gossypin
3,5,7,8,3',4'-hexahydroxyflavone-8-glucoside
 
Notes:
do not confuse with gossypin(e) which is synonym for choline.
  • BOC Sciences
    • BOC Sciences
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      Product(s):
      652-78-8 Gossypin
       
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CAS Number: 652-78-8Picture of molecule3D/inchi
FDA UNII: A3Q367XWX9
Nikkaji Web: J94.552H
Beilstein Number: 0071526
MDL: MFCD00017429
Molecular Weight: 480.38000000
Formula: C21 H20 O13
BioActivity Summary: listing
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
Google Patents: Search
US Patents: Search
EU Patents: Search
Pubchem Patents: Search
PubMed: Search
NCBI: Search
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 229.00 to  230.00 °C. @ 760.00 mm Hg
Boiling Point: 886.00 °C. @ 760.00 mm Hg (est)
Flash Point: 591.00 °F. TCC ( 310.80 °C. ) (est)
logP (o/w): -1.320 (est)
Soluble in:
 water, 4.391e+004 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.
Gossypin
Carbosynth
For experimental / research use only.
Gossypin
ExtraSynthese
For experimental / research use only.
Gossypin (HPLC) ≥90%
Sigma-Aldrich: Sigma
For experimental / research use only.
Gossypin ≥90% (HPLC)
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Safety Information:
Preferred SDS: View
 
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:
intravenous-guinea pig LD50  26300 ug/kg
Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 647, 1959.

intraperitoneal-rat LD50  2240 mg/kg
Indian Journal of Pharmacology. Vol. 10, Pg. 277, 1978.

intravenous-rat LD50  125 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 9, Pg. 647, 1959.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for gossypin usage levels up to:
 not for fragrance use.
 
Recommendation for gossypin 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 : 5281621
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Chemidplus: 0000652788
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References:
 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5281621
Pubchem (sid): 135077470
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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
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C10051
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: 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
 hibiscus vitifolious flowers
Search Trop  Picture
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Synonyms:
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
2-(3,4-dihydroxyphenyl)-8-(beta-D-glucopyranosyloxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
2-(3,4-dihydroxyphenyl)-8-(beta-dextro-glucopyranosyl oxy)-3,5,7-trihydroxy-4H-1-benzopyran-4-one
 gossypetin-8-glucoside
3,5,7,8,3',4'-hexahydroxyflavone-8-glucoside
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Articles:
PubMed: Neuroprotective activity of gossypin from Hibiscus vitifolius against global cerebral ischemia model in rats.
PubMed: Isolation of methyl 27-caffeoyloxyoleanolate--a new oleanane Triterpenoid from the roots of Hibiscus vitifolius.
PubMed: Gossypin as a novel selective dual inhibitor of V-RAF murine sarcoma viral oncogene homolog B1 and cyclin-dependent kinase 4 for melanoma.
PubMed: Gossypin induces G2/M arrest in human malignant glioma U251 cells by the activation of Chk1/Cdc25C pathway.
PubMed: Antidiabetic activity of gossypin, a pentahydroxyflavone glucoside, in streptozotocin-induced experimental diabetes in rats.
PubMed: [Effect of seven kinds of flavonoids on recombinant human protein tyrosine phosphatase].
PubMed: Evaluation of anti-allergic activity of gossypin and suramin in mast cell-mediated allergy model.
PubMed: Oral supplementation of gossypin during lead exposure protects alteration in heme synthesis pathway and brain oxidative stress in rats.
PubMed: The flavonoid glycosides, myricitrin, gossypin and naringin exert anxiolytic action in mice.
PubMed: Antiinflammatory and antinociceptive activities of gossypin and procumbentin--cyclooxygenase-2 (COX-2) inhibition studies.
PubMed: Gossypin up-regulates LDL receptor through activation of ERK pathway: a signaling mechanism for the hypocholesterolemic effect.
PubMed: Comparative evaluation of some flavonoids and tocopherol acetate against the systemic toxicity induced by sulphur mustard.
PubMed: Influence of some bioflavonoids on the transport of nitrendipine.
PubMed: A flavonoid gossypin binds to cyclin-dependent kinase 2.
PubMed: Prophylactic effect of gossypin against percutaneously administered sulfur mustard.
PubMed: Interaction of flavonoids and intestinal facilitated glucose transporters.
PubMed: Gossypin, a pentahydroxy glucosyl flavone, inhibits the transforming growth factor beta-activated kinase-1-mediated NF-kappaB activation pathway, leading to potentiation of apoptosis, suppression of invasion, and abrogation of osteoclastogenesis.
PubMed: Gossypin protects primary cultured rat cortical cells from oxidative stress- and beta-amyloid-induced toxicity.
PubMed: Free radical scavenging, antitumor and anticarcinogenic activity of gossypin.
PubMed: Interaction of hydrated electron with dietary flavonoids and phenolic acids: rate constants and transient spectra studied by pulse radiolysis.
PubMed: Influence of gossypin on the development of acute tolerance to morphine induced antinociception.
PubMed: A study on the role of cholinergic and gamma amino butyric acid systems in the anti-nociceptive effect of gossypin.
PubMed: Protective effects of phenolic compounds on CCl4-induced toxicity in isolated rat hepatocytes.
PubMed: Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids.
PubMed: Dermal intoxication of mice with bis(2-chloroethyl)sulphide and the protective effect of flavonoids.
PubMed: Possible development of dependence on gossypin: role of gossypin on morphine dependence.
PubMed: Inhibition of sheep platelet arachidonate metabolism by flavonoids from Spanish and Indian medicinal herbs.
PubMed: Loss of plasmid linked antibiotic resistance in Escherichia coli on treatment with some phenolic compounds.
PubMed: Anti-inflammatory and anti-allergic properties of flavonoids.
PubMed: Studies on possible tolerance and mechanism of gossypin analgesia.
PubMed: Flavonoid-induced delay in the small intestinal transit: possible mechanism of action.
PubMed: Gossypin-induced analgesia in mice.
PubMed: Effect of gossypin, a flavonoid, on the formation of galactose-induced cataracts in rats.
PubMed: SOME OBSERVATIONS ON THE INFLUENCE OF RUTIN AND GOSSYPIN IN EXPERIMENTAL FROST-BITE.
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