baicalein

5,6,7-trihydroxyflavone

CAS: 491-67-8 C15 H10 O5 MW: 270.24070000

Identification

Namebaicalein
IUPAC5,6,7-trihydroxy-2-phenylchromen-4-one
CAS Number491-67-8
FDA UNII49QAH60606
Molecular FormulaC15 H10 O5
Molecular Weight270.24070000
MDL NumberMFCD00017459
Nikkaji NumberJ22.048E
Beilstein0272683
XlogP31.70 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 264.50 °C. @ 760.00 mm Hg
Boiling Point 575.90 °C. @ 760.00 mm Hg (est)
Flash Point 438.00 °F. TCC ( 225.30 °C. ) (est)
logP (o/w) 3.310 (est)
Soluble in water, 112.5 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for baicalein usage levels up tonot for fragrance use.
Recommendation for baicalein flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

skullcap baikal skullcap root

Synonyms

baikalein biacalein noroxylin 5,6,7- trihydroxy-2-phenylchromen-4-one 5,6,7- trihydroxyflavone PubMed: Prophylactic effect of baicalein against renal dysfunction in type 2 diabetic rats. PubMed: Baicalein Protects against Type 2 Diabetes via Promoting Islet β-Cell Function in Obese Diabetic Mice. PubMed: Differential effects of baicalein and its sulfated derivatives in inhibiting proliferation of human breast cancer MCF-7 cells. PubMed: [Baicalein induces HeLa cell growth inhibition by down-regulation of matrix metalloproteinases and activating extracellular signal-regulated kinase]. PubMed: Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of black (Tuber aestivum Vittad.) and white (Tuber magnatum Pico) truffles. PubMed: Effects of chemopreventive natural products on non-homologous end-joining DNA double-strand break repair. PubMed: Baicalein modulates Nrf2/Keap1 system in both Keap1-dependent and Keap1-independent mechanisms. PubMed: Skullcap (Scutellaria baicalensis) extract and its active compound, wogonin, inhibit ovalbumin-induced Th2-mediated response. PubMed: Baicalein inhibits lipid accumulation by regulating early adipogenesis and m-TOR signaling. PubMed: Antidepressant-like effects of Xiaochaihutang in a rat model of chronic unpredictable mild stress. PubMed: 5,6,7-trimethoxyflavone suppresses pro-inflammatory mediators in lipopolysaccharide-induced RAW 264.7 macrophages and protects mice from lethal endotoxin shock. PubMed: Synergistic Action of Flavonoids, Baicalein, and Daidzein in Estrogenic and Neuroprotective Effects: A Development of Potential Health Products and Therapeutic Drugs against Alzheimer's Disease. PubMed: HPLC and chemometrics for the quality consistency evaluation of Shuanghuanglian injection. PubMed: Bioconversion of flavones during fermentation in milk containing Scutellaria baicalensis extract by Lactobacillus brevis. PubMed: Inhibitory effect of skullcap (Scutellaria baicalensis) extract on ovalbumin permeation in vitro and in vivo. PubMed: Inhibitory effect of baicalin and baicalein on ovarian cancer cells. 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: Molecular effects of baicalein in Hct116 cells and Caenorhabditis elegans : activation of the Nrf2 signaling pathway and prolongation of lifespan. PubMed: Effects of baicalein on apoptosis, cell cycle arrest, migration and invasion of osteosarcoma cells. PubMed: Anti-inflammatory effect of Sosihotang via inhibition of nuclear factor-κB and mitogen-activated protein kinases signaling pathways in lipopolysaccharide-stimulated RAW 264.7 macrophage cells. PubMed: Baicalein protects against 6-OHDA-induced neurotoxicity through activation of Keap1/Nrf2/HO-1 and involving PKCα and PI3K/AKT signaling pathways. PubMed: The role of intestinal microflora in anti-inflammatory effect of baicalin in mice. PubMed: Protective effects of baicalein against excess L-DOPA-induced dopamine quinone neurotoxicity. PubMed: FDA-approved drugs that protect mammalian neurons from glucose toxicity slow aging dependent on cbp and protect against proteotoxicity. PubMed: Study of the chemical composition and antimicrobial activities of ethanolic extracts from roots of Scutellaria baicalensis Georgi. PubMed: Evaluation of antioxidant and inhibitory activities for different subclasses flavonoids on enzymes for rheumatoid arthritis. PubMed: Structure-metabolism relationships for the glucuronidation of flavonoids by UGT1A3 and UGT1A9. PubMed: Thermodynamic versus kinetic control of antioxidant synergism between β-carotene and (iso)flavonoids and their glycosides in liposomes. PubMed: [Study on optimizing prescription of baicalein long circulating liposomes]. PubMed: