492-14-8

Basic information

• Product Name: Butin
• Synonyms: (2S)-7,3',4'-Trihydroxyflavanone;(S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-2,3-dihydro-7-hydroxy-, (S)-;butin (7, 3′, 4′-trihydroxydihydroflavone);(2S)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one;(S)-7,3',4'-Trihydroxyflavanone;7, 3', 4'-trihydroxydihydroflavone
• CAS NO: 492-14-8
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.2528
• Mol File: 492-14-8.mol

Chemical Properties

• Melting Point: 224-226℃
• Boiling Point: 582.4 °C at 760 mmHg
• Flash Point: 226.7 °C
• Appearance: /
• Density: 1.485
• Vapor Pressure: 3.68E-14mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: 2-8°C
• PKA: 7.69±0.40(Predicted)
• CAS DataBase Reference: Butin(CAS DataBase Reference)
• NIST Chemistry Reference: Butin(492-14-8)
• EPA Substance Registry System: Butin(492-14-8)

Safety Data

• Hazardous Substances Data: 492-14-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Butin is used as a therapeutic agent for its potential to inhibit the growth of cancer cells, making it a candidate for cancer treatment. Its antioxidant and anti-inflammatory properties also contribute to its potential use in managing oxidative stress and inflammation-related conditions.
Used in Nutraceutical Industry:
Butin is used as a dietary supplement due to its health-promoting properties, including its antioxidant and anti-inflammatory effects, which can contribute to overall wellness and potentially reduce the risk of various diseases.
Used in Cosmetic Industry:
Butin is used as an ingredient in cosmetic products for its antioxidant properties, which can help protect the skin from oxidative damage and potentially slow down the aging process.
Used in Agricultural Industry:
Butin can be used in the development of natural pesticides or as a component in plant health products, leveraging its antioxidant properties to enhance plant resilience against environmental stressors.
These applications highlight the versatility of butin across different industries, underscoring its potential as a valuable compound for health, wellness, and other applications.

InChI:InChI=1/C15H12O5/c16-9-2-3-10-12(18)7-14(20-15(10)6-9)8-1-4-11(17)13(19)5-8/h1-6,14,16-17,19H,7H2/t14-/m0/s1

Upstream product

• 4382-36-9 (+)-Fustin 

Downstream Products

• 485-63-2 3',4',7-trihydroxyisoflavone 

Relevant articles and documents

Polyphenols from the bark of Rhus verniciflua and their biological evaluation on antitumor and anti-inflammatory activities

Bioassay-guided fractionation and chemical investigation of the extract of Rhus verniciflua bark resulted in the identification of six polyphenols, rhusopolyphenols A-F (1-6), together with four known compounds including (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3, 10-trihydrobenzopyrano[3,4-c]-2-benzopyran-1-one (7), peapolyphenol C (8), cilicione-b (9) and (αR)- α,3,4,2',4'-pentahydroxydihydrochalcone (10). The structures of these polyphenols were elucidated by spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, and their absolute configurations were further confirmed by a combination of chemical methods and CD data analysis. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15), and compounds 4-6, 9 and 10 showed antiproliferative activity against the tested cells, with IC50 values of 3.31-18.51 μM. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, the anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium of murine microglia BV-2 cells. Compounds 5 and 10 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells with IC 50 values of 28.90 and 12.70 μM, respectively.

Bioactive flavonoids of the flowers of Butea monosperma

One new dihydrochalcone, dihydromonospermoside (7), was isolated from the flowers of Butea monosperma together with three known chalcones, butein (2), monospermoside (4) and isoliquiritigenin (8), one flavone, 7,3',4'- trihydroxyflavone (6), four flavanon

Antioxidant study and assignments of NMR spectral data for 3′,4′,7-trihydroxyflavanone 3′,7-Di-O-β-D-glucopyranoside (butrin) and its hydrolyzed product

The NMR spectral data including high resolution 1H, 13C and 2D NMR for butrin, 3′,4′,7-trihydroxyflavanone 3′,7-di-O-β-D-glucopyranoside, isolated from flowers of Butea monosperma, are reported here for the first time. Butrin was hydrolyzed using b-glucosidase to butin in high yield. They were subjected to free radical scavenging test using 2,2-diphenyl-1-picrylhydrazyl (DPPH) spectrophotometric assay. At a dose of 4 × 10-8 mol of tested compounds, the percentage of reduced DPPH for butin was 14.5% while no reduction was observed for butrin (0%).

Photochemical Deoxygenation of an α-Ketol: The Dihydroflavonol-Flavanone Conversion

Irradiation of optically pure 2,3-trans-3-hydroxyflavanones in anhydrous ethyl acetate leads directly to free phenolic flavanone analogues with complete retention of configuration at C(2).Similarly their methyl ethers give the corresponding flavanones and flavones.The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.