Structure via PubChem · Public domain (PubChem)
(+)-L-alliin
Sign in to saveAlso known as (2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid, (S)-S-Allyl-L-cysteine sulfoxide, (+)-Alliin
Alliin 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
Chemical data
- Formula
- C6H11NO3S
- Molecular weight
- 177.22 g/mol
- IUPAC name
- (2R)-2-amino-3-[(S)-prop-2-enylsulfinyl]propanoic acid
- SMILES
- C=CC[S@](=O)C[C@@H](C(=O)O)N
- InChIKey
- XUHLIQGRKRUKPH-DYEAUMGKSA-N
- XLogP
- -3.5
- Polar surface area
- 99.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 177.045964212
Show 4 more facts
- chemical formula
- C₆H₁₁NO₃S
- canonical SMILES
- C=CCS(=O)CC(C(=O)O)N
- isomeric SMILES
- C=CC[S@](=O)C[C@@H](C(=O)O)N
- found in taxon
- Allium ursinum
via Wikidata · CC0
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Encyclopedic overview
3 sectionsContents
- Chemical synthesis
- Medical exploration
- References
Alliin 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 was the first natural product found to have both carbon- and sulfur-centered stereochemistry.
Excerpted from Wikipedia’s “(+)-L-alliin” article, available under the CC BY-SA 4.0 licence.