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Alliin

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Alliin

Names
IUPAC name (2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid
Other names 3-(2-Propenylsulfinyl)alanine (S)-3-(2-Propenylsulfinyl)-L-alanine 3-((S)-Allylsulfinyl)-L-alanine S-Allyl-L-cysteine sulfoxide
Identifiers
CAS Number	556-27-4
ChEMBL	ChEMBL464166
ChemSpider	7850537
Jmol 3D model	Interactive image Interactive image
InChI[show]
SMILES[show]
Properties
Chemical formula	C6H11NO3S
Molar mass	177.22 g/mol
Appearance	White to off white crystalline powder
Melting point	163–165 °C (325–329 °F)
Solubility in water	Soluble
Hazards
Safety data sheet	External MSDS
NFPA 704	1 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Alliin /ˈæli.ɪn/ 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. Garlic has been used since antiquity as a therapeutic remedy for certain conditions now associated with oxygen toxicity, and, when this was investigated, garlic did indeed show strong antioxidant and hydroxyl radical-scavenging properties, it is presumed owing to the alliin contained within.^[2]

Alliin has been found to affect immune responses in blood.^[3]

Alliin was the first natural product found to have both carbon- and sulfur-centered stereochemistry.^[4]

Chemical synthesis[edit]

The first reported synthesis, by Stoll and Seebeck in 1951,^[5] begins the alkylation of L-cysteine with allyl bromide to form deoxyalliin. Oxidation of this sulfide with hydrogen peroxide gives both diastereomers of L-alliin, differing in the orientation of the oxygen atom on the sulfur stereocenter.

A newer route, reported by Koch and Keusgen in 1998,^[6] allows stereospecific oxidation using conditions similar to the Sharpless asymmetric epoxidation. The chiral catalyst is produced from diethyl tartrate and titanium isopropoxide