Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
Assay: | 95.00 to 100.00
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Food Chemicals Codex Listed: | No |
Boiling Point: | 376.05 °C. @ 760.00 mm Hg (est)
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Flash Point: | 358.00 °F. TCC ( 181.20 °C. ) (est)
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logP (o/w): | 2.536 (est) |
Soluble in: |
| water, 327.2 mg/L @ 25 °C (est) |
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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Hazards identification |
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Classification of the substance or mixture |
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
None found. |
GHS Label elements, including precautionary statements |
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Pictogram | |
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Hazard statement(s) |
None found. |
Precautionary statement(s) |
None found. |
Oral/Parenteral Toxicity: |
Not determined
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Dermal Toxicity: |
Not determined
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Inhalation Toxicity: |
Not determined
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Safety in Use Information:
Category: | natural substances and extractives |
Recommendation for ajoene usage levels up to: | | not for fragrance use.
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Recommendation for ajoene flavor usage levels up to: |
| not for flavor use.
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Safety References:
References:
| 1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene |
NIST Chemistry WebBook: | Search Inchi |
Pubchem (cid): | 72373 |
Pubchem (sid): | 135029901 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
1-( | allyldisulfanyl)-3-(allylsulfinyl)-1-propene | | disulfide, 2-propenyl 3-(2-propenylsulfinyl)-1-propenyl
| 1-( | prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene | 4,5,9- | trithiadodeca-1,6,11-triene 9-oxide |
Articles:
PubMed:Development of garlic bioactive compounds analytical methodology based on liquid phase microextraction using response surface design. Implications for dual analysis: Cooked and biological fluids samples. |
PubMed:The Immunomodulatory Potential of Selected Bioactive Plant-Based Compounds in Breast Cancer: A Review. |
PubMed:The synthetic ajoene analog SPA3015 induces apoptotic cell death through crosstalk between NF-κB and PPARγ in multidrug-resistant cancer cells. |
PubMed:Chemical composition and bioactive compounds of garlic (Allium sativum L.) as affected by pre- and post-harvest conditions: A review. |
PubMed:The redox-active drug metronidazole and thiol-depleting garlic compounds act synergistically in the protist parasite Spironucleus vortens. |
PubMed:Exploiting the antivirulence efficacy of an ajoene-ciprofloxacin combination against Pseudomonas aeruginosa biofilm associated murine acute pyelonephritis. |
PubMed:Antileishmanial and Immunomodulatory Activity of Allium sativum (Garlic): A Review. |
PubMed:Natural compounds for pediatric cancer treatment. |
PubMed:ROS-mediated activation of JNK/p38 contributes partially to the pro-apoptotic effect of ajoene on cells of lung adenocarcinoma. |
PubMed:The garlic compound ajoene targets protein folding in the endoplasmic reticulum of cancer cells. |
PubMed:Virtual Screening of Natural and Synthetic Ligands Against Diabetic Retinopathy by Molecular Interaction With Angiopoietin-2. |
PubMed:Optimizing conditions for E-and Z-ajoene formation from garlic juice using response surface methodology. |
PubMed:Applications of thin-layer chromatography in extraction and characterisation of ajoene from garlic bulbs. |
PubMed:Antioxidant defences of Spironucleus vortens: Glutathione is the major non-protein thiol. |
