scutellarein
4H-1-benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-
Identification
| Name | scutellarein |
| IUPAC | 5,6,7-trihydroxy-2-(4-hydroxyphenyl)chromen-4-one |
| CAS Number | 529-53-3 |
| FDA UNII | P460GTI853 |
| Molecular Formula | C15 H10 O6 |
| Molecular Weight | 286.23990000 |
| MDL Number | MFCD00017692 |
| Nikkaji Number | J6.686I |
| XlogP3 | 1.40 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 642.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 482.00 °F. TCC ( 249.90 °C. ) (est) |
| logP (o/w) | 2.540 (est) |
| Soluble in | water, 234.2 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| 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 scutellarein usage levels up to | not for fragrance use. |
| Recommendation for scutellarein flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-
6-
hydroxyapigenin
4',5,6,7-
tetrahydroxyflavanone
5,6,7,4'-
tetrahydroxyflavone
5,6,7-
trihydroxy-2-(4-hydroxyphenyl)chromen-4-one
PubMed:
Chemical fingerprint and metabolic profile analysis of Citrus reticulate 'Chachi' decoction by HPLC-PDA-IT-MS(n) and HPLC-Quadrupole-Orbitrap-MS method.
PubMed:
Inhibitory Effects of Scutellarein on Proliferation of Human Lung Cancer A549 Cells through ERK and NFκB Mediated by the EGFR Pathway.
PubMed:
Effect of light, methyl jasmonate and cyclodextrin on production of phenolic compounds in hairy root cultures of Scutellaria lateriflora.
PubMed:
Nanosuspension Development of Scutellarein as an Active and Rapid Orally Absorbed Precursor of its BCS Class IV Glycoside Scutellarin.
PubMed:
Phytotoxic potential of Onopordum acanthium L. (Asteraceae).
PubMed:
Simultaneous determination of three glucuronide conjugates of scutellarein in rat plasma by LC-MS/MS for pharmacokinetic study of breviscapine.
PubMed:
Analysis of the transcriptome of Erigeron breviscapus uncovers putative scutellarin and chlorogenic acids biosynthetic genes and genetic markers.
PubMed:
Bioactive diterpenoids and flavonoids from the aerial parts of Scoparia dulcis.
PubMed:
The effects of wine-processing on ascending and descending: The distribution of flavonoids in rat tissues after oral administration of crude and wine-processed Radix scutellariae.
PubMed:
Syk/Src-targeted anti-inflammatory activity of Codariocalyx motorius ethanolic extract.
PubMed:
The influence of selected flavonoids from the leaves of Cirsium palustre (L.) Scop. on collagen expression in human skin fibroblasts.
PubMed:
[Non-taxoid chemical constituents from needles of Taxus cuspidata].
PubMed:
Host-guest inclusion system of scutellarein with 2-hydroxypropyl-beta-cyclodextrin: preparation, characterization, and anticancer activity.
PubMed:
Influence of the gastrointestinal microflora and efflux transporters on the absorption of scutellarin and scutellarein.
PubMed:
Neuroprotective effects of scutellarin and scutellarein on repeatedly cerebral ischemia-reperfusion in rats.
PubMed:
In vitro evidence of possible influence of scutellarein towards bile acids' metabolism.
PubMed:
Antioxidant capacity of the leaf extract obtained from Arrabidaea chica cultivated in Southern Brazil.
PubMed:
Two new phenolic glycosides from Gnaphalium affine D. Don and their anti-complementary activity.
PubMed:
[Study on the chemical constituents in Pouzolzia zeylanica].
PubMed:
Comparison of inhibition capability of scutellarein and scutellarin towards important liver UDP-glucuronosyltransferase (UGT) isoforms.
PubMed:
Effect of Siam weed extract and its bioactive component scutellarein tetramethyl ether on anti-inflammatory activity through NF-κB pathway.
PubMed:
Identification of flavone glucuronide isomers by metal complexation and tandem mass spectrometry: regioselectivity of uridine 5'-diphosphate-glucuronosyltransferase isozymes in the biotransformation of flavones.
PubMed:
Polar constituents composition of endemic Sideritis italica (MILL.) GREUTER et BURTER from Central Italy.
PubMed:
Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo.
PubMed:
Mannich bases of scutellarein as thrombin-inhibitors: design, synthesis, biological activity and solubility.
PubMed:
Phytochemical study of polyphenols in Perilla Frutescens as an antioxidant.
PubMed:
Synthesis and protective effect of scutellarein on focal cerebral ischemia/reperfusion in rats.
PubMed:
Benzoxazinoids from Scoparia dulcis (sweet broomweed) with antiproliferative activity against the DU-145 human prostate cancer cell line.
