3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene

• ChemBase ID: 125681
• Molecular Formular: C6H10OS2
• Molecular Mass: 162.273
• Monoisotopic Mass: 162.01730694
• SMILES: O=S(SCC=C)CC=C
• Canonical SMILES: C=CCSS(=O)CC=C
• InChI: InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
• InChIKey: JDLKFOPOAOFWQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
• IUPAC Systematic name: 3-[(Prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
• IUPAC Traditional name: allicin
• Synonyms: Allicin; 2-Propene-1-sulfinothioic Acid S-2-Propen-1-yl Ester; Allicin; Allimed; Alliosan; Allisure Liquid; Diallyl Thiosulfinate; Thio-2-propene-1-sulfinic Acid S-Allyl Ester

Database IDs

• CAS Number: 539-86-6
• EC Number: 208-727-7
• Beilstein Number: 1752823
• PubChem SID: 162220031
• PubChem CID: 65036
• CHEBI ID: 28411
• CHEMBL: 359965
• Chemspider ID: 58548
• IUPHAR ligand ID: 2419
• KEGG ID: C07600
• MeSH Name: Allicin
• Unique Ingredient Identifier: 3C39BY17Y6
• Wikipedia Title: Allicin

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.0214
• LogD (pH = 7.4): 2.0214
• Log P: 2.0214
• Molar Refractivity: 44.9326 cm^3
• Polarizability: 18.012882 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Colourless liquid
• Melting Point: <25 °C
• Boiling Point: decomposes
• Density: 1.112 g cm^-3

DETAILS

Toronto Research Chemicals - A543500

Allicin is naturally formed by the action of the enzyme allicinase on alliin when the tissue of the garlic bulb is disrupted. Allicin shows antibacterial activity.

REFERENCES

• Yamada, Y., et al.: Antimicrob. Agents Chemother., 11, 743 (1977)
• Mayeux, P.R., et al.: Agents Actions, 25, 182 (1977)
• Freeman, F., et al.: J. Agric. Food Chem., 43, 2332 (1977)
• Macpherson, L.J., et al.: Curr. Biol., 15, 929 (1977)