Diallyl disulfide

Diallylsulfonium salts undergo intramolecular allylic rearrangement with strong bases to yield 1,5-dienes after reductive desulfurization. The straight-chain 1,5-dienes may be obtained by double sulfur extrusion with concomitant allylic rearrangements from diallyl disulfides. The first step is achieved with phosphines or phosphites, the second with benzyne. This procedure is especially suitable for the synthesis of acid sensitive olefins and has been used in oligoisoprene synthesis (G.M. Blackburn, 1969). 

Self-Test 4.11B The Codex Ebers, an Egyptian medical papyrus, describes the use of garlic as an antiseptic. Chemists today have verified that the oxide of diallyl disulfide... 

Five known natural product HDAC inhibitors can be consumed in the human diet butyrate, diallyl disulfide (DADS), flavones, pomiferin, and sulforaphane (SFN). These compounds are found in fiber, garlic, broccoli, and various fruits. The first clinical use of HDAC inhibitors come from the butyrate class. 

Fig. 2. The chemical structure of (a) prodrug diallyl disulfide (DADS), (b) aUyl mercaptan, and (c) s-allylmercaptocysteine.

Myzak MC, Dashwood RH. (2006) Histone deacetylases as targets for dietary cancer preventive agents Lessons learned with bntyrate, diallyl disulfide, and snlforaphane. Current Drug Targets 7 443 52. 

Lea MA, Randolph VM, Patel M. (1999) Increased acetylation of histones induced by diallyl disulfide and structurally related molecules. Int J Oncol 15 347-352. 

Lea MA, Randolph VM. (2001) Induction of histone acetylation in rat liver and hepatoma by organosulfur compounds including diallyl disulfide. Anticancer Res 21 2841-2845. 

Diallyl disulfide [2179-57-9] is an essential odor component of garlic oil [233]. 

Recently, Germain et al. (90) studied the in vivo metabolism of diallyl disulfide (DADS), a garlic compound claimed to have anticarcinogenic effects. After oral administration of a single dose of 200mg/kg, metabolites were measured in the stomach, liver, plasma, and urine by GC coupled with MS over 15 days. DADS was detected in almost all analyzed tissues within the first hours. In addition, the metabolites allylmercaptan (AM) and allyl methyl sulfide (AMS) were detected. The Cmav of the metabolites were higher than that of DADS (1.46 pg/mL). The %ax for DADS was estimated to be less than one hour, whereas this time increased to 24 hours for AM and AMS (90). 

N.A. Alliin, iodine, diallyl trisulfide, 2-vinyl-4h-l,3-dithin, ajoene, linoleic acid, diallyl disulfide, scordinins, selenium.98 99 107 511 Reduce serum cholesterol, lower blood pressure, and platelet aggregation. It is anticancer, antimicrobial, antithrombotic. 

Self-Test 4.10B The Codex Ebers, an Egyptian medical papyrus, describes the use of garlic to treat many ailments, including the cleansing of wounds. Chemists today have discovered that the oxide of diallyl disulfide (the volatile compound responsible for garlic odor) is a powerful antibacterial agent more potent against typhoid than penicillin. At 177°C and 200 Torr, a sample of diallyl disulfide vapor has a density of 1.04 g-L 1. What is the molar mass of diallyl disulfide ... 

Nucleophilic reaction of Et3N with diallyl disulfide has been found to differ from that with diallyl sulfide in being very much more exothermic and also autocatalytic.14 Possible mechanisms were discussed. EHMO calculations have been performed for... 

Among well-known spice allergens are diallyl disulfide and Allicin (garlic allergens, Allium sativum), eugol (nutmeg, cloves, and Jamaica pepper), cinnamic aldehyde (cinnamon), dipentene (caraway, cardamom, and spearmint), and linalool (basilica, coriander) (Kanerva 2002). 

Sulfur-containing compounds. These are not derived from the terpenes. They have very pungent smells, e.g. diallyl disulfide found in garlic. 

Oxathiin 2,2-dioxides (sultones) (e.g., 150) are obtained by the addition of sulfur trioxide to dienes or by ringclosing metathesis (RCM) of sulfonates using the second-generation Grubbs ruthenium catalyst (Scheme 75) . The same catalyst was also successfully employed in the RCM of diallyl disulfide 151 which led quantitatively to 3,6-dihydro-l,2-dithiin 152 (Scheme 76) <20020L1767>. 

Garlic, Allium sativum L., is a species in the onion family, Alliaceae. Onion, shallot, and leek are close relatives. Garlic has been used throughout history for both culinary and medicinal purposes. It has a pungent hot sensation that mellows and sweetens considerably with cooking. A large number of sulfur compounds contribute to the smell and taste of members of the onion family. Diallyl disulfide and diallyl sulfide are... 

Diallyl disulfide Allium sativum (bulb, garlic oil) (Liliaceae) OD-R (garlic)... 

Diallyl disulfide (alkene sulfide) Allium cepa (onion), A. sativum (garlic) (Liliaceae) [bulb] SLOX (competitive)... 

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