squamocin

2(5H)-furanone, 3-(13-(5'-(1,5-dimethylundecyl)octahydro(2,2'-bifuran)-5-yl)-13-hydroxytridecyl)-5-methyl-

CAS: 120298-30-8 C39 H70 O5 MW: 618.98290000

Identification

Namesquamocin
IUPAC(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
CAS Number120298-30-8
FDA UNIISearch
Molecular FormulaC39 H70 O5
Molecular Weight618.98290000
Nikkaji NumberJ458.692A

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 7.216e-006 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for squamocin usage levels up tonot for fragrance use.
Recommendation for squamocin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

apple custard apple apple custard apple cherimoya uvaria narum

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 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).