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

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Name:(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 Number: 120298-30-8Picture of molecule3D/inchi
Other(deleted CASRN):129214-51-3
FDA UNII: Search
Nikkaji Web:J458.692A
XlogP3-AA:9.50 (est)
Molecular Weight:618.98290000
Formula:C39 H70 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
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:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Squamocin 95%
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for squamocin usage levels up to:
 not for fragrance use.
 
Recommendation for squamocin flavor usage levels up to:
 not for flavor use.
 
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:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08545
HMDB (The Human Metabolome Database):Search
FooDB:FDB018779
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 apple custard apple
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 apple custard apple
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 cherimoya
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 uvaria narum
Search Trop Picture
 
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).
 
Notes:
from seeds of annona squamosa; a trihydroxy-bis-tetrahydrofuran fatty acid lactone; inhibits e. coli nadh:quinone oxidoreductase (ndh-1). Constit. of various Annona spp.
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