heptelidic acid
koningic acid
 
Notes:
None found
  • BOC Sciences
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      Product(s):
      57710-57-3 Heptelidic acid ≥95%
      Heptelidic acid is a sesquiterpene lactone produced by the fungus T. koningii displaying antibiotic activity against anaerobic
       
       
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CAS Number: 57710-57-3Picture of molecule3D/inchi
Other(deleted CASRN): 84502-40-9
FDA UNII: 6H8EDV2NKQ
Beilstein Number: 5091359
XlogP3-AA: 1.40 (est)
Molecular Weight: 280.32040000
Formula: C15 H20 O5
NMR Predictor: Predict (works with chrome 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
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
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Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 501.12 °C. @ 760.00 mm Hg (est)
Flash Point: 372.00 °F. TCC ( 189.10 °C. ) (est)
logP (o/w): 2.034 (est)
Soluble in:
 water, 2192 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
BOC Sciences
For experimental / research use only.
Heptelidic acid ≥95%
Odor: characteristic
Use: Heptelidic acid is a sesquiterpene lactone produced by the fungus T. koningii displaying antibiotic activity against anaerobic
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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:
intraperitoneal-mouse LD50  32 mg/kg
Journal of Antibiotics. Vol. 33, Pg. 468, 1980.

oral-mouse LD50  > 100 mg/kg
Japanese Kokai Tokyo Koho Patents. Vol. #82-146793

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for heptelidic acid usage levels up to:
 not for fragrance use.
 
Recommendation for heptelidic acid 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 : 124361
National Institute of Allergy and Infectious Diseases: Data
 (5aS,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
Chemidplus: 0057710573
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References:
 (5aS,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 124361
Pubchem (sid): 135081872
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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
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 avocettin
3,5a,6,7,8,9a-hexahydro-6-isopropyl-1-oxospiro(1H-2-benzoxepin-9,2'-oxirane)-4-carboxylic acid
 koningic acid
(5aS,9S,9aS)-1-oxo-6-propan-2-ylspiro[3,5a,6,7,8,9a-hexahydro-2-benzoxepine-9,2'-oxirane]-4-carboxylic acid
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Articles:
PubMed: Autophagy promotes paclitaxel resistance of cervical cancer cells: involvement of Warburg effect activated hypoxia-induced factor 1-α-mediated signaling.
PubMed: Inhibition of glycolysis attenuates 4-hydroxynonenal-dependent autophagy and exacerbates apoptosis in differentiated SH-SY5Y neuroblastoma cells.
PubMed: Terpenoid and phenolic metabolites from the fungus xylaria sp. associated with termite nests.
PubMed: Glyceraldehyde 3-phosphate dehydrogenase is unlikely to mediate hydrogen peroxide signaling: studies with a novel anti-dimedone sulfenic acid antibody.
PubMed: Novel terpenoids, trichoderonic acids A and B isolated from Trichoderma virens, are selective inhibitors of family X DNA polymerases.
PubMed: Heptelidic acid, a sesquiterpene lactone, inhibits Etoposide-induced apoptosis in human leukemia U937 cells.
PubMed: Glucose-dependent active ATP depletion by koningic acid kills high-glycolytic cells.
PubMed: Mechanism of the stress-induced collapse of the Ran distribution.
PubMed: The glycolytic enzyme glyceraldehyde-3-phosphate dehydrogenase works as an arsenate reductase in human red blood cells and rat liver cytosol.
PubMed: D-Glyceraldehyde causes production of intracellular peroxide in pancreatic islets, oxidative stress, and defective beta cell function via non-mitochondrial pathways.
PubMed: Hydrogen peroxide induces association between glyceraldehyde 3-phosphate dehydrogenase and phospholipase D2 to facilitate phospholipase D2 activation in PC12 cells.
PubMed: Glyceraldehyde-3-phosphate dehydrogenase activity as an independent modifier of methylglyoxal levels in diabetes.
PubMed: A transient brain ischemia- and bacterial endotoxin-induced glial iNOS expression and NO-induced neuronal apoptosis.
PubMed: Heme-dependent radical generation from antimalarial fungal metabolites, radicicol and heptelidic acid.
PubMed: Antimalarial activity of radicicol, heptelidic acid and other fungal metabolites.
PubMed: Koningic acid (a potent glyceraldehyde-3-phosphate dehydrogenase inhibitor)-induced fragmentation and condensation of DNA in NG108-15 cells.
PubMed: Antitumor activity of heptelidic acid chlorohydrin.
PubMed: Inhibition of glyceraldehyde-3-phosphate dehydrogenase by pentalenolactone. 2. Identification of the site of alkylation by tetrahydropentalenolactone.
PubMed: Inhibition of glyceraldehyde-3-phosphate dehydrogenase by phosphorylated epoxides and alpha-enones.
PubMed: A glyceraldehyde-3-phosphate dehydrogenase with eubacterial features in the amitochondriate eukaryote, Trichomonas vaginalis.
PubMed: Glyceraldehyde-3-phosphate dehydrogenase is required for the transport of nitric oxide in platelets.
PubMed: Cloning of two isozymes of Trichoderma koningii glyceraldehyde-3-phosphate dehydrogenase with different sensitivity to koningic acid.
PubMed: Koningic acid (heptelidic acid) inhibition of glyceraldehyde-3-phosphate dehydrogenases from various sources.
PubMed: Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase.
PubMed: Two glyceraldehyde-3-phosphate dehydrogenase isozymes from the koningic acid (heptelidic acid) producer Trichoderma koningii.
PubMed: Inactivation of rabbit muscle glyceraldehyde-3-phosphate dehydrogenase by koningic acid.
PubMed: Specific inhibition of glyceraldehyde-3-phosphate dehydrogenase by koningic acid (heptelidic acid).
PubMed: Structure of heptelidic acid, a new sesquiterpene antibiotic from fungi.
PubMed: A new sesquiterpene antibiotic, heptelidic acid producing organisms, fermentation, isolation and characterization.
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