1.02010-04-08 22:09:45 UTC2019-11-26 03:05:10 UTCFDB011636AjoeneIsolated 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).2-Propenyl 3-(2-propenylsulfinyl)-1-propenyl disulfide, 9CI2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfide4,5,9-Trithia-1,6,11-dodecatriene 9-oxide4,5,9-Trithiadodeca-1,6,11-triene 9-oxideAjoene, trans-Allyl 3-allylsulfinyl-1-propenyl disulfideDisulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenylTrans-ajoeneC9H14OS3234.402234.020677143-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene92285-01-3C=CCSS\C=C/CS(=O)CC=CInChI=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-IXELFRRANAOWSF-ALCCZGGFSA-N 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).SulfoxidesOrganic compoundsOrganosulfur compoundsSulfoxidesAliphatic acyclic compoundsAllyl sulfur compoundsHydrocarbon derivativesOrganic disulfidesOrganic oxidesSulfenyl compoundsSulfinyl compoundsAliphatic acyclic compoundAllyl sulfur compoundHydrocarbon derivativeOrganic disulfideOrganic oxideOrganic oxygen compoundSulfenyl compoundSulfinyl compoundSulfoxidelogp1.66pka_strongest_acidic14.9pka_strongest_basic-8.1iupac3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-eneaverage_mass234.402mono_mass234.02067714smilesC=CCSS\C=C/CS(=O)CC=CformulaC9H14OS3inchiInChI=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-inchikeyIXELFRRANAOWSF-ALCCZGGFSA-Npolar_surface_area17.07refractivity69polarizability25.3rotatable_bond_count8acceptor_count1donor_count0physiological_charge0formal_charge0HMDB33566#<Reference:0x000055567517b2b0>#<Reference:0x000055567517afb8>#<Reference:0x000055567517ac70>#<Reference:0x000055567517a9c8>#<Reference:0x000055567517a7c0>#<Reference:0x000055567517a4a0>Garden onionType 1specificAllium cepa4679Garden onion (var.)Type 1specificAllium cepa var. cepa4679GarlicType 1specificAllium sativum4682Green onionType 1Onion-family vegetablesUnknowngenericRed onionType 1Soft-necked garlicType 1specificAllium sativum L. var. sativum468226.826.826.8mg/100 gWelsh onionType 1specificAllium fistulosum35875anti aggregant94anti allergic103A drug used to treat allergic reactions.anti bacterial145A substance that kills or slows the growth of bacteria.anti herpetic329A substance that destroys or inhibits replication of viruses.anti HIV333A substance that destroys or inhibits replication of viruses.anti inflammatory370A substance that reduces or suppresses inflammation.anti leukemic393A substance that inhibits or prevents the proliferation of neoplasms.anti leukotriene399A substance that diminishes the rate of a chemical reaction.anti lymphomic414anti malarial416A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti metastatic434A substance that inhibits or prevents the proliferation of neoplasms.anti mutagenic451anti mycotic456anti platelet533anti proliferant547anti prostaglandin550A 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.anti septic603A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti staphylococcic627A substance that kills or slows the growth of bacteria.anti stomatitic630anti thrombotic650Drug that acts on blood and blood-forming organs and those that affect the hemostatic system.anti trypanosomic669A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.anti viral689A substance that destroys or inhibits replication of viruses.antitumor672A substance that inhibits or prevents the proliferation of neoplasms.apoptotic704calcium antagonist748Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.candidicide756candidistat757cyclooxygenase inhibitor849A 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.cyclooxygenase-2 inhibitor841A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.cytostatic858cytotoxic859A role played by the molecular entity or part thereof which causes the development of a pathological process.fungicide940A substance used to destroy fungal pests.fungistat942Gram(-)icide963A substance that kills or slows the growth of bacteria.Gram(+)icide962A substance that kills or slows the growth of bacteria.hypocholesterolemic1016lipolytic1074lipoxygenase inhibitor1077A 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.NF-kappa-B inducer1163nitric-oxide inhibitor1167A substance that diminishes the rate of a chemical reaction.pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.prostaglandin inhibitor1255A compound that inhibits the action of prostaglandins.prostaglandin-synthetase inhibitor1259A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.protisticide1266tineacide1360Any substance introduced into a living organism with therapeutic or diagnostic purpose.trypanocide1384