Allyl sulfur compounds

The allyl sulfur compounds have two actions that may protect against the development of cancer  

They increase the metabolic clearance of potential carcinogens and their metabolites, by induction of glutathione S-transferases. 

The allyl sulfur compounds of garlic also have an anticoagulant action (by inhibiting platelet coagulability) and inhibit cholesterol synthesis by inactivating HMG-CoA reductase. 

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Reggelin M (2007) [2,3]-Sigmatropic Rearrangements of Allylic Sulfur Compounds. 275 1-65... 

Allylic phosphorus compounds Tris(tetrabutylammonium) pyrophosphate, 338 Allylsilanes t-Butyllithium, 58 Chlorotrimethylsilane-Lithium, 81 Lithium bis(dimethylphenylsilyl)-cuprate, 161 Methyllithium, 188 Trichlorosilane-t-Amines, 322 Allylic sulfur compounds (Phenylsulfonyl)allene, 247 Sodium benzenesulfinate, 289... 

The same is true for a number of other allylic sulfur compounds in which the sulfur carries a lithi--coordinating heteroatom. Coordination encourages reaction next to sulfur you might say it ces the lithium more at home there) and means that allyl sulfide alkylations can be made quite ioselective. The importance of this is probably not evident to you, but on p. 1268 you will meet a lthesis of the natural product nuciferal in which this principle is used—the key step will be the Ration of this allylic sulfide to give an 86% yield of the product with the alkyl group next to sulfur. 

A number of compounds found in foods of plant origin have potentially protective effects, although they cannot be considered to be dietary essentials they are variously known as phytonutrients, phytoceuticals, or nutraceuticals. Such compounds include allyl sulfur compounds, flavonoids, glucosinolates, and phytoestrogens. 

Members of the allium family (onions, garlic, and leeks) contain cysteine sulfoxide derivatives (allyl sulfur compounds), such as allicin and alliin (see Figure 14.9). When the plant cells are damaged, the enzyme alliinase is released from vacuoles and catalyzes the formation of thiosulfinates and thiols, including the lachrymator thiopropanal S-oxide. Their function in the plant is presumably to provide protection against attack by pests. 

Figure 14.9. Allyl sulfur compounds allicin and alllln. Relative molecular masses (Mr) allicin, 162.3 and alllln, 177.2.

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