Alliin

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. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene. Garlic powder is not a source of alliin, nor is fresh garlic upon maceration, since the enzymatic conversion to allicin takes place in the order of seconds.

Alliin
Names
Systematic IUPAC name
(2R)-2-Amino-3-[(S)-(prop-2-ene-1-sulfinyl)]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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.291
EC Number
  • 209-118-9
KEGG
PubChem CID
UNII
  • InChI=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 Y
    Key: XUHLIQGRKRUKPH-DYEAUMGKSA-N Y
SMILES
  • C=CCS(=O)CC(C(=O)O)N
  • N[C@H](C(=O)O)C[S@@](=O)CC=C
Properties
C6H11NO3S
Molar mass 177.22 g/mol
Appearance White to off white crystalline powder
Melting point 163–165 °C (325–329 °F)
Soluble
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
NFPA 704 (fire diamond)
1
1
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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

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