480-37-5

Basic information

• Product Name: Pinostrobin
• Synonyms: 2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one;2-Phenyl-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one;Pinostobin;Pistrobin;Pinostrobin,(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one;PINOCEMBRIN-7-METHYLETHER(RG)(PLEASE CALL);(S)-2,3-DIHYDRO-5-HYDROXY-7-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE;PINOSTROBIN
• CAS NO: 480-37-5
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• EINECS: 207-548-1
• Product Categories: Flavanones
• Mol File: 480-37-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 100°C
• Boiling Point: 494.9 °C at 760 mmHg
• Flash Point: 188.8 °C
• Appearance: /
• Density: 1.284 g/cm³
• Vapor Pressure: 2.03E-10mmHg at 25°C
• Refractive Index: 1.612
• Storage Temp.: 2-8°C
• PKA: 7.40±0.40(Predicted)
• CAS DataBase Reference: Pinostrobin(CAS DataBase Reference)
• NIST Chemistry Reference: Pinostrobin(480-37-5)
• EPA Substance Registry System: Pinostrobin(480-37-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 480-37-5(Hazardous Substances Data)

Usage

Description

Pinostrobin is a flavonoid with diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties. It induces quinone reductase (QR) in murine hepatoma cells with a QR doubling concentration of 500 nM. Pinostrobin inhibits TNF-α and IL-1β production in RAW 264.7 macrophages (IC50s = 17.28 and 23.5 μM, respectively) and in LPS-stimulated rats (48.6 and 55% reduction, respectively). Pinostrobin also shows selective cytotoxicity for CCRF-CEM leukemia cells (IC50 = 10.2 μM) in a panel of eight cancer cell lines (IC50s = >30 μM).

Definition

ChEBI: A monohydroxyflavanone that is (2S)-flavanone substituted by a hydroxy group at position 5 and a methoxy group at position 7 respectively.

InChI:InChI=1/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3

Upstream product

• 115799-14-9 pinostrobin 5-O-β-D-glucopyranoside 
• 186581-53-3 diazomethane 
• 1036-72-2 Pinocembrin dimethyl ether 
• 500-99-2 3,5-dimethoxyphenol 
• 72656-47-4 ethyl (R)-3-hydroxy-3-phenylpropanoate 
• 271600-97-6 3,5-dimethoxyphenyl-1-methoxymethyl ether 
• 351458-82-7 (R)-3-(tert-butyldimethylsylil)oxy-N-methoxy-N-methyl-benzenepropanamide 
• 131294-12-7 ethyl [(3R)-(tert-butyldimethylsilyloxy)-3-phenyl]propionate 
• 862254-91-9 (R)-3-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropan-1-one 
• 351458-87-2 (R)-1-[2,4-dimethoxy-6-(methoxymethoxy)phenyl]-3-phenyl-3-(tert-butyldimethylsilyl)oxy-propan-1-one 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 187877-87-8 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 59887-91-1 5,7-dimethoxy-4H-chromen-4-one 
• 98-80-6 phenylboronic acid 

Downstream Products

• 612836-69-8 pinostrobin oxime 

Relevant articles and documents

Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition

An efficient synthesis of bioactive chiral flavanones (1) was achieved through the αh-catalyzed asymmetric 1,4-addition of arylboronic acid to chromone. The reaction in toluene proceeded smoothly at room temperature in the presence of 0.5% Rh catalyst with electron-poor chiral diphosphine MeO-F 12-BIPHEP. In this reaction, the 1,2-addition to (S)-1 frequently occurred to yield (2S,4α)-2,4-diaryl-4-chromanol as a byproduct, which could be reduced by changing the reaction solvent to CH2C 12 to deactivate the Rh catalyst (3% required).

Approaches to 2-substituted chroman-4-ones: Synthesis of (-)-pinostrobin

Two approaches to optically active 2-substituted chroman-4-ones are described. The first utilized the oxidation of a preformed chroman ring and the second an intramolecular Mitsunobu cyclization. The methodology was applied to the synthesis of the biologically active natural product (-)-pinostrobin (18).