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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 |
| Soluble in: |
| | water, 7.216e-006 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: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for bullatacin usage levels up to: | | | not for fragrance use.
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| Recommendation for bullatacin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :11124994 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one |
| Chemidplus:0123123320 |
References:
| | (2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 11124994 |
| Pubchem (cas): | 123123-32-0 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | annonareticin | | (2S)-4-[(2R,13R)-2,13- | dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one | | 2(5H)- | furanone, 3-(2,13-dihydroxy-13-(octahydro-5'-(1-hydroxyundecyl)(2,2'-bifuran)-5-yl)tridecyl)-5-methyl-, (2R-(2alpha(2'R*,5'R*(S*)),5beta(1(S*),2R*,13R*)))- | | | rolliniastatin 2 | | | squamocin G |
Articles:
| PubMed:The fruit of Annona squamosa L. as a source of environmental neurotoxins: From quantification of squamocin to annotation of Annonaceous acetogenins by LC-MS/MS analysis. |
| PubMed:[Structure activity relationship of annonaceous acetogenins against multidrug resistant human lung cancer cell line A549/Taxol in vitro]. |
| PubMed:Reduction of Synthetic Ubiquinone QT Catalyzed by Bovine Mitochondrial Complex I Is Decoupled from Proton Translocation. |
| PubMed:Acetogenins as Potential Anticancer Agents. |
| PubMed:Amilorides bind to the quinone binding pocket of bovine mitochondrial complex I. |
| PubMed:Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry. |
| PubMed:Site-specific chemical labeling of mitochondrial respiratory complex I through ligand-directed tosylate chemistry. |
| PubMed:Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. |
| PubMed:Antitumor activity and toxicity relationship of annonaceous acetogenins. |
| PubMed:Anti-tumor activity of Annona squamosa seeds extract containing annonaceous acetogenin compounds. |
| PubMed:Determination of bullatacin in rat plasma by liquid chromatography-mass spectrometry. |
| PubMed:Forskolin and derivatives as tools for studying the role of cAMP. |
| PubMed:Cytotoxic bistetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa. |
| PubMed:Bis-THF motif of acetogenin binds to the third matrix-side loop of ND1 subunit in mitochondrial NADH-ubiquinone oxidoreductase. |
| PubMed:In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis: trematocidal plant alcoholic extracts. |
| PubMed:The membrane subunit NuoL(ND5) is involved in the indirect proton pumping mechanism of Escherichia coli complex I. |
| PubMed:Susceptibility of complete bacteria and spheroplasts of Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi to rolliniastatin-2. |
| PubMed:Exploring the binding site of delta(lac)-acetogenin in bovine heart mitochondrial NADH-ubiquinone oxidoreductase. |
| PubMed:The ND2 subunit is labeled by a photoaffinity analogue of asimicin, a potent complex I inhibitor. |
| PubMed:Identification of annonaceous acetogenins in the ripe fruit of the North American pawpaw ( Asimina triloba ). |
| PubMed:Bullatacin triggered ABCB1-overexpressing cell apoptosis via the mitochondrial-dependent pathway. |
| PubMed:Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species. |
| PubMed:Two new adjacent bis-tetrahydrofuran annonaceous acetogenins from seeds of Annona cornifolia. |
| PubMed:Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity. |
| PubMed:Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I. |
| PubMed:Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin. |
| PubMed:An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue. |
| PubMed:Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I. |
| PubMed:Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane. |
| PubMed:Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes. |
| PubMed:Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin. |
| PubMed:Synthesis and inhibition mechanism of Delta lac-acetogenins, a novel type of inhibitor of bovine heart mitochondrial complex I. |
| PubMed:Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I. |
| PubMed:In vitro antitumor SAR of threo/cis/threo/cis/erythro bis-THF acetogenins: correlations with their inhibition of mitochondrial Complex I. |
| PubMed:New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata. |
| PubMed:A modular synthesis of annonaceous acetogenins. |
| PubMed:[Inhibition of oxygen consumption by annonaceous acetogenins in liver cell respiration and their structure-activity relationship]. |
| PubMed:Selective action of acetogenin mitochondrial complex I inhibitors. |
| PubMed:Bullatacin, a potent antitumor Annonaceous acetogenin, induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells. |
| PubMed:[Antitumor effect of anuoning]. |
| PubMed:[Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins]. |
| PubMed:Mimicry of annonaceous acetogenins: enantioselective synthesis of a (4R)-hydroxy analogue having potent antitumor activity. |
| PubMed:Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction. |
| PubMed:Gamma-lactone-Functionalized antitumoral acetogenins are the most potent inhibitors of mitochondrial complex I. |
| PubMed:Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I. |
| PubMed:Total synthesis of asimicin and bullatacin. |
| PubMed:Circumvention of tumor multidrug resistance by a new annonaceous acetogenin: atemoyacin-B. |
| PubMed:Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics. |
| PubMed:New annonaceous acetogenins from Rollinia mucosa. |
| PubMed:Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa. |
| PubMed:Kinetic characterization of mitochondrial complex I inhibitors using annonaceous acetogenins. |
| PubMed:Inhibition of mitochondrial oxidative phosphorylation induces hyper-expression of glutamic acid decarboxylase in pancreatic islet cells. |
| PubMed:NADH-quinone oxidoreductase: PSST subunit couples electron transfer from iron-sulfur cluster N2 to quinone. |
| PubMed:Biochemical features of mtDNA 14484 (ND6/M64V) point mutation associated with Leber's hereditary optic neuropathy. |
| PubMed:Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase). |
| PubMed:Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae). |
| PubMed:Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea. |
| PubMed:Acetogenins from seeds of Annona reticulata. |
| PubMed:Membrane conformations and their relation to cytotoxicity of asimicin and its analogues. |
| PubMed:Cherimolin-1, new selective inhibitor of the first energy-coupling site of the NADH: ubiquinone oxidoreductase (complex I). |
| PubMed:Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent. |
| PubMed:Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells. |
| PubMed:Leber's hereditary optic neuropathy: biochemical effect of 11778/ND4 and 3460/ND1 mutations and correlation with the mitochondrial genotype. |
| PubMed:The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells. |
| PubMed:Measurement of the membrane potential generated by complex I in submitochondrial particles. |
| PubMed:Genetic evidence for the existence of two quinone related inhibitor binding sites in NADH-CoQ reductase. |
| PubMed:Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins. |
| PubMed:Squamotacin: an annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3). |
| PubMed:SARs of annonaceous acetogenins in rat liver mitochondria. |
| PubMed:The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba. |
| PubMed:Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes. |
| PubMed:Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I). |
| PubMed:Asimin, asiminacin, and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba. |
| PubMed:Bullatacin--in vivo and in vitro experience in an ovarian cancer model. |
| PubMed:Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin. |
| PubMed:Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba. |
| PubMed:Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa. |
| PubMed:Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata. |
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