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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:44:15 UTC
Update Date2019-07-23 06:14:48 UTC
HMDB IDHMDB0033963
Secondary Accession Numbers
  • HMDB33963
Metabolite Identification
Common NameAllicin
DescriptionAllicin, also known as allimin or allitridi, belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). Allicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Allicin is found, on average, in the highest concentration within soft-necked garlics. Allicin has also been detected, but not quantified in, several different foods, such as triticales, sunflowers, dates, pepper (c. frutescens), and napa cabbages. This could make allicin a potential biomarker for the consumption of these foods. Allicin was discovered as part of efforts to create thiamine derivatives in the 1950s, mainly in Japan. The compound is not present in garlic unless tissue damage occurs, and is formed by the action of the enzyme alliinase on alliin. Allicin is chiral but occurs naturally only as a racemate. The enzyme alliinase, which contains pyridoxal phosphate (PLP), cleaves alliin, generating allysulfenic acid (CH2CHCH2SOH), pyruvate, and ammonium. Its biological activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins.
Structure
Data?1563862488
Synonyms
ValueSource
2-Propene-1-sulfinothioic acid S-2-propenyl esterChEBI
Thio-2-propene-1-sulfinic acid S-allyl esterChEBI
2-Propene-1-sulfinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioate S-2-propenyl esterGenerator
2-Propene-1-sulphinothioic acid S-2-propenyl esterGenerator
Thio-2-propene-1-sulfinate S-allyl esterGenerator
Thio-2-propene-1-sulphinate S-allyl esterGenerator
Thio-2-propene-1-sulphinic acid S-allyl esterGenerator
2-Propene-1-sulfinic acid, thio-, S-allyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl esterHMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9ci)HMDB
AlliminHMDB
AllitridiHMDB
AllylthiosulfinateHMDB
Allylthiosulphinic acid allyl esterHMDB
DadsoHMDB
Diallyl disulfide-oxideHMDB
Diallyl thiosulfinateHMDB
Diallyldisulfid-S-oxidHMDB
S-2-Propenyl 2-propene-1-sulfinothioate, 9ciHMDB
S-Allyl 2-propene-1-sulfinothioateHMDB
S-Allyl acrylo-1-sulphinothioateHMDB
S-Allyl prop-2-ene-1-sulfinothioateHMDB
S-Prop-2-en-1-yl prop-2-ene-1-sulfinothioateHMDB
Chemical FormulaC6H10OS2
Average Molecular Weight162.273
Monoisotopic Molecular Weight162.017306322
IUPAC Name3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene
Traditional Nameallicin
CAS Registry Number539-86-6
SMILES
C=CCSS(=O)CC=C
InChI Identifier
InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2
InChI KeyJDLKFOPOAOFWQN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassThiosulfinic acid esters
Sub ClassNot Available
Direct ParentThiosulfinic acid esters
Alternative Parents
Substituents
  • Thiosulfinic acid ester
  • Allyl sulfur compound
  • Sulfenyl compound
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24 mg/mL at 10 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.13 g/LALOGPS
logP1.16ALOGPS
logP2.02ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity44.93 m³·mol⁻¹ChemAxon
Polarizability17.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-afcc42c2c1bd90b0e384Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0229-1900000000-a892e3c38e5a1381bfd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-8900000000-5679f84e236fe52171f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9100000000-938b07f1d7929cac2c10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-9700000000-734a318e76fb991aae76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9500000000-31a6285b63158ade86a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0096-9000000000-554fb97cc2ab4464f948Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11780
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012190
KNApSAcK IDC00001242
Chemspider ID58548
KEGG Compound IDC07600
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllicin
METLIN IDNot Available
PubChem Compound65036
PDB IDNot Available
ChEBI ID28411
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luo DQ, Guo JH, Wang FJ, Jin ZX, Cheng XL, Zhu JC, Peng CQ, Zhang C: Anti-fungal efficacy of polybutylcyanoacrylate nanoparticles of allicin and comparison with pure allicin. J Biomater Sci Polym Ed. 2009;20(1):21-31. doi: 10.1163/156856208X393473. [PubMed:19105898 ]
  2. Younis F, Mirelman D, Rabinkov A, Rosenthal T: S-allyl-mercapto-captopril: a novel compound in the treatment of Cohen-Rosenthal diabetic hypertensive rats. J Clin Hypertens (Greenwich). 2010 Jun;12(6):451-5. doi: 10.1111/j.1751-7176.2010.00270.x. [PubMed:20591093 ]
  3. Makheja AN, Bailey JM: Antiplatelet constituents of garlic and onion. Agents Actions. 1990 Mar;29(3-4):360-3. [PubMed:2111084 ]
  4. Hasan N, Siddiqui MU, Toossi Z, Khan S, Iqbal J, Islam N: Allicin-induced suppression of Mycobacterium tuberculosis 85B mRNA in human monocytes. Biochem Biophys Res Commun. 2007 Apr 6;355(2):471-6. Epub 2007 Feb 7. [PubMed:17303073 ]
  5. Park SY, Cho SJ, Kwon HC, Lee KR, Rhee DK, Pyo S: Caspase-independent cell death by allicin in human epithelial carcinoma cells: involvement of PKA. Cancer Lett. 2005 Jun 16;224(1):123-32. Epub 2004 Nov 14. [PubMed:15911108 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .