin, found in chara globuluris

Dithiolane-S-oxides

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

References

External links

{{cc
1,3-Dithiolane Reactions