EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

prunetin
4H-1-benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-

Supplier Sponsors

Name:5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
CAS Number: 552-59-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:209-018-5
FDA UNII: 1TG4H5H11J
Nikkaji Web:J61.257J
Beilstein Number:0292155
MDL:MFCD00016951
XlogP3-AA:3.00 (est)
Molecular Weight:284.26764000
Formula:C16 H12 O5
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
Melting Point: 239.50 °C. @ 760.00 mm Hg
Boiling Point: 546.50 °C. @ 760.00 mm Hg (est)
Flash Point: 409.00 °F. TCC ( 209.70 °C. ) (est)
logP (o/w): 3.530 (est)
Soluble in:
 water, 71.1 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.
Prunetin 98%
BOC Sciences
For experimental / research use only.
Prunetin >98%
Odor: characteristic
Use: Prunetin is a flavonoid compound found in the herbs of Millettia dielsiana. Prunetin has been isolated for the first time by Finnemore in 1910.
ExtraSynthese
For experimental / research use only.
Prunetin (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Prunetin ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
Prunetin ≥98.0% (TLC)
sds
 
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:
intraperitoneal-mouse LD50 > 2000 mg/kg
Pharmaceutical Chemistry Journal Vol. 13, Pg. 51, 1979.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for prunetin usage levels up to:
 not for fragrance use.
 
Recommendation for prunetin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Preparatory work to support the risk assessment for peri- and postmenopausal women taking food supplements containing isolated isoflavones
View page or View pdf

Risk assessment for peri- and post-menopausal women taking food supplements containing isolated isoflavones
View page or View pdf

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 :5281804
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
Chemidplus:0000552590
RTECS:DJ3100050 for cas# 552-59-0
 
References:
 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5281804
Pubchem (sid):135024846
 
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):C10521
HMDB (The Human Metabolome Database):HMDB34127
FooDB:FDB012400
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
 cherry sour cherry fruit
Search Trop Picture
 clover red clover
Search Trop Picture
 licorice
Search Trop Picture
 prunus spp
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-
5,4'-dihydroxy-7-methoxyisoflavone
isoflavone, 4',5-dihydroxy-7-methoxy- (7CI,8CI)
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one
 prunetin (6CI)
 prunusetin
 

Articles:

