cis-Ajoene (CHEM025319)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 22:19:12 UTC
Update Date2016-11-09 01:18:03 UTC
Accession NumberCHEM025319
Identification
Common Namecis-Ajoene
ClassSmall Molecule
DescriptionAjoene is found in onion-family vegetables. Ajoene is isolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer properties Ajoene is a chemical compound available from garlic (Allium sativum). The name (and pronunciation) is derived from "ajo", the Spanish word for garlic. It is found as a mixture of two isomers, E-, and Z- 4,5,9-trithiadodeca-1,6,11-triene 9-oxide. Ajoene, an unsaturated disulfide, is formed from the bonding of three allicin molecules. Allicin is a sulfinyl compound that gives garlic its strong odor and flavor. The release of allicin occurs after a garlic clove is crushed or finely chopped. Subsequent formation of ajoene occurs when allicin is dissolved in various solvents including edible oils. Ajoene is also found in garlic extract. Ajoene is most stable and most abundant in macerate of garlic (chopped garlic in edible oil)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9ciHMDB
2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfideHMDB
4,5,9-Trithia-1,6,11-dodecatriene 9-oxideHMDB
4,5,9-Trithiadodeca-1,6,11-triene 9-oxideHMDB
Allyl 3-allylsulfinyl-1-propenyl disulfideHMDB
Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenylHMDB
trans-AjoeneHMDB
Chemical FormulaC9H14OS3
Average Molecular Mass234.402 g/mol
Monoisotopic Mass234.021 g/mol
CAS Registry Number92285-01-3
IUPAC Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
Traditional Name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
SMILESC=CCSS\C=C/CS(=O)CC=C
InChI IdentifierInChI=1S/C9H14OS3/c1-3-6-11-12-7-5-9-13(10)8-4-2/h3-5,7H,1-2,6,8-9H2/b7-5-
InChI KeyIXELFRRANAOWSF-ALCCZGGFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sulfoxides. Sulfoxides are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
KingdomOrganic compounds
Super ClassOrganosulfur compounds
ClassSulfoxides
Sub ClassNot Available
Direct ParentSulfoxides
Alternative Parents
Substituents
  • Allyl sulfur compound
  • Sulfoxide
  • Organic disulfide
  • Sulfenyl compound
  • Sulfinyl compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP2.58ALOGPS
logP1.66ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)16.01ChemAxon
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability24.81 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-38a71ef9ab244c72057dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-7890000000-11928f7c30159af165e8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9600000000-c607fc1496412765e8c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-a2836ecdf1469af5047cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0016-6960000000-e17a4526d3baecc4e388Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9300000000-d62719e8491d22e01b5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f72-9300000000-e0cce5cae13d413bf294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-5940000000-2ff7b7a62d176c1fb383Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-9400000000-cb9a19f42f5eeb7c8908Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-c468260d51fc7a1b3b0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9310000000-a37b89564227f0a2bab0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-9200000000-110a3f385d2a123a74caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-9100000000-1d553532a99796a2a70bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0033566
FooDB IDFDB003580
Phenol Explorer IDNot Available
KNApSAcK IDC00052510
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAjoene
Chemspider ID8056824
ChEBI ID80707
PubChem Compound ID9881148
Kegg Compound IDC16757
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Naganawa R, Iwata N, Ishikawa K, Fukuda H, Fujino T, Suzuki A: Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. Appl Environ Microbiol. 1996 Nov;62(11):4238-42.
2. Ledezma E, Apitz-Castro R: [Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]. Rev Iberoam Micol. 2006 Jun;23(2):75-80.
3. Urbina JA, Marchan E, Lazardi K, Visbal G, Apitz-Castro R, Gil F, Aguirre T, Piras MM, Piras R: Inhibition of phosphatidylcholine biosynthesis and cell proliferation in Trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. Biochem Pharmacol. 1993 Jun 22;45(12):2381-7.
4. Kaschula CH, Hunter R, Parker MI: Garlic-derived anticancer agents: structure and biological activity of ajoene. Biofactors. 2010 Jan-Feb;36(1):78-85. doi: 10.1002/biof.76.
5. Srivastava KC, Tyagi OD: Effects of a garlic-derived principle (ajoene) on aggregation and arachidonic acid metabolism in human blood platelets. Prostaglandins Leukot Essent Fatty Acids. 1993 Aug;49(2):587-95.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.