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

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

Used in Antioxidant Applications:
PINOBANKSIN is used as an antioxidant agent for its ability to reduce lipid peroxidation. It plays a crucial role in protecting cells from oxidative stress and damage, which can lead to various diseases and aging.
Used in Pharmaceutical Research:
PINOBANKSIN is used as a reference material in the pharmaceutical industry for analytical studies of the presence and identity of anti-oxidative phenolic compounds found in plants such as propolis gum. This helps in the development of new drugs and therapies based on the antioxidant properties of PINOBANKSIN.
Used in the Honey Industry:
In the honey industry, PINOBANKSIN is used as an indicator of the quality and authenticity of honey. Its presence in honey signifies the presence of bioactive compounds derived from propolis, which contribute to the overall health benefits of honey.
Used in Cosmetics:
PINOBANKSIN may be used in the cosmetics industry for its antioxidant and anti-aging properties. It can be incorporated into skincare products to help protect the skin from environmental stressors and promote a youthful appearance.
Used in Analytical Chemistry:
PINOBANKSIN is used as a reference compound in analytical chemistry for the identification and quantification of phenolic compounds in various samples, including plant extracts and natural products. This aids in the quality control and standardization of these products.

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.

Constituents of Chinese propolis and their antiproliferative activities

Two new flavonoids, 3-O-[(S)-2-methylbutyroyl] pinobanksin (1) and 6-cinnamylchrysin (2), were isolated from the EtOAc-soluble fraction of the MeOH extract of Chinese propolis, along with 12 known compounds (3-14). The structures of the isolated compounds were elucidated on the basis of spectroscopic and chemical analyses. The isolated compounds were tested for their antiproliferative activity toward five different cancer cell lines. Benzyl caffeate (13) and phenethyl caffeate (14) showed potent antiproliferative activity toward tested cell lines with a selective activity toward colon 26-L5 carcinoma cell line (EC50 values: 13, 1.01; 14, 0.30 μM).