1.0 2010-04-08 22:09:45 UTC 2019-11-26 03:05:10 UTC FDB011636 Ajoene Isolated 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, 9CI 2-Propenyl-3-(2-propenylsulfinyl)-1-propenyl disulfide 4,5,9-Trithia-1,6,11-dodecatriene 9-oxide 4,5,9-Trithiadodeca-1,6,11-triene 9-oxide Ajoene, trans- Allyl 3-allylsulfinyl-1-propenyl disulfide Disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenyl Trans-ajoene C9H14OS3 234.402 234.02067714 3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene 3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene 92285-01-3 C=CCSS\C=C/CS(=O)CC=C InChI=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). Sulfoxides Organic compounds Organosulfur compounds Sulfoxides Aliphatic acyclic compounds Allyl sulfur compounds Hydrocarbon derivatives Organic disulfides Organic oxides Sulfenyl compounds Sulfinyl compounds Aliphatic acyclic compound Allyl sulfur compound Hydrocarbon derivative Organic disulfide Organic oxide Organic oxygen compound Sulfenyl compound Sulfinyl compound Sulfoxide logp 1.66 ChemAxon pka_strongest_acidic 14.9 ChemAxon pka_strongest_basic -8.1 ChemAxon iupac 3-{[(1Z)-3-[(S)-prop-2-ene-1-sulfinyl]prop-1-en-1-yl]disulfanyl}prop-1-ene ChemAxon average_mass 234.402 ChemAxon mono_mass 234.02067714 ChemAxon smiles C=CCSS\C=C/CS(=O)CC=C ChemAxon formula C9H14OS3 ChemAxon inchi InChI=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- ChemAxon inchikey IXELFRRANAOWSF-ALCCZGGFSA-N ChemAxon polar_surface_area 17.07 ChemAxon refractivity 69 ChemAxon polarizability 25.3 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB33566 #<Reference:0x000055ce319bf190> #<Reference:0x000055ce319befd8> #<Reference:0x000055ce319bee20> #<Reference:0x000055ce319bec68> #<Reference:0x000055ce319beab0> #<Reference:0x000055ce319be8f8> Garden onion Type 1 specific Allium cepa 4679 Garden onion (var.) Type 1 specific Allium cepa var. cepa 4679 Garlic Type 1 specific Allium sativum 4682 Green onion Type 1 Onion-family vegetables Unknown generic Red onion Type 1 Soft-necked garlic Type 1 specific Allium sativum L. var. sativum 4682 26.8 26.8 26.8 mg/100 g Welsh onion Type 1 specific Allium fistulosum 35875 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti HIV 333 A substance that destroys or inhibits replication of viruses. Anti leukemic 393 A substance that inhibits or prevents the proliferation of neoplasms. Anti leukotriene 399 A substance that diminishes the rate of a chemical reaction. Anti metastatic 434 A substance that inhibits or prevents the proliferation of neoplasms. Anti mycotic 456 Anti platelet 533 Anti proliferant 547 Anti prostaglandin 550 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. Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti thrombotic 650 Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. Anti trypanosomic 669 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-aggregant 94 Anti-allergic 103 A drug used to treat allergic reactions. Anti-herpetic 329 A substance that destroys or inhibits replication of viruses. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-lymphomic 414 Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-mutagenic 451 Anti-staphylococcic 627 A substance that kills or slows the growth of bacteria. Anti-stomatitic 630 Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antifungal agent 1360 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Apoptotic 704 Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Candidicide 756 Candidistat 757 Cyclooxygenase inhibitor 849 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. Cyclooxygenase-2 inhibitor 841 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. Cytostatic 858 Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Fungicide 940 A substance used to destroy fungal pests. Fungistat 942 Gram(-)icide 963 A substance that kills or slows the growth of bacteria. Gram(+)icide 962 A substance that kills or slows the growth of bacteria. Hypocholesterolemic 1016 Lipolytic 1074 Lipoxygenase inhibitor 1077 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. NF-kappa-B inducer 1163 Nitric-oxide inhibitor 1167 A substance that diminishes the rate of a chemical reaction. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Prostaglandin inhibitor 1255 A compound that inhibits the action of prostaglandins. Prostaglandin-synthetase inhibitor 1259 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. Protisticide 1266 Trypanocide 1384