Record Information
Version1.0
Creation date2010-04-08 22:09:45 UTC
Update date2018-05-28 22:52:10 UTC
Primary IDFDB011636
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAjoene
DescriptionIsolated from garlic (Allium sativum) extracts. Nutriceutical with anti-cancer props. Ajoene (pronounced /???ho?i?n/) 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).
CAS Number92285-01-3
Structure
Thumb
Synonyms
SynonymSource
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
2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9CIdb_source
Ajoene, trans-biospider
Trans-ajoenebiospider
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 RuleYesChemAxon
Chemical FormulaC9H14OS3
IUPAC name3-{[(1Z)-3-(prop-2-ene-1-sulfinyl)prop-1-en-1-yl]disulfanyl}prop-1-ene
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
Isomeric SMILESC=CCSS\C=C/CS(=O)CC=C
Average Molecular Weight234.402
Monoisotopic Molecular Weight234.02067714
Classification
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 46.12%; H 6.02%; O 6.83%; S 41.04%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[neutral] lmax 240 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-38a71ef9ab244c72057dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000l-7890000000-11928f7c30159af165e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9600000000-c607fc1496412765e8c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-a2836ecdf1469af5047cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0016-6960000000-e17a4526d3baecc4e388View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-9300000000-d62719e8491d22e01b5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f72-9300000000-e0cce5cae13d413bf294View in MoNA
ChemSpider ID8056824
ChEMBL IDNot Available
KEGG Compound IDC16757
Pubchem Compound ID9881148
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33566
CRC / DFC (Dictionary of Food Compounds) IDGWS23-E:GWS23-E
EAFUS IDNot Available
Dr. Duke IDTRANS-AJOENE|TRANS-CIS-AJOENE|AJOENE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAjoene
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
anti allergic50857 A drug used to treat allergic reactions.DUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
anti HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti leukotriene35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti lymphomicDUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti metastatic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti mutagenicDUKE
anti mycoticDUKE
anti plateletDUKE
anti proliferantDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti stomatiticDUKE
anti thrombotic50248 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.DUKE
anti trypanosomic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
apoptoticDUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
candidicideDUKE
candidistatDUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
cytostaticDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
fungistatDUKE
Gram(+)icide33282 A substance that kills or slows the growth of bacteria.DUKE
Gram(-)icide33282 A substance that kills or slows the growth of bacteria.DUKE
hypocholesterolemicDUKE
lipolyticDUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
NF-kappa-B inducerDUKE
nitric-oxide inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
prostaglandin inhibitor49023 A compound that inhibits the action of prostaglandins.DUKE
prostaglandin-synthetase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
protisticideDUKE
tineacide52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
trypanocideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).