Structure-affinity relationship of flavones on binding to serum albumins: effect of hydroxyl groups on ring A. PubMed: Dietary flavonoids activate the constitutive androstane receptor (CAR). PubMed: Glycosylation of dietary flavonoids decreases the affinities for plasma protein. PubMed: Antihepatotoxic effect of corn peptides against Bacillus Calmette-Guerin/lipopolysaccharide-induced liver injury in mice. PubMed: Synergistic anti-cancer effect of baicalein and silymarin on human hepatoma HepG2 Cells. PubMed: Multiple compounds determination and fingerprint analysis of Lidanpaishi tablet and keli by high-performance liquid chromatography. PubMed: Sodium borohydride/chloranil-based assay for quantifying total flavonoids. PubMed: Baicalein inhibits osteoclast differentiation and induces mature osteoclast apoptosis. PubMed: Biotransformation of ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, hesperidin, poncirin, glycyrrhizin, and baicalin by human fecal microflora and its relation to cytotoxicity against tumor cells. PubMed: Comparison of the major flavonoid content of S. baicalensis, S. lateriflora, and their commercial products. PubMed: Synthesis and biological evaluation of novel C(6) modified baicalein derivatives as antioxidative agents. PubMed: Cytoprotective effect of baicalein against peroxynitrite-induced toxicity in LLC-PK(1) cells. PubMed: [Effects of flavonoids with different structures on proliferation of leukemia cell line HL-60]. PubMed: Influence of food polyphenols on aryl hydrocarbon receptor-signaling pathway estimated by in vitro bioassay. PubMed: Chemopreventive effects of minor dietary constituents in common foods on human cancer cells. PubMed: Baicalein, a flavonoid extracted from a methanolic extract of Oroxylum indicum inhibits proliferation of a cancer cell line in vitro via induction of apoptosis. PubMed: Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death. PubMed: Baicalein induction of hydroxyl radical formation via 12-lipoxygenase in human platelets: an ESR study. PubMed: Wogonin suppresses TNF-alpha-induced MMP-9 expression by blocking the NF-kappaB activation via MAPK signaling pathways in human aortic smooth muscle cells. PubMed: Inhibition of 12-lipoxygenase during baicalein-induced human lung nonsmall carcinoma H460 cell apoptosis. PubMed: Assessing 12(S)-lipoxygenase inhibitory activity using colorectal cancer cells overexpressing the enzyme. PubMed: Baicalein inhibits adipocyte differentiation by enhancing COX-2 expression. PubMed: Beneficial effect of flavonoid baicalein in cisplatin-induced cell death of human glioma cells. PubMed: Ultrasound-assisted extraction methodology as a tool to improve the antioxidant properties of herbal drug Xiao-chia-hu-tang. PubMed: alpha-Glucosidase inhibition of 6-hydroxyflavones. Part 3: Synthesis and evaluation of 2,3,4-trihydroxybenzoyl-containing flavonoid analogs and 6-aminoflavones as alpha-glucosidase inhibitors. PubMed: Importance of the B ring and its substitution on the alpha-glucosidase inhibitory activity of baicalein, 5,6,7-trihydroxyflavone. PubMed: Potent Inhibitory effect of flavonoids in Scutellaria baicalensis on amyloid beta protein-induced neurotoxicity. PubMed: Kinetic study of flavonoid reactions with stable radicals. PubMed: Effects of Sho-saiko-to extract and its components, Baicalin, baicalein, glycyrrhizin and glycyrrhetic acid, on pharmacokinetic behavior of salicylamide in carbon tetrachloride intoxicated rats. PubMed: Structure-activity relationships for alpha-glucosidase inhibition of baicalein, 5,6,7-trihydroxyflavone: the effect of A-ring substitution. PubMed: Flavonoids as aryl hydrocarbon receptor agonists/antagonists: effects of structure and cell context. PubMed: Baicalein induced in vitro apoptosis undergo caspases activity in human promyelocytic leukemia HL-60 cells. PubMed: Insect antifeedant activity of flavones and chromones against Spodoptera litura. PubMed: Inhibition of thyroid type 1 deiodinase activity by flavonoids. PubMed: Effects of scutellariae radix extract and its components (baicalein, baicalin, and wogonin) on the experimental elevation of aqueous flare in pigmented rabbits. PubMed: Effect of Sho-saiko-to extract on HGF and TGF-beta levels of intraorgans in liver-injured rats after partial hepatectomy. PubMed: Effects of Sho-saiko-to extract on liver fibrosis in relation to the changes in hydroxyproline and retinoid levels of the liver in rats.