prunetin
4H-1-benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-
Identification
| Name | prunetin |
| IUPAC | 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one |
| CAS Number | 552-59-0 |
| EINECS | 209-018-5 |
| FDA UNII | 1TG4H5H11J |
| Molecular Formula | C16 H12 O5 |
| Molecular Weight | 284.26764000 |
| MDL Number | MFCD00016951 |
| Nikkaji Number | J61.257J |
| Beilstein | 0292155 |
Regulatory
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) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 > 2000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-
5,4'-
dihydroxy-7-methoxyisoflavone
iso
flavone, 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
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 FeâOâ 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.