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
• Article Data: 4

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

General Description

Butin, also known as 3,4,5-trihydroxy-trans-stilbene, is a natural chemical compound found in certain plants, including Rhus succedanea and Toxicodendron vernicifluum. It belongs to the stilbene group of compounds and is known for its antioxidant and anti-inflammatory properties. Butin has been studied for its potential therapeutic effects, including its ability to inhibit the growth of cancer cells, protect against oxidative stress, and reduce inflammation. Additionally, it has been investigated for its potential use in the treatment of various diseases, including cancer, diabetes, and cardiovascular disorders. Overall, butin shows promise as a potential medicinal compound with various potential health benefits.

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.

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%).