• Alliin


    • Alliin
      Alliin skeletal view
      Alliin ball view
      IUPAC name
      (2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid
      Other names
      S-Allyl-L-cysteine sulfoxide
      556-27-4 N
      3D model (Jmol) Interactive image
      Interactive image
      ChEBI CHEBI:2596 N
      ChEMBL ChEMBL464166 N
      ChemSpider 7850537 YesY
      ECHA InfoCard 100.008.291
      Molar mass 177.22 g/mol
      Appearance White to off white crystalline powder
      Melting point 163–165 °C (325–329 °F)
      Safety data sheet External MSDS
      NFPA 704
      Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
      Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
      N  (what is YesYN ?)
      Infobox references

      Alliin /ˈæli.ɪn/ is a sulfoxide that is a natural constituent of fresh garlic. 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.

      Alliin has been found to affect immune responses in blood.

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

      The first reported synthesis, by Stoll and Seebeck in 1951, 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, allows stereospecific oxidation using conditions similar to the Sharpless asymmetric epoxidation. The chiral catalyst is produced from diethyl tartrate and titanium isopropoxide.

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    • Alliin