|Preferred IUPAC name
2-Propene-1-sulfinothioic acid S-2-propenyl ester
3D model (JSmol)
|Molar mass||162.26 g·mol−1|
|Density||1.112 g cm−3|
|Melting point||<25 °C|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is part of a defense mechanism against attacks by pests on the garlic plant.
Structure and occurrence
Allicin features the thiosulfinate functional group, R-S(O)-S-R. The compound is not present in garlic unless tissue damage occurs, and is formed by the action of the enzyme alliinase on alliin. Allicin is chiral but occurs naturally only as a racemate. The racemic form can also be generated by oxidation of diallyl disulfide:
- (SCH2CH=CH2)2 + RCO3H → CH2=CHCH2S(O)SCH2CH=CH2 + RCO2H
Alliinase is irreversibly deactivated below pH 3; as such, allicin is generally not produced in the body from the consumption of fresh or powdered garlic. Furthermore, allicin can be unstable, breaking down within 16 hours at 23 °C.
Allicin is an oily, slightly yellow liquid that gives garlic its unique odor. It is a thioester of sulfenic acid and is also known as allyl thiosulfinate. Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.
In the biosynthesis of allicin (thio-2-propene-1-sulfinic acid S-allyl ester), cysteine is first converted into alliin (+ S-allyl-L-cysteine sulfoxide). The enzyme alliinase, which contains pyridoxal phosphate (PLP), cleaves alliin, generating allysulfenic acid, pyruvate, and ammonium. At room temperature allysulfenic acid is unstable and highly reactive, which cause two molecules of it to spontaneously combine in a dehydration reaction to form allicin.
Allicin has been studied for its potential to treat various kinds of multiple drug resistance bacterial infections, as well as viral and fungal infections in vitro, but as of 2016, the safety and efficacy of allicin to treat infections in people was unclear.
In a small clinical trial, a daily high dose of extracted allicin (20 times the amount in a garlic clove) showed effectiveness to prevent the common cold. A Cochrane review found this to be not sufficient to draw conclusions.
Allicin was discovered as part of efforts to create thiamine derivatives in the 1950s, mainly in Japan. Allicin became a model for medicinal chemistry efforts to create other thiamine disulfides. The results included sulbutiamine, fursultiamine (thiamine tetrahydrofurfuryl disulfide) and benfothiamine. These compounds are hydrophobic, easily pass from the intestines to the bloodstream, and are reduced to thiamine by cysteine or glutathione.:302
|Wikimedia Commons has media related to Allicin.|
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