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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, 7.712e-005 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
| BOC Sciences |
| For experimental / research use only. |
| Annonacin >97%
Odor: characteristic Use: Annonacin is a natural lipophilic mitochondrial complex I inhibitor found in the herbs of Annona glabra. Annonacin has cytotoxicity and may have anti-cancer activity.
anti-cancer |
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 annonacin usage levels up to: | | | not for fragrance use.
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| Recommendation for annonacin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
| EPI System: | View |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 354398 |
| National Institute of Allergy and Infectious Diseases: | Data |
| | (2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one |
| Chemidplus: | 0111035655 |
References:
| | (2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 354398 |
| Pubchem (cas): | 111035-65-5 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (2S)-2- | methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one |
Articles:
| PubMed: | Annonacin Exerts Antitumor Activity through Induction of Apoptosis and Extracellular Signal-regulated Kinase Inhibition. |
| PubMed: | Characterization of interactions of eggPC lipid structures with different biomolecules. |
| PubMed: | Acetogenins and alkaloids during the initial development of Annona muricata L. (Annonaceae). |
| PubMed: | Annona muricata leaves extracts prevent DMBA/TPA-induced skin tumorigenesis via modulating antioxidants enzymes system in ICR mice. |
| PubMed: | Structural Characterisation of Acetogenins from Annona muricata by Supercritical Fluid Chromatography Coupled to High-Resolution Tandem Mass Spectrometry. |
| PubMed: | The Value of Caspase-3 after the Application ofAnnona muricataLeaf Extract in COLO-205 Colorectal Cancer Cell Line. |
| 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: | PERK activation mitigates tau pathologyin vitroandin vivo. |
| PubMed: | Chronic consumption of Annona muricata juice triggers and aggravates cerebral tau phosphorylation in wild-type and MAPT transgenic mice. |
| PubMed: | Validation data for the quantification of the Annonaceous acetogenin annonacin in Rat brain by UPLC-MS/MS. |
| PubMed: | Quantification of the environmental neurotoxin annonacin in Rat brain by UPLC-MS/MS. |
| PubMed: | Method development for quantification of the environmental neurotoxin annonacin in Rat plasma by UPLC-MS/MS and application to a pharmacokinetic study. |
| PubMed: | Acetogenins as Potential Anticancer Agents. |
| PubMed: | Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS. |
| PubMed: | Mitochondrial complex 1 inhibition increases 4-repeat isoform tau by SRSF2 upregulation. |
| PubMed: | Styryllactones and acetogenins from the fruits of Goniothalamus macrocalyx. |
| PubMed: | Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice. |
| PubMed: | Natural toxins implicated in the development of Parkinson's disease. |
| PubMed: | Annonacin in Asimina triloba fruit: implication for neurotoxicity. |
| PubMed: | Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells. |
| PubMed: | Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23). |
| PubMed: | Synthesis of annonacin isolated from Annona densicoma. |
| PubMed: | The alternative medicine pawpaw and its acetogenin constituents suppress tumor angiogenesis via the HIF-1/VEGF pathway. |
| PubMed: | Complex I: inhibitors, inhibition and neurodegeneration. |
| PubMed: | Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies. |
| PubMed: | Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I. |
| PubMed: | Atypical parkinsonism in the Caribbean island of Guadeloupe: etiological role of the mitochondrial complex I inhibitor annonacin. |
| PubMed: | Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons. |
| PubMed: | Atypical parkinsonism in Guadeloupe: a common risk factor for two closely related phenotypes? |
| PubMed: | Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae? |
| PubMed: | Acetogenins in Annona muricata L. (annonaceae) leaves are potent molluscicides. |
| PubMed: | Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe. |
| PubMed: | Montacin and cis-montacin, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona montana. |
| PubMed: | In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I. |
| PubMed: | Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe. |
| PubMed: | Inhibitory effects on mitochondrial complex I of semisynthetic mono-tetrahydrofuran acetogenin derivatives. |
| PubMed: | The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism. |
| PubMed: | Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. |
| PubMed: | Selective action of acetogenin mitochondrial complex I inhibitors. |
| PubMed: | [Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins]. |
| PubMed: | New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata. |
| PubMed: | Cytotoxic compounds from Annonaceus species as DNA topoisomerase I poisons. |
| PubMed: | Annonaceous acetogenins from the leaves of Annona montana. |
| PubMed: | Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana. |
| PubMed: | Murihexol, a linear acetogenin from Annona muricata. |
| PubMed: | Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds. |
| PubMed: | Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates. |
| PubMed: | Three novel monotetrahydrofuran annonaceous acetogenins from Annona montana. |
| PubMed: | Insecticidal and mutagenic evaluation of two annonaceous acetogenins. |
| PubMed: | The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins. |
| PubMed: | Cytotoxicity and antileishmanial activity of Annona muricata pericarp. |
| PubMed: | cis-Annonacin and (2,4)-cis-and trans-isoannonacins: cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds of Annona cherimolia. |
| PubMed: | Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba. |
| PubMed: | A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii. |
| PubMed: | The localisations in liposomal membranes of the tetrahydrofuran ring moieties of the annonaceous acetogenins, annonacin and sylvaticin, as determined by 1H NMR spectroscopy. |
| PubMed: | Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea. |
| PubMed: | In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins. |
| PubMed: | [Studies on the chemical constituents of Annona muricata]. |
| PubMed: | Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba. |
| PubMed: | Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata. |
| PubMed: | Determination of structure-activity relationships of Annonaceous acetogenins by inhibition of oxygen uptake in rat liver mitochondria. |
| PubMed: | Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata. |
| PubMed: | Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia. |
| PubMed: | Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata. |
| PubMed: | Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata. |
| PubMed: | Bioactive annonaceous acetogenins from the bark of Xylopia aromatica. |
| PubMed: | Biologically active acetogenins from stem bark of Asimina triloba. |
| PubMed: | [Annomonysvin: a new cytotoxic gamma-lactone-monotetrahydrofuranyl acetogenin from Annona montana]. |
| PubMed: | [Annonacins and Annonastatin from Annona squamosa]. |
| PubMed: | Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae). |
| PubMed: | Annonacin, a novel, biologically active polyketide from Annona densicoma. |
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