PubMed:Systemic approaches identify a garlic-derived chemical, Z-ajoene, as a glioblastoma multiforme cancer stem cell-specific targeting agent. |
PubMed:Antimycobacterial and Antibacterial Activity of Allium sativum Bulbs. |
PubMed:Neuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia. |
PubMed:Solid phase microextraction coupled to liquid chromatography. Analysis of organosulphur compounds avoiding artifacts formation. |
PubMed:Investigating the responses of Cronobacter sakazakii to garlic-drived organosulfur compounds: a systematic study of pathogenic-bacterium injury by use of high-throughput whole-transcriptome sequencing and confocal micro-raman spectroscopy. |
PubMed:Enhancement of intestinal IgA production by Ajoene in mice. |
PubMed:Application of the DataChip/MetaChip technology for the evaluation of ajoene toxicity in vitro. |
PubMed:Molecular mechanisms for the anti-cancer effects of diallyl disulfide. |
PubMed:A rethinking on the benefits and drawbacks of common antioxidants and a proposal to look for the antioxidants in allium products as ideal agents: a review. |
PubMed:Garlic as an anti-diabetic agent: recent progress and patent reviews. |
PubMed:Anti-inflammatory activity of sulfur-containing compounds from garlic. |
PubMed:Disrupted intracellular redox balance of the diplomonad fish parasite Spironucleus vortens by 5-nitroimidazoles and garlic-derived compounds. |
PubMed:Transformation of synthetic allicin: the influence of ultrasound, microwaves, different solvents and temperatures, and the products isolation. |
PubMed:[In vitro synergisms among hydrazones, ajoeno and posaconazole against Cryptococcus spp]. |
PubMed:A comprehensive review of vaginitis phytotherapy. |
PubMed:Structure-activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells. |
PubMed:Ajoene, a sulfur-rich molecule from garlic, inhibits genes controlled by quorum sensing. |
PubMed:Synergistic antibacterial efficacy of early combination treatment with tobramycin and quorum-sensing inhibitors against Pseudomonas aeruginosa in an intraperitoneal foreign-body infection mouse model. |
PubMed:[In vitro antifungal activity of ajoene on five clinical isolates of Histoplasma capsulatum var. capsulatum]. |
PubMed:Potential beneficial effects of garlic in oncohematology. |
PubMed:Anti-proliferation activity of synthetic ajoene analogues on cancer cell-lines. |
PubMed:Effect of garlic and allium-derived products on the growth and metabolism of Spironucleus vortens. |
PubMed:Antithrombotic effects of naturally derived products on coagulation and platelet function. |
PubMed:Ajoene, a stable garlic by-product, inhibits high fat diet-induced hepatic steatosis and oxidative injury through LKB1-dependent AMPK activation. |
PubMed:Ajoene, a stable garlic by-product, has an antioxidant effect through Nrf2-mediated glutamate-cysteine ligase induction in HepG2 cells and primary hepatocytes. |
PubMed:Garlic-derived anticancer agents: structure and biological activity of ajoene. |
PubMed:Garlic derivatives (PTS and PTS-O) differently affect the ecology of swine faecal microbiota in vitro. |
PubMed:Enhanced activation of the transient receptor potential channel TRPA1 by ajoene, an allicin derivative. |
PubMed:[In vitro inhibitory effect of ajoene on Candida isolates recovered from vaginal discharges]. |
PubMed:Potentiated cytotoxic effects of statins and ajoene in murine melanoma cells. |
PubMed:Ajoene exerts potent effects in 3T3-L1 adipocytes by inhibiting adipogenesis and inducing apoptosis. |
PubMed:Thermostability of allicin determined by chemical and biological assays. |
PubMed:Antifungal activity of ajoene on experimental murine paracoccidioidomycosis. |
PubMed:[Synergy between ajoene and ketoconazole in isolates of Microsporum canis. A preliminary study using fractional inhibitory concentration technique (FIC)]. |
PubMed:Substituted ajoenes as novel anti-cancer agents. |
PubMed:Multitargeted prevention and therapy of cancer by diallyl trisulfide and related Allium vegetable-derived organosulfur compounds. |
PubMed:Phytochemicals and regulation of the adipocyte life cycle. |
PubMed:[Activity of ajoene on dermatophytes, Candida albicans and Malassezia furfur.]. |
PubMed:Experimental paracoccidioidomycosis: alternative therapy with ajoene, compound from Allium sativum, associated with sulfamethoxazole/trimethoprim. |
PubMed:Activities of Z-ajoene against tumour and viral spreading in vitro. |
PubMed:[Characteristics of uptake, transport and efflux of Z- and E-ajoenes in Caco-2 cell monolayers in vitro]. |
PubMed:Enhancement of ajoene-induced apoptosis by conjugated linoleic acid in 3T3-L1 adipocytes. |
PubMed:Virucidal agents in the eve of manorapid synergy. |
PubMed:Chromoblastomycosis in children and adolescents in the endemic area of the Falcón State, Venezuela. |
PubMed:[Ajoene the main active compound of garlic (Allium sativum): a new antifungal agent]. |
PubMed:Molecular mechanisms of apoptosis induced by ajoene in 3T3-L1 adipocytes. |
PubMed:Prophylactic effects of ajoene on cerebral injury in stroke-prone spontaneously hypertensive rats (SHRSP). |
PubMed:[Z-ajoene causes cell cycle arrest at G2/M and decrease of telomerase activity in HL-60 cells]. |
PubMed:Antidiabetic effects of ajoene in genetically diabetic KK-A(y) mice. |
PubMed:Ajoene inhibits both primary tumor growth and metastasis of B16/BL6 melanoma cells in C57BL/6 mice. |
PubMed:Paracoccidioides brasiliensis, paracoccidioidomycosis, and antifungal antibiotics. |
PubMed:Novel treatments for obesity and osteoporosis: targeting apoptotic pathways in adipocytes. |
PubMed:Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents. |
PubMed:[An ELISA test for the study of the therapeutic evolution of chromoblastomycosis by Cladophialophora carrionii in the endemic area of Falcon State, Venezuela]. |
PubMed:Allicin and allicin-derived garlic compounds increase breath acetone through allyl methyl sulfide: use in measuring allicin bioavailability. |
PubMed:Beneficial effects of a polar fraction of garlic (Allium sativum Linn) oil in rats fed with two different high fat diets. |
PubMed:Suppression of the nuclear factor-kappaB activation pathway by spice-derived phytochemicals: reasoning for seasoning. |
PubMed:Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice. |
PubMed:Ajoene (natural garlic compound): a new anti-leukaemia agent for AML therapy. |
PubMed:Effect of ajoene, a natural antitumor small molecule, on human 20S proteasome activity in vitro and in human leukemic HL60 cells. |
PubMed:Apoptotic and anti-adhesion effect of ajoene, a garlic derived compound, on the murine melanoma B16F10 cells: possible role of caspase-3 and the alpha(4)beta(1) integrin. |
PubMed:Ajoene and 5-fluorouracil in the topical treatment of Cladophialophora carrionii chromoblastomycosis in humans: a comparative open study. |
PubMed:Inhibition of baboon platelet aggregation in vitro and in vivo by the garlic derivative, ajoene. |
PubMed:Ajoene inhibits the activation of human endothelial cells induced by porcine cells: implications for xenotransplantation. |
PubMed:The garlic-derived organosulfur component ajoene decreases basal cell carcinoma tumor size by inducing apoptosis. |
PubMed:Ajoene, a garlic compound, inhibits protein prenylation and arterial smooth muscle cell proliferation. |
PubMed:The in vitro susceptibility of Scedosporium prolificans to ajoene, allitridium and a raw extract of garlic (Allium sativum). |
PubMed:Ajoene-induced cell death in human promyeloleukemic cells does not require JNK but is amplified by the inhibition of ERK. |
PubMed:Inhibition by ajoene of skin-tumor promotion in mice. |
PubMed:Z-ajoene induces apoptosis of HL-60 cells: involvement of Bcl-2 cleavage. |
PubMed:Antiproliferative and leishmanicidal effect of ajoene on various Leishmania species: ultrastructural study. |
PubMed:Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties. |
PubMed:Ajoene, a garlic-derived natural compound, enhances chemotherapy-induced apoptosis in human myeloid leukaemia CD34-positive resistant cells. |
PubMed:Ajoene, an experimental anti-leukemic drug: mechanism of cell death. |
PubMed:Protective effect of ajoene on acetaminophen-induced hepatic injury in mice. |
PubMed:Garlic extract for HIV? |
PubMed:Ajoene, a natural product with non-steroidal anti-inflammatory drug (NSAID)-like properties? |
PubMed:Thermochemical transformation of sulfur compounds in Japanese domestic Allium, Allium victorialis L. |
PubMed:Efficacy of ajoene in the treatment of tinea pedis: a double-blind and comparative study with terbinafine. |
PubMed:Structure-activity relationships for selected sulfur-rich antithrombotic compounds. |
PubMed:Ajoene in the topical short-term treatment of tinea cruris and tinea corporis in humans. Randomized comparative study with terbinafine. |
PubMed:An organosulfur compound isolated from oil-macerated garlic extract, and its antimicrobial effect. |
PubMed:Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies. |
PubMed:Tityus discrepans venom produces a respiratory distress syndrome in rabbits through an indirect mechanism. |
PubMed:Ajoene [(e,z)-4,5,9-trithiadodeca-1,6,11-triene 9 oxide] does not exhibit antiviral activity at subtoxic concentrations. |
PubMed:Selective in vitro protection of SIVagm-induced cytolysis by ajoene, [(E)-(Z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]. |
PubMed:Effect of allicin and ajoene, two compounds of garlic, on inducible nitric oxide synthase. |
PubMed:Antimicrobial activity of a compound isolated from an oil-macerated garlic extract. |
PubMed:Ajoene, a compound of garlic, induces apoptosis in human promyeloleukemic cells, accompanied by generation of reactive oxygen species and activation of nuclear factor kappaB. |
PubMed:[Effect of the garlic tablets allicor on thrombocyte aggregation in vitro and ex vivo]. |
PubMed:Inhibition of Paracoccidioides brasiliensis by ajoene is associated with blockade of phosphatidylcholine biosynthesis. |
PubMed:Inhibition by ajoene of protein tyrosine phosphatase activity in human platelets. |
PubMed:Effects of Ajoene on lymphocyte and macrophage membrane-dependent functions. |
PubMed:In vitro suppression of HIV-1 replication by ajoene [(e)-(z)-4,5,9-trithiadodeca-1,6,11-triene-9 oxide]. |
PubMed:Lipid biosynthesis pathways as chemotherapeutic targets in kinetoplastid parasites. |
PubMed:Antimutagenic effects of ajoene, an organosulfur compound derived from garlic. |
PubMed:Inhibition of microbial growth by ajoene, a sulfur-containing compound derived from garlic. |
PubMed:Efficacy of ajoene, an organosulphur derived from garlic, in the short-term therapy of tinea pedis. |
PubMed:Therapeutic actions of garlic constituents. |
PubMed:Synergistic effects of ajoene and the microwave power density memories of water on germination inhibition of fungal spores. |
PubMed:A garlic derivative, ajoene, inhibits platelet deposition on severely damaged vessel wall in an in vivo porcine experimental model. |
PubMed:Inhibition of cholesterol biosynthesis by allicin and ajoene in rat hepatocytes and HepG2 cells. |
PubMed:In vivo activity of ajoene against rodent malaria. |
PubMed:Injuries to cultivated BJA-B cells by ajoene, a garlic-derived natural compound: cell viability, glutathione metabolism, and pools of acidic amino acids. |
PubMed:Effects of a garlic-derived principle (ajoene) on aggregation and arachidonic acid metabolism in human blood platelets. |
PubMed:Inhibition of phosphatidylcholine biosynthesis and cell proliferation in Trypanosoma cruzi by ajoene, an antiplatelet compound isolated from garlic. |
PubMed:Effect of ajoene on dimorphism of Paracoccidioides brasiliensis. |
