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Diallyl disulfide and the related trisulfide are produced by decomposition of allicin, which is released upon breaking the cells of the Alliaceae plants, especially garlic. The diallyl disulfide yield is the highest for the steam distillation of garlic bulbs which contain about 2 wt.% of diallyl disulfide-rich oil. Diallyl disulfide can also be ...
Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. [3] Allicin is an antifeedant, i.e. the defense mechanism against attacks by pests on the garlic plant. [4] Allicin is an oily, slightly yellow liquid that gives garlic its distinctive odor. It is a thioester of sulfenic acid.
Whereas the former mechanism acts via skin rubbing which progresses into damage, the major cause of the latter is the chemical diallyl disulfide (DADS), [2] together with related compounds allyl propyl disulfide and allicin. These chemicals occur in oils of plants of the genus Allium, including garlic, onion and leek. [3]
The major volatile compounds responsible for garlic breath are allyl methyl sulfide, allyl methyl disulfide, allyl mercaptan, diallyl disulfide, dimethyl disulfide and methyl mercaptan, along with minor amounts of dimethyl selenide. [1] [2] [3] Various other sulfur compounds are also produced when allicin in garlic is broken down in the stomach ...
When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene. [2]
Allicin, S-benzyl phenylmethanethiosulfinate, and related thiosulfinates show radical-trapping antioxidant activity associated with easy formation of sulfenic acids [12] The acyclic thiosulfinates from Allium and Brassica species possess antimicrobial, antiparasitic, antitumor and cysteine protease inhibitory activity while the natural 1,2-dithiolane-1-oxides are growth inhibitors.
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The process of cooking garlic removes allicin, thus mellowing its spiciness. [16] Allicin, along with its decomposition products diallyl disulfide and diallyl trisulfide, are major contributors to the characteristic odor of garlic, with other allicin-derived compounds, such as vinyldithiins and ajoene. [2]