PubMed:Prunus yedoensis bark inhibits lipopolysaccharide-induced inflammatory cytokine synthesis by IκBα degradation and MAPK activation in macrophages.
PubMed:Biochanin A and prunetin improve epithelial barrier function in intestinal CaCo-2 cells via downregulation of ERK, NF-κB, and tyrosine phosphorylation.
PubMed:Effect of Prunetin on TNF-α-Induced MUC5AC Mucin Gene Expression, Production, Degradation of IκB and Translocation of NF-κB p65 in Human Airway Epithelial Cells.
PubMed:The isoflavone irilone contributes to the estrogenic potential of dietary supplements containing red clover.
PubMed:On the radical scavenging activity of isoflavones: thermodynamics of O-H bond cleavage.
PubMed:Anti-inflammatory effect of prunetin via the suppression of NF-κB pathway.
PubMed:Molecular mechanisms underlying the anti-obesity potential of prunetin, an O-methylated isoflavone.
PubMed:Inhibitory effects of isoflavonoids on rat prostate testosterone 5α-reductase.
PubMed:A Review on the Taxonomy, Ethnobotany, Chemistry and Pharmacology of Oroxylum indicum Vent.
PubMed:Effects of feeding dairy cows different legume-grass silages on milk phytoestrogen concentration.
PubMed:Screening and identification of BSA bound ligands from Puerariae lobata flower by BSA functionalized Fe₃O₄ magnetic nanoparticles coupled with HPLC-MS/MS.
PubMed:Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase.
PubMed:[Study on HPLC chromatographic fingerprint of anti-tumor active site SSCE of Caulis spatholobi].
PubMed:Secondary metabolites from the roots of Neolitsea daibuensis and their anti-inflammatory activity.
PubMed:Analysis of 5-hydroxyisoflavones by surface-enhanced Raman spectroscopy: genistein and methoxy derivatives.
PubMed:Isoflavones as apoptosis inducers in human hepatoma HuH-7 cells.
PubMed:Antimicrobial activities of the CH2Cl2-CH3OH (1:1) extracts and compounds from the roots and fruits of Pycnanthus angolensis (Myristicaceae).
PubMed:Inhibition of secretion, production and gene expression of mucin from cultured airway epithelial cells by prunetin.
PubMed:Electrospray ionization Fourier transform ion cyclotron resonance mass spectrometric and semi-empirical calculations study of five isoflavone aglycones.
PubMed:Secondary metabolites and antimycobacterial activities from the roots of Ficus nervosa.
PubMed:Isoflavones isolated from red clover (Trifolium pratense) inhibit smooth muscle contraction of the isolated rat prostate gland.
PubMed:Absorption of red clover isoflavones in human subjects: results from a pilot study.
PubMed:Gas chromatographic-mass spectrometric fragmentation study of phytoestrogens as their trimethylsilyl derivatives: identification in soy milk and wastewater samples.
PubMed:Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones.
PubMed:[Isoflavone glycosides from the bark of Maackia amurensis].
PubMed:Disposition of flavonoids via enteric recycling: UDP-glucuronosyltransferase (UGT) 1As deficiency in Gunn rats is compensated by increases in UGT2Bs activities.
PubMed:[Studies on chemical constituents of Primula sikkmensis].
PubMed:Flavonoid-responsive nodY-lacZ expression in three phylogenetically different Bradyrhizobium groups.
PubMed:NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.
PubMed:Disposition of flavonoids via enteric recycling: enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms.
PubMed:Rapid-resolution HPLC with spectrometric detection for the determination and identification of isoflavones in soy preparations and plant extracts.
PubMed:Amorphane sesquiterpenes from a marine Streptomyces sp.
PubMed:Pycnanthuquinone C: a new terpenoid-quinone from Pycnanthus angolensis.
PubMed:Cytotoxic constituents from Butea superba Roxb.
PubMed:Disposition of flavonoids via enteric recycling: structural effects and lack of correlations between in vitro and in situ metabolic properties.
PubMed:Isoflavone profiles of red clovers and their distribution in different parts harvested at different growing stages.
PubMed:Isoflavonoids are present in Arabidopsis thaliana despite the absence of any homologue to known isoflavonoid synthases.
PubMed:Determination of isoflavones in dietary supplements containing soy, Red Clover and kudzu: extraction followed by basic or acid hydrolysis.
PubMed:Dalsympathetin--a new isoflavone gentiobioside from Dalbergia sympathetica (Dennst.).
PubMed:Disposition of flavonoids via recycling: comparison of intestinal versus hepatic disposition.
PubMed:Immunoassay for biochanin A.
PubMed:Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species.
PubMed:Inhibitory effects of flavonoids on phosphodiesterase isozymes from guinea pig and their structure-activity relationships.
PubMed:Absorption and metabolism of genistein and its five isoflavone analogs in the human intestinal Caco-2 model.
PubMed:Assessment of the reactivity of selected isoflavones against proteins in comparison to quercetin.
PubMed:Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury.
PubMed:Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection.
PubMed:Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.
PubMed:Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry.
PubMed:Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells.
PubMed:In vitro antioxidant activity of some selected Prunus species in Korea.
PubMed:A new coumaronochromone from Sophora japonica.
PubMed:Triflavonoids of Ochna calodendron.
PubMed:Four new isoflavone triglycosides from Sophora japonica.
PubMed:Effect of enzyme inhibitors on protein quaternary structure determined by on-line size exclusion chromatography-microelectrospray ionization mass spectrometry.
PubMed:Antiplasmodial activity of isoflavones from Andira inermis.
PubMed:An isoflavone from Myristica malabarica.
PubMed:Allosteric inhibition of human liver aldehyde dehydrogenase by the isoflavone prunetin.
PubMed:TPK inhibitors differentially affect IFN-gamma activities.
PubMed:Flavonoids as DNA topoisomerase antagonists and poisons: structure-activity relationships.
PubMed:Biochemical studies of a new class of alcohol dehydrogenase inhibitors from Radix puerariae.
PubMed:Daidzin: a potent, selective inhibitor of human mitochondrial aldehyde dehydrogenase.
PubMed:Inhibition of herpes simplex virus replication by genistein, an inhibitor of protein-tyrosine kinase.
PubMed:Impurity in a common growth medium component: presence of an isoflavonoid in samples of L-asparagine.
PubMed:A synthesis of prunetin.
 
Notes:
reduces herpes virus-1 plaque formation. Occurs in several Prunus spp. and Glycyrrhiza glabra (licorice)
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