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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 squamocin usage levels up to: | | | not for fragrance use.
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| Recommendation for squamocin 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 :441612 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2S)-4-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-13-hydroxytridecyl]-2-methyl-2H-furan-5-one |
| Chemidplus:0120298308 |
References:
| | (2S)-4-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5-dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-13-hydroxytridecyl]-2-methyl-2H-furan-5-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 441612 |
| Pubchem (sid): | 135084052 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | annonin I | | (2S)-4-[(13R)-13-[(2R,5R)-5-[(2R,5R)-5-[(1S,5S)-1,5- | dihydroxyundecyl]oxolan-2-yl]oxolan-2-yl]-13-hydroxytridecyl]-2-methyl-2H-furan-5-one | | 3-(13-(5'-(1,5- | dimethyl undecyl) octahydro(2,2'-bifuran)-5-yl)-13-hydroxytridecyl)-5-methyl-2(5H)-furanone | | 2(5H)- | furanone, 3-(13-(5'-(1,5-dimethylundecyl)octahydro(2,2'-bifuran)-5-yl)-13-hydroxytridecyl)-5-methyl- | | | squamocin A |
Articles:
| Google Patents:Compound iso-squamocin obtained from seeds of annona squamosa and composition containing the same |
| PubMed:Larvicidal and cytotoxic potential of squamocin on the midgut of Aedes aegypti (Diptera: Culicidae). |
| PubMed:Squamocin modulates histone H3 phosphorylation levels and induces G1 phase arrest and apoptosis in cancer cells. |
| PubMed:Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins. |
| PubMed:[The Relative Configuration of Acetogenins Isolated from Annona squamosa: Annonin I (Squamocin) and Annonin VI]. |
| PubMed:Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS. |
| PubMed:Stimulatory effects of squamocin, an Annonaceous acetogenin, on Ca(2+)-activated K+ current in cultured smooth muscle cells of human coronary artery. |
| PubMed:Involvement of caspase-3 activation in squamocin-induced apoptosis in leukemia cell line HL-60. |
| PubMed:Semisynthesis and screening of a small library of pro-apoptotic squamocin analogues: selection and study of a benzoquinone hybrid with an improved biological profile. |
| PubMed:Heterocyclic analogues of squamocin as inhibitors of mitochondrial complex I. On the role of the terminal lactone of annonaceous acetogenins. |
| PubMed:[Mechanism of apoptosis induced by squamocin in leukemia cells]. |
| PubMed:Induction of G2/M phase arrest by squamocin in chronic myeloid leukemia (K562) cells. |
| PubMed:Selective cytotoxicity of squamocin on T24 bladder cancer cells at the S-phase via a Bax-, Bad-, and caspase-3-related pathways. |
| PubMed:Antitumoral effects of squamocin on parental and multidrug resistant MCF7 (human breast adenocarcinoma) cell lines. |
| PubMed:Squamocin-O(1) and squamocin-O(2), new adjacent bis-tetrahydrofuran acetogenins from the seeds of Annona squamosa. |
| PubMed:Semisynthesis of heterocyclic analogues of squamocin, a cytotoxic annonaceous acetogenin, by an unusual oxidative decarboxylation reaction. |
| PubMed:Semisynthesis and biological activity of aminoacyl triesters of squamocin, an annonaceous acetogenin. |
| PubMed:Squamocin and benzyl benzoate, acaricidal components of Uvaria pauci-ovulata bark extracts. |
| PubMed:Highly cytotoxic and neurotoxic acetogenins of the Annonaceae: new putative biological targets of squamocin detected by activity-based protein profiling. |
| PubMed:Biogenetic relationships between Annonaceous acetogenins: squamocin is not a precursor of chamuvarinin based on a semisynthetic study. |
| PubMed:Annonaceous acetogenins: the hydroxyl groups and THF rings are crucial structural elements for targeting the mitochondria, demonstration with the synthesis of fluorescent squamocin analogues. |
| PubMed:Squamocin, a new cytotoxic bis-tetrahydrofuran containing acetogenin from Annona squamosa. |
| PubMed:Squamocin and Rolliniastatin I from the Seeds of Annona reticulata. |
| PubMed:Acetogenins as potential anticancer agents. |
| PubMed:Four cytotoxic annonaceous acetogenins from the seeds of Annona squamosa. |
| PubMed:Nematicidal and antifungal activities of annonaceous acetogenins from Annona squamosa against various plant pathogens. |
| PubMed:Automatic morphological subtyping reveals new roles of caspases in mitochondrial dynamics. |
| PubMed:Insecticidal, mutagenic and genotoxic evaluation of annonaceous acetogenins. |
| PubMed:Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea. |
| PubMed:Quinone-annonaceous acetogenins: synthesis and complex I inhibition studies of a new class of natural product hybrids. |
| PubMed:[Antitumor effect of anuoning]. |
| PubMed:Insecticidal and mutagenic evaluation of two annonaceous acetogenins. |
| PubMed:A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii. |
| PubMed:Antibacterial, antifungal and anthelmintic activities of root barks of Uvaria hookeri and Uvaria narum. |
| PubMed:A spectral graph theoretic approach to quantification and calibration of collective morphological differences in cell images. |
| PubMed:[Chemical constituents from the seeds of Annona squamosa]. |
| PubMed:Callus cultures of Annona squamosa for the production of annonaceous acetogenins. |
| PubMed:Pharmacological roles of the large-conductance calcium-activated potassium channel. |
| PubMed:Remarkable substituent effect: beta-aminosquamocin, a potent dual inhibitor of mitochondrial complexes I and III. |
| PubMed:[Determination of annonaceous acetogenins in annonaceae plants by HPLC]. |
| PubMed:Inhibitory activities of three annonaceous acetogenins on NADH oxidase of chicken liver mitochondria. |
| PubMed:Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy. |
| PubMed:Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I). |
| PubMed:Constituents from Miliusa balansae (Annonaceae). |
| PubMed:Effects of plant lactones on the production of biofilm of Pseudomonas aeruginosa. |
| PubMed:Antimicrobial and cytotoxic constituents from the seeds of Annona squamosa. |
| PubMed:New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata. |
| PubMed:Semisynthesis and cytotoxicity of amino acetogenins and derivatives. |
| PubMed:Aromin-A, an Annonaceous acetogenin from Annona cherimola. |
| PubMed:A new adjacent bis-tetrahydrofuran annonaceous acetogenin from the seeds of Uvaria chamae. |
| PubMed:Chamuvarinin, an acetogenin bearing a tetrahydropyran ring from the roots of Uvaria chamae. |
| 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:Cardiobutanolide, a styryllactone from Goniothalamus cardiopetalus. |
| PubMed:Semisynthesis of antitumoral acetogenins: SAR of functionalized alkyl-chain bis-tetrahydrofuranic acetogenins, specific inhibitors of mitochondrial complex I. |
| PubMed:Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa. |
| PubMed:Recent advances in the fight against leishmaniasis with natural products. |
| PubMed:Acetogenins and other compounds from Rollinia emarginata and their antiprotozoal activities. |
| PubMed:Acetogenins from seeds of Annona reticulata. |
| PubMed:Three new bistetrahydrofuran acetogenins from the seeds of Annona spinescens. |
| PubMed:Bistetrahydrofuranoid acetogenins from Rollinia sericea. |
| PubMed:Biophysical and biochemical studies of bacterial NADH:quinone oxidoreductase (NDH-1). |
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