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robinetin
4H-1-benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)- (9CI)

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Name:3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
CAS Number: 490-31-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-709-6
FDA UNII: KJ6DBC4U7E
Nikkaji Web:J1.551B
Beilstein Number:0308905
MDL:MFCD00016783
XlogP3-AA:1.60 (est)
Molecular Weight:302.23910000
Formula:C15 H10 O7
BioActivity Summary:listing
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
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
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 669.90 °C. @ 760.00 mm Hg (est)
Flash Point: 497.00 °F. TCC ( 258.60 °C. ) (est)
logP (o/w): 2.550 (est)
Soluble in:
 water, 4972 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Norkanugin 98%
BOC Sciences
For experimental / research use only.
ROBINETIN >98%
Odor: characteristic
Use: Robinetin is from the leaves of Robinia pseudacacia. It inhibits EYPC membrane lipid peroxidation and HbA glycosylation with high efficiency. It could lead to the occurrence of positive induced circular dichroism (ICD) bands in the near ultra-violet (UV) antioxidant/antiradical/anti-mutagenesis/anti-promotion
Carbosynth
For experimental / research use only.
Robinetin
Coompo
For experimental / research use only.
Robinetin from Plants ≥96%
Odor: characteristic
Use: Antioxidant and antiradical activities. Anti-mutagenesis and anti-promotion. Incorporation of robinetin molecules in the chiral environment of the β-CDxs strongly affects the electronic transitions of robinetin leading to the occurrence of positive induced circular dichroism (ICD) bands in the near ultra-violet (UV) region. Molecular mechanics calculations show that the inclusion complex with the chromone ring inserted into the β-CDx cavity is most favorable, in agreement with our spectroscopic data.
ExtraSynthese
For experimental / research use only.
Robinetin (HPLC) ≥99%
 
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 robinetin usage levels up to:
 not for fragrance use.
 
Recommendation for robinetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5281692
National Institute of Allergy and Infectious Diseases:Data
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
Chemidplus:0000490313
 
References:
 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281692
Pubchem (sid):134976285
 
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):C10177
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
4H-1-benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
4H-1-benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)- (9CI)
5-deoxymyricetin
3,7-dihydroxy-2-(3,4,5-trihydroxy-phenyl)-chromen-4-one
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4-benzopyrone
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
 flavone, 3,3',4',5',7-pentahydroxy-
5-hydroxyfisetin
 norkanugin
3,3',4',5',7-pentahydroxyflavone
 

Articles:

PubMed:Phenolic composition of vinegars over an accelerated aging process using different wood species (acacia, cherry, chestnut, and oak): effect of wood toasting.
PubMed:Polyphenols in red wine aged in acacia (Robinia pseudoacacia) and oak (Quercus petraea) wood barrels.
PubMed:Polyphenolic profile as a useful tool to identify the wood used in wine aging.
PubMed:Effect of toasting intensity at cooperage on phenolic compounds in acacia (Robinia pseudoacacia) heartwood.
PubMed:Binding of the bioflavonoid robinetin with model membranes and hemoglobin: Inhibition of lipid peroxidation and protein glycosylation.
PubMed:Effect of beta-cyclodextrin nanocavity confinement on the photophysics of robinetin.
PubMed:An in vitro and in silico study on the flavonoid-mediated modulation of the transport of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) through Caco-2 monolayers.
PubMed:Antimicrobial activity of flavonoids.
PubMed:Allelopathic potential of Robinia pseudo-acacia L.
PubMed:Effects of selected flavonoids and carotenoids on drug accumulation and apoptosis induction in multidrug-resistant colon cancer cells expressing MDR1/LRP.
PubMed:Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
PubMed:Kinetic study of flavonoid reactions with stable radicals.
PubMed:Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.
PubMed:Quercetin-induced apoptosis in colorectal tumor cells: possible role of EGF receptor signaling.
PubMed:Inhibition of mitochondrial respiration and cyanide-stimulated generation of reactive oxygen species by selected flavonoids.
PubMed:Protective effects of phenolic compounds on CCl4-induced toxicity in isolated rat hepatocytes.
PubMed:Superoxide scavenging properties of flavonoids in a non-enzymic system.
PubMed:Effect of plant flavonoids on microsome catalyzed reactions of aflatoxin B1 leading to activation and DNA adduct formation.
PubMed:Modulation by plant flavonoids and related phenolics of microsome catalyzed adduct formation between benzo[a]pyrene and DNA.
PubMed:Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol.
PubMed:Effect of ellagic acid and hydroxylated flavonoids on the tumorigenicity of benzo[a]pyrene and (+/-)-7 beta, 8 alpha-dihydroxy-9 alpha, 10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene on mouse skin and in the newborn mouse.
PubMed:Inhibition of the mutagenicity of bay-region diol-epoxides of polycyclic aromatic hydrocarbons by phenolic plant flavonoids.
PubMed:Mutagenicity of plant flavonols in the Salmonella/mammalian microsome test: activation of flavonol glycosides by mixed glycosidases from rat cecal bacteria and other sources.
PubMed:Metabolism of myricetin and related compounds in the rat. Metabolite formation in vivo and by the intestinal microflora in vitro.
 
Notes:
None found
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