548-82-3

Basic information

• Product Name: PINOBANKSIN
• Synonyms: PINOBANKSIN;(2R)-2,3-Dihydro-3β,5,7-trihydroxy-2α-phenyl-4H-1-benzopyran-4-one;(2R)-2α-Phenyl-2,3-dihydro-3β,5,7-trihydroxy-4H-1-benzopyran-4-one;Pibanksin;(2R,3R)-3,5,7-Trihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one;(2R,3R)-3,5,7-Trihydroxy-2-phenyl-chroman-4-one;(2R,3R)-3,5,7-Trihydroxyflavanone
• CAS NO: 548-82-3
• Molecular Formula: C₁₅H₁₂O₅
• Molecular Weight: 272.25
• Mol File: 548-82-3.mol
• Article Data: 2

Chemical Properties

• Melting Point: 173-175 °C(Solv: methanol (67-56-1))
• Boiling Point: 570.6°C at 760 mmHg
• Flash Point: 222°C
• Appearance: /
• Density: 1.497g/cm³
• Vapor Pressure: 7.33E-14mmHg at 25°C
• Refractive Index: 1.695
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.40±0.60(Predicted)
• Stability: Hygroscopic
• BRN: 91238
• CAS DataBase Reference: PINOBANKSIN(CAS DataBase Reference)
• NIST Chemistry Reference: PINOBANKSIN(548-82-3)
• EPA Substance Registry System: PINOBANKSIN(548-82-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 548-82-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 548-82-3 differently. You can refer to the following data:
1. rac-Pinobanksin is a dihydroflavonol that posesses antioxidant properties. Pinobanksin is most commonly found in propolis, a material utilized by bees in the construction of their hives.
2. Pinobanksin is an antioxidant α-tocopherol reducing bioflavonoid (dihydroflavonol) found in honey that may be used in studies of inhibitors of lipid peroxidation. Pinobanksin may be used as a reference material in analytical studies of the presence and identity of anti-oxidative phenolic compounds found in plants such as propolis gum.

Definition

ChEBI: A trihydroxyflavanone in which the three hydroxy substituents are located at positions 3, 5 and 7.

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

Upstream product

• 36804-11-2 2,4,6-tri-MOM phloracetophenone 
• 1133835-06-9 3,5,7-trihydroxy-2-phenylchroman-4-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 1221923-43-8 (S)-2-Methyl-butyric acid (2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-chroman-3-yl ester 

Relevant articles and documents

Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure-activity relationship

To explore the structure-activity relationships on the inhibitory activity of flavanonols against nitric oxide (NO) production in inflammatory cells, we synthesized 19 flavanonols which shared a common 3,5,7-trihydroxychroman scaffold. A range of substitutions was included in the B ring in order to investigate the structure-activity relationship. We also succeeded in isolating stereoisomers from 16 of the flavanonols using chiral column chromatography. The inhibitory effects of these compounds on NO production were examined in RAW 264.7 cells (a murine macrophage-like cell line), which were activated by lipopolysaccharide (LPS). We only observed inhibitory activity against NO production in (2R,3R) stereoisomers, while the inhibitory activities of (2S,3S) stereoisomers were significantly weaker. We also evaluated the free radical scavenging potential of the flavanonols using 1,1-diphenyl-2-picrylhydrazyl (DPPH). Each stereoisomer indicated the equivalent DPPH scavenging potential as expected. The radical scavenging activity was not correlated with the inhibitory activity against NO. The inhibition of NO production by flavanonols is stereospecific and cannot simply be explained by their radical scavenging activity. We propose the possible existence of a 'target' molecule for flavanonols which is involved in the production and/or regulation of NO in RAW 264.7 cells.