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Allicin

Not to be confused with Allysine or halicin.
Allicin
Structural formula of R-allicin
Structural formula of R-allicin
Ball and stick model of R-allicin
Ball and stick model of R-allicin
Names
Preferred IUPAC name
S-(Prop-2-en-1-yl) prop-2-ene-1-sulfinothioate
Other names
2-Propene-1-sulfinothioic acid S-2-propenyl ester
3-[(Prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
S-Allyl prop-2-ene-1-sulfinothioate
Identifiers
3D model (JSmol)
1752823
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.935 Edit this at Wikidata
EC Number
  • 208-727-7
KEGG
MeSH Allicin
UNII
  • InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2 checkY
    Key: JDLKFOPOAOFWQN-UHFFFAOYSA-N checkY
  • InChI=1/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
    Key: JDLKFOPOAOFWQN-UHFFFAOYAO
  • O=S(SC\C=C)C\C=C
  • C=CCSS(=O)CC=C
Properties
C6H10OS2
Molar mass 162.26 g·mol−1
Appearance Colourless liquid
Density 1.112 g cm−3
Melting point < 25 °C (77 °F; 298 K)
Boiling point decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Allicin is an organosulfur compound obtained from garlic and leeks.[1] When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic.[2] Allicin is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide.[3] Allicin is an antifeedant, i.e. the defense mechanism against attacks by pests on the garlic plant.[4]

Allicin is an oily, slightly yellow liquid that gives garlic its distinctive odor. It is a thioester of sulfenic acid. It is also known as allyl thiosulfinate.[5] Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.[6]

  1. ^ Block E (March 1985). "The Chemistry of Garlic and Onions". Scientific American. 252 (3): 114–9. Bibcode:1985SciAm.252c.114B. doi:10.1038/scientificamerican0385-114. PMID 3975593.
  2. ^ Kourounakis PN, Rekka EA (November 1991). "Effect on active oxygen species of alliin and Allium sativum (garlic) powder". Research Communications in Chemical Pathology and Pharmacology. 74 (2): 249–52. PMID 1667340.
  3. ^ Ilic D, Nikolic V, Nikolic L, Stankovic M, Stanojevic L, Cakic M (2011). "Allicin and related compounds: Biosynthesis, synthesis and pharmacological activity" (PDF). Facta Universitatis. 9 (1): 9–20. doi:10.2298/FUPCT1101009I.
  4. ^ Borlinghaus J, Albrecht F, Gruhlke MC, Nwachukwu ID, Slusarenko AJ (August 2014). "Allicin: chemistry and biological properties". Molecules. 19 (8): 12591–618. doi:10.3390/molecules190812591. PMC 6271412. PMID 25153873.
  5. ^ Nikolic V, Stankovic M, Nikolic L, Cvetkovic D (January 2004). "Mechanism and kinetics of synthesis of allicin". Die Pharmazie. 59 (1): 10–4. PMID 14964414.
  6. ^ Rabinkov A, Miron T, Konstantinovski L, Wilchek M, Mirelman D, Weiner L (February 1998). "The mode of action of allicin: trapping of radicals and interaction with thiol containing proteins". Biochimica et Biophysica Acta (BBA) - General Subjects. 1379 (2): 233–44. doi:10.1016/s0304-4165(97)00104-9. PMID 9528659.
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