480-40-0

Basic information

• Product Name: Chrysin
• Synonyms: AKOS NCG1-0026;5,7-DIHYDROXYFLAVONE;5,7-dihydroxy-2-phenyl-4h-benzo[b]pyran-4-one;5,7-DIHYDROXY-2-PHENYL-CHROMEN-4-ONE;LABOTEST-BB LT00440772;CHRYSIN;CHRYSINE;Chrysin 99.0%min
• CAS NO: 480-40-0
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• EINECS: 207-549-7
• Product Categories: Biochemistry;Flavonoids;Pharmaceutical intermediate;chemical reagent;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Inhibitors;Intermediates;FINE Chemical & INTERMEDIATES;Di-substituted Flavones
• Mol File: 480-40-0.mol
• Article Data: 41

Chemical Properties

• Melting Point: 284-286 °C(lit.)
• Boiling Point: 357.45°C (rough estimate)
• Flash Point: 192.5 °C
• Appearance: Yellow/Crystalline Powder
• Density: 1.2693 (rough estimate)
• Vapor Pressure: 2.67E-10mmHg at 25°C
• Refractive Index: 1.4872 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.50±0.40(Predicted)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2256
• BRN: 233276
• CAS DataBase Reference: Chrysin(CAS DataBase Reference)
• NIST Chemistry Reference: Chrysin(480-40-0)
• EPA Substance Registry System: Chrysin(480-40-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: LK8329050
• F: 10
• HazardClass: IRRITANT
• Hazardous Substances Data: 480-40-0(Hazardous Substances Data)

Usage

Chemical Description

Chrysin is a flavone found in honey and propolis.

Prepration

The main sources of chrysin are honey and propolis, of which the content of chrysin in honey is 5.3 mg/kg?and that in propolis is 28 g/L. In addition, chrysin is also found in various vegetables, fruits, herbs, and even mushrooms?[10]. Another source of populin is an endophytic fungus Chaetomium globosum, which is related to Chaetomorpha media from India. In addition, chrysin exists in the form of glycosides in walnut, walnut skin, walnut flower and pericarp passion fruit, and in the form of 6-c-arabinoside-8-c-glucoside or glucuronic acid ester in Pinellia ternata.

Description

Chrysin is a natural flavonoid with antioxidant, anti-inflammatory, and anticancer properties. It blocks COX-2 gene expression, PGE2 production, and hydroxyl radical formation in LPS-induced RAW 264.7 cells. Chrysin inhibits insulin-induced HIF-1α expression (~50% at 10 μM) in human prostate cancer DU145 cells and blocks DU145 xenograft-induced angiogenesis in vivo. In a mouse model of ischemia/reperfusion injury, chrysin decreased pro-inflammatory gene expression and oxidative stress, resulting in a reduction of infarct volume and neurological defects.

Physical properties

beige powder

Uses

Different sources of media describe the Uses of 480-40-0 differently. You can refer to the following data:
1. Chrysin is a flavanoid with anti-inflammatory effect and potential protective effects against cancer and cardiovascular disease. Studies show that Chrysin is central benzodiazepine receptor ligand wit h possible anxiolytic effects. Chrysin was initially believed to have aromatase inhibitor but recent in vivo studies have disproved that.
2. Chrysin is a flavanoid with anti-inflammatory effect and potential protective effects against cancer and cardiovascular disease. Studies show that Chrysin is central benzodiazepine receptor ligand with possible anxiolytic effects. Chrysin was initially believed to have aromatase inhibitor but recent in vivo studies have disproved that. Dyes and metabolites.

Definition

ChEBI: A dihydroxyflavone in which the two hydroxy groups are located at positions 5 and 7.

InChI:InChI=1/C15H10O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-8,16-17H

Upstream product

• 6665-78-7 5,7-di-O-acetyl chrysin 
• 103269-01-8 3-benzoyl-5,7-bis-benzoyloxy-2-phenyl-chromen-4-one 
• 532-32-1 sodium benzoate 
• 3602-54-8 4,6-dihydroxy-2-methoxyacetophenone 
• 93-97-0 benzoic acid anhydride 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 856406-49-0 3-benzoyl-5,7-dihydroxy-2-phenyl-chromen-4-one 
• 108-73-6 3,5-dihydroxyphenol 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 273211-30-6 1-phenyl-3-(2,4,6-trimethoxy-phenyl)-propane-1,3-dione 
• 480-39-7 pinocembrin 
• 104-55-2 3-phenyl-propenal 
• 6665-86-7 7-hydroxyflavone 
• 102-92-1 cinnamoyl chloride 

Downstream Products

• 144-62-7 oxalic acid 
• 65-85-0 benzoic acid 
• 108-73-6 3,5-dihydroxyphenol 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 
• 4443-09-8 norwogonin 
• 32140-66-2 2,5-dihydroxy-6,8-dichloroflavone 
• 84212-46-4 ethyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate 

Relevant articles and documents

Oxidation of Flavone, 5-Hydroxyflavone, and 5,7-Dihydroxyflavone to Mono-, Di-, and Tri-Hydroxyflavones by Human Cytochrome P450 Enzymes

Biologically active plant flavonoids, including 5,7-dihydroxyflavone (57diOHF, chrysin), 4′,5,7-trihydroxyflavone (4′57triOHF, apigenin), and 5,6,7-trihydroxyflavone (567triOHF, baicalein), have important pharmacological and toxicological significance, e.g., antiallergic, anti-inflammatory, antioxidative, antimicrobial, and antitumorgenic properties. In order to better understand the metabolism of these flavonoids in humans, we examined the oxidation of flavone, 5-hydroxyflavone (5OHF), and 57diOHF to various products by human cytochrome P450 (P450 or CYP) and liver microsomal enzymes. Individual human P450s and liver microsomes oxidized flavone to 6-hydroxyflavone, small amounts of 5OHF, and 11 other monohydroxylated products at different rates and also produced several dihydroxylated products (including 57diOHF and 7,8-dihydroxyflavone) from flavone. We also found that 5OHF was oxidized by several P450 enzymes and human liver microsomes to 57diOHF and further to 567triOHF, but the turnover rates in these reactions were low. Interestingly, both CYP1B1.1 and 1B1.3 converted 57diOHF to 567triOHF at turnover rates (on the basis of P450 contents) of >3.0 min-1, and CYP1A1 and 1A2 produced 567triOHF at rates of 0.51 and 0.72 min-1, respectively. CYP2A13 and 2A6 catalyzed the oxidation of 57diOHF to 4′57triOHF at rates of 0.7 and 0.1 min-1, respectively. Our present results show that different P450s have individual roles in oxidizing these phytochemical flavonoids and that these reactions may cause changes in their biological and toxicological properties in mammals.

Novel chromenone derivatives having substituted biphenyl group and a pharmaceutical composition for prevention or treatment of allergic diseases compring the same

The present invention relates to: a novel chromenone derivative compound capable of effectively suppressing an allergic immune response by inhibiting signal transduction mediated by thymic stromal lymphopoietin (TSLP); and a pharmaceutical composition capable of fundamentally preventing or treating various allergic diseases by using the same.COPYRIGHT KIPO 2021

Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease

Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.