Diallyl disulphide

Diallyl disulphide, (C3H5)S.S(C3H6), is a light yellow oil of garlic odour, found to the extent of about 60 per cent, in oil of garlic. It is a liquid of specific gravity 1-023, and boils at 80° to 81° at 16 mm. pressure. 

Garlic Allium sativum Diallyl disulphide Callus 14% of explant [57, 58]... 

Germain E, Auger J, Ginies C, Siess MH, Teyssier C. In vivo metabolism of diallyl disulphide in the rat identiflcation of two new metabolites. Xenobiotica 2002 32 1127-1138. 

Allyl disulphide (diallyl disulphide) [2179-57-9] M 146.3, 58-59°/5mm, b 79-81°/20mm, 138-139°/atm, d 1.01, no 1-541. Purified by fractional distn until their molar refractivities are in uniformly good agreement with the calculated values [JACS 69 1710 7947]. Also purified by gas chromatography [retention times JOC 2A 175 1959 UV JCS 395 7949]. 

Group 20 is a nice collection of wonderful sulphur compounds. Disulphides such as diallyl disulphide (Flavis 12.008, FEMA 2028) with onion- and garlic-like notes are followed by extremely powerful mercaptans like the grapefruit compound p-l-men-thene-thiol (Flavis 12.085, FEMA 3700). In addition, thiols with tropical sulphury notes complete the picture of interesting molecules. 

Vliet, J . Am. Chem. Soc., 1924, 46, 1307. Diallyl disulphide Allyl disulphide)... 

Pushpendran CK, Devasagayam TP, Chintalwar GJ, Banerji A, Eapen J (1980) The metabolic fate of [35S]-diallyl disulphide in mice. Experientia 36(8) 1000-1001 Nagae S, Ushijima M, Hatono S, Imai J, Kasuga S, Matsuura H, Itakura Y, Higashi Y (1994) Pharmacokinetics of the garlic compound S-allylcysteine. Planta Med 60(3) 214-217. 

Mathew, P.T. and August , K.T. 1973. Studies on the effect of allicin (diallyl disulphide-oxide) on alloxan diabetes. I. Hypoglycemic action and enhancement of serum insulin effect and glycogen synthesis. Indian JBiochem Biophys 20(3) 209-212. 

The human metabolism of these sulphur compounds is complex and far from understood. Moreover, due to the complexity and number of potential products, it is difficult to generalize. Several compounds probably conjugate with glutathione post-absorption, and are metabolized via the mercapturic acid pathways, in a similar manner to isothiocyanates. N-acetyl-S-aUyl-L-cysteine (allylmercapturic acid), derived from diallyl disulphide, has been detected in urine from humans who have consumed garlic (de Rooji et al. 1996). The characteristic breath and perspiration odours foimd following garlic consumption are... 

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