PubMed:
Development of chemical inhibitors of the SARS coronavirus: viral helicase as a potential target.
PubMed:
A Review on the Taxonomy, Ethnobotany, Chemistry and Pharmacology of Oroxylum indicum Vent.
PubMed:
A set of regioselective O-methyltransferases gives rise to the complex pattern of methoxylated flavones in sweet basil.
PubMed:
Mechanistic studies on the absorption and disposition of scutellarin in humans: selective OATP2B1-mediated hepatic uptake is a likely key determinant for its unique pharmacokinetic characteristics.
PubMed:
In vitro and in vivo structure and activity relationship analysis of polymethoxylated flavonoids: identifying sinensetin as a novel antiangiogenesis agent.
PubMed:
Identification of myricetin and scutellarein as novel chemical inhibitors of the SARS coronavirus helicase, nsP13.
PubMed:
Identification and analysis of the active phytochemicals from the anti-cancer botanical extract Bezielle.
PubMed:
[Flavonoids and nor-sesquiterpenes of Pedicularis densispica].
PubMed:
Polyphenolic compounds from flowers of Hibiscus rosa-sinensis Linn. and their inhibitory effect on alkaline phosphatase enzyme activity in vitro.
PubMed:
Synthesis and bio-activity evaluation of scutellarein as a potent agent for the therapy of ischemic cerebrovascular disease.
PubMed:
Effect of flavonoids from Prosthechea michuacana on carbon tetrachloride induced acute hepatotoxicity in mice.
PubMed:
Efficient synthesis of scutellarein.
PubMed:
Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry.
PubMed:
Absorption and disposition of scutellarin in rats: a pharmacokinetic explanation for the high exposure of its isomeric metabolite.
PubMed:
[Design, synthesis and anti-oxidative evaluation of L-amino acid prodrugs of scutellarein].
PubMed:
In-line monitoring of extraction process of scutellarein from Erigeron breviscapus (vant.) Hand-Mazz based on qualitative and quantitative uses of near-infrared spectroscopy.
PubMed:
Intestinal transport of scutellarein and scutellarin and first-pass metabolism by UDP-glucuronosyltransferase-mediated glucuronidation of scutellarein and hydrolysis of scutellarin.
PubMed:
Metabolic and pharmacokinetic studies of scutellarin in rat plasma, urine, and feces.
PubMed:
Inhibition and disaggregation of α-synuclein oligomers by natural polyphenolic compounds.
PubMed:
Monitoring of antisolvent crystallization of sodium scutellarein by combined FBRM-PVM-NIR.
PubMed:
Preparative separation of four individual flavonoids in Scutellaria barbata D. Don based on high selectivity polymeric adsorbents with different polarities.
PubMed:
Trans-chalcone: a novel small molecule inhibitor of mammalian alpha-amylase.
PubMed:
[Absorption and transportation characteristics of scutellarin and scutellarein across Caco-2 monolayer model].
PubMed:
Comprehensive review of Clerodendrum phlomidis: a traditionally used bitter.
PubMed:
[Advances in studies on pharmacokinetics of scutellarin and scutellarein].
PubMed:
Flavones and phenylpropanoids from a sedative extract of Lantana trifolia L.
PubMed:
Separation and purification of two flavone glucuronides from Erigeron multiradiatus (Lindl.) Benth with macroporous resins.
PubMed:
CYP1-mediated antiproliferative activity of dietary flavonoids in MDA-MB-468 breast cancer cells.
PubMed:
Activity of ladanein on leukemia cell lines and its occurrence in Marrubium vulgare.
PubMed:
[Chemical constituents from Hedyotis diffusa].
PubMed:
Antioxidant activities of polyphenols extracted from Perilla frutescens varieties.
PubMed:
Mechanism of CYP2C9 inhibition by flavones and flavonols.
PubMed:
The constituents of Anisomeles indica and their anti-inflammatory activities.
PubMed:
In vitro antitumor mechanisms of various Scutellaria extracts and constituent flavonoids.
PubMed:
Flavonoids and cinnamic acid derivatives as inhibitors of 17beta-hydroxysteroid dehydrogenase type 1.
PubMed:
Flavones and flavone glycosides from Halophila johnsonii.
PubMed:
Anti-inflammatory activity of the extracts and fractions from Erigeron multiradiatus through bioassay-guided procedures.
PubMed:
Scutellarein inhibits hypoxia- and moderately-high glucose-induced proliferation and VEGF expression in human retinal endothelial cells.
PubMed:
Metabolites of scutellarein in rat plasma.
PubMed:
Inhibitory effect of Erigeron breviscapus extract and its flavonoid components on GABA shunt enzymes.
