21849-70-7

Basic information

• Product Name: BUTEIN
• Synonyms: 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-2-propen-1-on;2’,4’-dihydroxy-3-(3,4-dihydroxyphenyl)-acrylophenon;1-(2,4-DIHYDROXYPHENYL)-3-(3,4-DIHYDROXYPHENYL)-2-PROPEN-1-ONE;2',3,4,4'-TETRAHYDROCHALCONE;2',3,4,4'-TETRAHYDROXYCHALCONE;2',4',3,4-TETRAHYDROXYCHALCONE;3,4,2',4'-TETRAHYDROXYCHALCONE;BUTEIN
• CAS NO: 21849-70-7
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25
• Product Categories: Chalcones
• Mol File: 21849-70-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: 250-252℃
• Boiling Point: 560.9±50.0 °C(Predicted)
• Appearance: yellow/solid
• Density: 1.483±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO: >50 mg/mL
• PKA: 7.34±0.35(Predicted)
• Water Solubility: DMSO: >50 mg/mL
• CAS DataBase Reference: BUTEIN(CAS DataBase Reference)
• NIST Chemistry Reference: BUTEIN(21849-70-7)
• EPA Substance Registry System: BUTEIN(21849-70-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 21849-70-7(Hazardous Substances Data)

Usage

Description

BUTEIN, also known as 3,4,2',4'-tetrahydroxychalcone, is a naturally occurring flavonoid derived from the medicinal plant Butea monosperma. It possesses potent anti-inflammatory and antioxidant properties, making it a promising candidate for various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
BUTEIN is used as an anti-inflammatory agent for its ability to selectively inhibit nuclear factor-κB in activated human mast cells. This inhibition leads to the suppression of tumor necrosis factor-α, interleukin (IL)-6, and IL-8, which are key mediators of inflammation and immune responses. By modulating these pathways, BUTEIN demonstrates potential therapeutic benefits in treating various inflammatory conditions and diseases.
Additionally, BUTEIN's antioxidant properties make it a valuable compound for further research and development in the pharmaceutical industry, particularly for applications related to oxidative stress and its associated disorders.

Upstream product

• 503-17-3 dimethylacetylene 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 57601-14-6 2'-hydroxy-3,4,4'-trimethoxychalcone 
• 71186-67-9 3,4-diallyloxybenzaldehyde 
• 2079-52-9 1-(2,4-bis(allyloxy)phenyl)ethanone 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 6515-06-6 3,4-bis-methoxymethoxy-benzaldehyde 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 
• 128837-28-5 3,4-Di(ethoxymethoxy)benzaldehyde 
• 130639-81-5 (E)-3-[3,4-bis(tetrahydro-2H-pyran-2-yloxy)phenyl]-1-[2-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one 
• 61854-89-5 3,4-di-[(tetrahydro-2H-pyran-2-yl)oxy]-benzaldehyde 
• 136258-01-0 2',4'-bis(tetrahydropyran-2-yloxy)acetophenone 

Downstream Products

• 13745-22-7 (E)-4-(3-(2,4-diacetoxyphenyl)-3-oxoprop-1-en-1-yl)-1,2-phenylene diacetate 
• 21913-99-5 2-(3,4-dihydroxyphenyl)-7-hydroxychroman-4-one 
• 128837-30-9 2'-Hydroxy-4',3,4-triethoxymethoxychalkone 
• 4382-36-9 (+/-)-2,3-trans-fustin 
• 503-17-3 dimethylacetylene 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 108-46-3 recorcinol 
• 485-63-2 3',4',7-trihydroxyisoflavone 
• 100634-10-4 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)propane-1-one 
• 1428324-84-8 C₁₇H₁₆N₂O₅ 
• 775351-90-1 3'-dimethylallylbutein 
• 4382-36-9 3,7,3',4'-tetrahydroxyflavanone 
• 528-48-3 3,7,3',4'-tetrahydroxyflavone 

Relevant articles and documents

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Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells

Glutamate-induced neurotoxicity is characterized by cellular Ca2+ uptake, which is upstream of reactive oxygen species (ROS)-induced apoptosis signaling and MAPKs activation. In the present study, we synthesized isoliquiritigenin analogs with electron-donating and electron-withdrawing functional groups. These analogs were evaluated for neuroprotective effect against glutamate-induced neurotoxicity in HT22 cells. Among these analogs, compound BS11 was selected as a potent neuroprotective agent. Cellular Ca2+ concentration, ROS level, MAPKs activation and AIF translocation to the nucleus were increased upon treatment with 5 mM glutamate. In contrast, we identified that compound BS11 reduced the cellular Ca2+ concentration and ROS level upon glutamate exposure. Western blot analysis showed that MAPK activation was decreased by treatment with compound BS11. We further identified that cotreatment of compound BS11 and glutamate inhibited translocation of AIF to the nucleus.

Synthesis and evaluation of butein derivatives for in vitro and in vivo inflammatory response suppression in lymphedema

Herein, we demonstrate that butein (1) can prevent swelling in a murine lymphedema model by suppressing tumor necrosis factor α (TNF-α) production. Butein derivatives were synthesized and evaluated to identify compounds with in vitro anti-inflammatory activity. Among them, 20 μM of compounds 7j, 7m, and 14a showed 50percent suppression of TNF-α production in mouse peritoneal macrophages after lipopolysaccharide stimulation. Compound 14a, exhibited the strongest potency with an in vitro IC50 of 14.6 μM and suppressed limb volume by 70percent in a murine lymphedema model. The prodrug strategy enabled a six-fold increase in kinetic solubility of compound 1 and five-fold higher levels of active metabolite in the blood for compound 14a via oral administration in the pharmacokinetics study. We suggest that the compound 14a could be developed as a potential therapeutic agent targeting anti-inflammatory activity to alleviate lymphedema progression.