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Allicin is an organosulfur compound obtained from garlic and leeks. [1] When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. [2] Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. [3]
Alliin / ˈ æ l i. ɪ n / is a sulfoxide that is a natural constituent of fresh garlic. [1] It is a derivative of the amino acid cysteine.When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic.
Allicin garlic. Alliin garlic. Allyl isothiocyanate horseradish, mustard, wasabi. Syn-propanethial-S-oxide cut onions. Indoles. Indole-3-carbinol cabbage, kale ...
The sulfur compound allicin, produced by crushing or chewing fresh garlic, [10] produces other sulfur compounds: ajoene, allyl polysulfides, and vinyldithiins. [2] Aged garlic lacks allicin, but may have some activity due to the presence of S-allylcysteine. Some people suffer from allergies to garlic and other species of Allium. [2]
The reaction sequence that forms ajoene (2 in the diagram) involves two molecules of allicin. First, one allicin molecule (1 in the diagram) fragments to form 2-propenesulfenic acid and thioacrolein. These two react in separate stages with another allicin molecule by way of a conjugated thiocationic intermediate. [1]
In garlic, an alliinase enzyme acts on the chemical alliin converting it into allicin. The process involves two stages: elimination of 2-propenesulfenic acid from the amino acid unit (with dehydroalanine as a byproduct), and then condensation of two of the sulfenic acid molecules. Reaction scheme for the conversion: cysteine → alliin → allicin
When crushed and then analyzed using a DART ion source, elephant garlic has been shown to produce both allicin, found in garlic, and syn-propanethial-S-oxide (onion lachrymatory factor), found in onion and leek, but absent in garlic, consistent with the classification of elephant garlic as a closer relative of leek than of garlic.
Compounds like allicin and ajoene are responsible for the odor of garlic. Lenthionine contributes to the flavor of shiitake mushrooms. Volatile organosulfur compounds also contribute subtle flavor characteristics to wine, nuts, cheddar cheese, chocolate, coffee, and tropical fruit flavors. [30]
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