PubMed:
Identification and quantification of flavonoids of Mexican oregano (Lippia graveolens) by LC-DAD-ESI/MS analysis.
PubMed:
Isolation and identification of ten metabolites of breviscapine in rat urine.
PubMed:
Identification of polymethoxylated flavones from green tangerine peel (Pericarpium Citri Reticulatae Viride) by chromatographic and spectroscopic techniques.
PubMed:
Two major urinary metabolites of scutellarin in rats.
PubMed:
[Study on bile excretion of scutellarein].
PubMed:
Pharmacokinetics and metabolism of the flavonoid scutellarin in humans after a single oral administration.
PubMed:
Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds.
PubMed:
Pharmacokinetics of scutellarin and its aglycone conjugated metabolites in rats.
PubMed:
Inhibitory effects of a chemically standardized extract from Scutellaria barbata in human colon cancer cell lines, LoVo.
PubMed:
Determination of aglycone conjugated metabolites of scutellarin in rat plasma by HPLC.
PubMed:
Validation of an HPLC method for the determination of scutellarin in rat plasma and its pharmacokinetics.
PubMed:
Antioxidant activity of citrus limonoids, flavonoids, and coumarins.
PubMed:
[Determination of scutellarin and rutin in Shenfukang capsules by reversed-phase high performance liquid chromatography].
PubMed:
Antagonistic effect of scutellarin on the toxicity of selenium in rat livers.
PubMed:
Protection against hydrogen peroxide-induced cytotoxicity in PC12 cells by scutellarin.
PubMed:
Study on pharmacokinetics of scutellarin in rabbits.
PubMed:
Metabolism of apigenin by rat liver phase I and phase ii enzymes and by isolated perfused rat liver.
PubMed:
Protective effects of scutellarin on superoxide-induced oxidative stress in rat cortical synaptosomes.
PubMed:
Study on metabolism of scutellarin in rats by HPLC-MS and HPLC-NMR.
PubMed:
Variations in lipophilic and vacuolar flavonoids among European Pulicaria species.
PubMed:
[Recognition of three classes of skullcaps by FTIR spectroscopy combined with artificial neural networks].
PubMed:
6-hydroxyflavonoids as alpha-glucosidase inhibitors from marjoram (Origanum majorana) leaves.
PubMed:
Identification of lipophilic flavones and flavonols by comparative HPLC, TLC and UV spectral analysis.
PubMed:
[Study on effects of scutellarin on scavenging reactive oxygen].
PubMed:
[Studies on flavone constituents of Erigeron breviscapus (Vant.) Hand.-Mazz].
PubMed:
Structure-activity relationships of flavonoids, isolated from Scutellaria baicalensis, binding to benzodiazepine site of GABA(A) receptor complex.
PubMed:
Scutellarein 4'-methyl ether glycosides as taxonomic markers in Teucridium and Tripora (Lamiaceae, Ajugoideae).
PubMed:
Ventricular remodeling by Scutellarein treatment in spontaneously hypertensive rats.
PubMed:
The role of lipophilic and polar flavonoids in the classification of temperate members of the Anthemideae.
PubMed:
Effects of Scutellarein on diabetic rat aorta.
PubMed:
Foliar flavonoids of Annonaceae from Brazil: taxonomic significance.
PubMed:
Cloning and expression of UDP-glucose: flavonoid 7-O-glucosyltransferase from hairy root cultures of Scutellaria baicalensis.
PubMed:
Purification and characterization of UDP-glucuronate: baicalein 7-O-glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures.
PubMed:
Metabolites of orally administered Perilla frutescens extract in rats and humans.
PubMed:
Interaction of flavones from the roots of Scutellaria baicalensis with the benzodiazepine site.
PubMed:
The flavonoids of Tanacetum parthenium and T. vulgare and their anti-inflammatory properties.
PubMed:
Simultaneous separation of flavanone glycosides and polymethoxylated flavones in citrus juices using liquid chromatography.
PubMed:
Influence of a series of natural flavonoids on free radical generating systems and oxidative stress.
PubMed:
Effects of flavonoids on Naja naja and human recombinant synovial phospholipases A2 and inflammatory responses in mice.
PubMed:
Diglucuronoflavones from purple leaves of Perilla ocimoides.
PubMed:
Effects of flavonoids on cyclic AMP phosphodiesterase and lipid mobilization in rat adipocytes.
PubMed:
Inhibition of reverse transcriptases by flavonoids.
PubMed:
C18 solid-phase isolation and high-performance liquid chromatography/ultraviolet diode array determination of fully methoxylated flavones in citrus juices.