Alliin

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title: "Alliin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["alpha-amino-acids", "sulfoxides", "sulfur-amino-acids", "nutrition", "allyl-compounds"] topic_path: "general/alpha-amino-acids" source: "https://en.wikipedia.org/wiki/Alliin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | verifiedrevid = 477317756 | Name = Alliin | ImageFile = L-alliin-2D-skeletal.png | ImageName = Alliin skeletal view | ImageFile1 = L-alliin-3D-balls.png | ImageName1 = Alliin ball view | SystematicName = (2R)-2-Amino-3-[(S)-(prop-2-ene-1-sulfinyl)]propanoic acid | OtherNames = 3-(2-Propenylsulfinyl)alanine (S)-3-(2-Propenylsulfinyl)-L-alanine 3-[(S)-Allylsulfinyl]-L-alanine S-Allyl-L-cysteine sulfoxide |Section1={{Chembox Identifiers | SMILES = C=CCS(=O)CC(C(=O)O)N | ChemSpiderID_Ref = | ChemSpiderID = 7850537 | ChEBI_Ref = | ChEBI = 2596 | ChEMBL_Ref = | ChEMBL = 464166 | PubChem = 9576089 | EC_number = 209-118-9 | UNII = 7I4L2D0E9G | KEGG = C08265 | SMILES1 = NC@HCS@@CC=C | StdInChI_Ref = | StdInChI = 1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = XUHLIQGRKRUKPH-DYEAUMGKSA-N | CASNo_Ref = | CASNo = 556-27-4 |Section2={{Chembox Properties | C=6 | H=11 | N=1 | O=3 | S=1 | Appearance = White to off white crystalline powder | Solubility = Soluble | MeltingPt = 163 - |Section7={{Chembox Hazards | ExternalSDS = External MSDS | NFPA-H = 1 | NFPA-F = 1 | NFPA-R = 0 | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases =

Alliin is a sulfoxide that is a natural constituent of fresh garlic.{{cite journal | author = Iberl, B | title = Quantitative Determination of Allicin and Alliin from Garlic by HPLC | journal = Planta Med. | volume = 56 | issue =3 | pages = 320–326 | year = 1990 | doi = 10.1055/s-2006-960969 | pmid = 17221429 | last2 = Winkler, G | last3 = Müller, B | last4 = Knobloch, K | bibcode = 1990PlMed..56..320I | s2cid = 30268881

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

Chemical synthesis

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.

:[[File:H2O2toAlliin.png|left|frameless|420 px]]

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.

Medical exploration

Garlic has been used since antiquity for conditions now associated with oxidative stress (production and accumulation of reactive oxygen species (ROS)). In an in vitro test, garlic powder showed antioxidant properties, and alliin showed good hydroxyl radical-scavenging effect.{{cite journal |author1=Kourounakis, PN |author2=Rekka, EA | title = Effect on active oxygen species of alliin and Allium sativum (garlic) powder | journal = Res. Commun. Chem. Pathol. Pharmacol. | volume = 74 | issue = 2 | pages = 249–252 | date=November 1991 | pmid = 1667340 | author = Salman, H | title = Effect of a garlic derivative (alliin) on peripheral blood cell immune responses | journal = Int. J. Immunopharmacol. | volume = 21 | issue = 9 | pages = 589–597 | date=September 1999 | pmid = 10501628 | doi = 10.1016/S0192-0561(99)00038-7 | last2 = Bergman | first2 = M | last3 = Bessler | first3 = H | last4 = Punsky | first4 = I | last5 = Djaldetti | first5 = M

References

References

  1. (2001). "Intake of Garlic and Its Bioactive Components". Oxford University Press (OUP).
  2. Block, E. (2009). "Garlic and Other Alliums: The lore and the science". [[Royal Society of Chemistry]].
  3. (1951). "Chemical investigations on alliin, the specific principle of garlic".
  4. (1998). "Diastereoselective synthesis of alliin by an asymmetric sulfur oxidation". Pharmazie.

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alpha-amino-acidssulfoxidessulfur-amino-acidsnutritionallyl-compounds