Vinyl dithiins

Egen-Schwind et al. (78) found that 1,2-vinyl dithiin, a component of oily preparations of garlic, accumulates in fatty tissues, whereas 1,3-vinyl dithiin is more hydrophilic and is rapidly eliminated from serum, kidney, and fat tissue. The latter compound was detected in rat liver over the first 24 hours... 

Fry/microwave Mainly diallyl disulfide, allyl methyl disulfide, vinyl dithiins... 

Macerated in oil Ihiosulfinate transformation compounds (vinyl dithiins, ajoenes, diallyl sulfide)... 

The oil of ether-extracted garlic homogenate has a similar qualitative composition to the oil-macerates, but it has a major advantage in being highly concentrated. It contains up to nine times the amount of the vinyl dithiins and allyl sulfides and four times the amount of the ajoenes found in typical commercial oil-macerates (Lawson, 1993). 

A number of garlic preparations have been used to study the effect of garlic on platelet aggregation (Lawson et al., 1992). It is thought that the effects of these commercial preparations are most likely attributable to allicin, ajoenes, vinyl dithiins... 

Garlic contains various sulfur-containing compounds, all of which are derived from allicin, which is formed from alliin by the action of allinase, which is released when garlic is chopped (Srivastava and Tyagi, 1993). Allicin then produces diallyl sulfide, diallyl disulfide, diallyl trisulfide, ajoenes, methyl allyl trisulfides, vinyl dithiins, and other sulfur compounds, depending on how the garlic is prepared. 

Elimination of other garlic components has also been studied. Allicin is metabolized in rat liver homogenate more rapidly than the vinyl dithiins, the main consitutents of oily preparations of garlic. As discussed in Section 9.7.2 Distribution, 1,2-vinyldithiin is lipophilic and tends to accumulate in fat, while 1,3-vinyldithiin is less lipophilic and more quickly eliminated from the serum, fat, and kidney. Both vinyldithiins can be detected in the serum, fat, and kidney using GC-MS for at least 24 h after oral administration (EgenSchwind et ah, 1992). 

Scheme (3). Formation of ajoenes and vinyl dithiins from allicin. (modified from Block et.al., 1986 [35]).

Dicyano-l,2-dithiete [53562-16-6] (14) is thought to be an intermediate when BAhr s Salt is oxidi2ed (64,65). If the oxidation is carried out in the presence of vinyl ethers, dihydro dithiins can be obtained in yields up to 60%. 

The cyclization involving Z-1,2-dimercaptoethenes, as with their benzo analogs, leads to 2-vinyl-l,4-dithiins 72 (69ZC184) rather than dithiacins. 

The violet thioacroleine readily dimerizes and can be isolated as a white crystalline mixture of 2-vinyl-1,3-dithiine( AHf ° =... 

Vinyl-3,6-dihydro-l,2-dithiin 2-oxide has been isolated as one of the main components from garlic Allium sativum) <2001MI867>. Its structure was elucidated by NMR and MS. 

Substituted 4,5-dihydro-l,2-dithiins were obtained as by-products in the copper-catalyzed ring expansion of vinyl... 

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