PubMed:Effect of ajoene, the major antiplatelet compound from garlic, on platelet thrombus formation. |
PubMed:In vitro virucidal effects of Allium sativum (garlic) extract and compounds. |
PubMed:Ajoene antagonizes integrin-dependent processes in HIV-infected T-lymphoblasts. |
PubMed:Kinetics of merthiolate-induced aggregation of human platelets. |
PubMed:Wine and coronary heart disease. |
PubMed:Functional implications of tyrosine protein phosphorylation in platelets. Simultaneous studies with different agonists and inhibitors. |
PubMed:Inhibition of cholesterol synthesis in vitro by extracts and isolated compounds prepared from garlic and wild garlic. |
PubMed:[Kinetics of merthiolate-induced aggregation of human platelets]. |
PubMed:Inhibition of whole blood platelet-aggregation by compounds in garlic clove extracts and commercial garlic products. |
PubMed:Potassium channel activation in vascular smooth muscle. |
PubMed:[The ajoene blockade of integrin-dependent processes in an HIV-infected cell system]. |
PubMed:Binding of aflatoxin B1 to DNA inhibited by ajoene and diallyl sulfide. |
PubMed:Evidence for direct coupling of primary agonist-receptor interaction to the exposure of functional IIb-IIIa complexes in human blood platelets. Results from studies with the antiplatelet compound ajoene. |
PubMed:Isolation and Identification of Homologues of Ajoene and Alliin from Bulb-Extracts of Allium ursinum. |
PubMed:[Formation of allicin from dried garlic (Allium sativum): a simple HPTLC method for simultaneous determination of allicin and ajoene in dried garlic and garlic preparations]. |
PubMed:Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products. |
PubMed:Influence of thiols and inhibitors of prostaglandin biosynthesis on the carcinogen-induced development of mammary lesions in vitro. |
PubMed:The role of adhesive interactions and extracellular matrix fibronectin from human polymorphonuclear leukocytes in the respiratory burst. |
PubMed:Organosulfur compounds of garlic modulate mutagenesis, metabolism, and DNA binding of aflatoxin B1. |
PubMed:Potassium channel activation, hyperpolarization, and vascular relaxation. |
PubMed:The cytotoxic effect of ajoene, a natural product from garlic, investigated with different cell lines. |
PubMed:Products of Allicin Transformation: Ajoenes and Dithiins, Characterization and their Determination by HPLC*. |
PubMed:[Adhesion receptors--regulators of respiratory burst in neutrophils]. |
PubMed:Ajoene prevents fat digestion by human gastric lipase in vitro. |
PubMed:Inhibition of growth of the dimorphic fungus Paracoccidioides brasiliensis by ajoene. |
PubMed:Ajoene, the antiplatelet compound derived from garlic, specifically inhibits platelet release reaction by affecting the plasma membrane internal microviscosity. |
PubMed:Interaction of antiaggregant molecule ajoene with membranes. An ESR and 1H, 2H, 31P-NMR study. |
PubMed:Inhibition of soybean lipoxygenase and mouse skin tumor promotion by onion and garlic components. |
PubMed:Reversible prevention of platelet activation by (E,Z)-4,5,9-trithiadodeca-1,6,11-triene 9-oxide (ajoene) in dogs under extracorporeal circulation. |
PubMed:Ajoene inhibition of platelet aggregation: possible mediation by a hemoprotein. |
PubMed:Antifungal activity of ajoene derived from garlic. |
PubMed:The molecular basis of the antiplatelet action of ajoene: direct interaction with the fibrinogen receptor. |
PubMed:Ajoene, the antiplatelet principle of garlic, synergistically potentiates the antiaggregatory action of prostacyclin, forskolin, indomethacin and dypiridamole on human platelets. |
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major antiplatelet compound in methanol extract of garlic with other sulfur-containing compounds; also inhibits trypanothione reductase. Isol. 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).
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