480-39-7

Basic information

• Product Name: PINOCEMBRIN
• Synonyms: 5,7-DIHYDROXYFLAVANONE;5,7-DIHYDROXY-3'4'5'-FLAVANONE;5,7-DIHYDROXY-2-PHENYL-CHROMAN-4-ONE;PINOCEMBRIN;(s)-2,3-dihydro-5,7-dihydroxy-2-phenyl-4h-1-benzopyran-4-one;3-dihydro-5,7-dihydroxy-2-phenyl-(s)-4h-1-benzopyran-4-on;dihydrochrysin;galanginflavanone
• CAS NO: 480-39-7
• Molecular Formula: C₁₅H₁₂O₄
• Molecular Weight: 256.25
• Product Categories: Flavanones;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Inhibitors
• Mol File: 480-39-7.mol
• Article Data: 25

Chemical Properties

• Melting Point: 202 °C
• Boiling Point: 511.1 °C at 760 mmHg
• Flash Point: 199.3 °C
• Appearance: /
• Density: 1.386 g/cm³
• Vapor Pressure: 1.85E-11mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.50±0.40(Predicted)
• CAS DataBase Reference: PINOCEMBRIN(CAS DataBase Reference)
• NIST Chemistry Reference: PINOCEMBRIN(480-39-7)
• EPA Substance Registry System: PINOCEMBRIN(480-39-7)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 480-39-7(Hazardous Substances Data)

Usage

Description

Pinocembrin is a flavonoid that has been found in Eucalyptus, and has diverse biological activities. It induces apoptosis in, and inhibits the migration of, SKOV3 ovarian cancer cells when used at a concentration of 200 μM. Pinocembrin (5 mg/kg) reduces lesion volume, as well as brain microglial activation and production of IL-1β, IL-6, and TNF-α in a mouse model of collagenase-induced intracerebral hemorrhage (ICH). It prevents increases in plasma and kidney malondialdehyde (MDA) levels, glomeruli lobulation, mesangial expansion, and tubule vacuolization and occlusion, and it decreases hepatic cholesterol, triglyceride, and LDL levels in a rat model of diabetic nephropathy. Pinocembrin (20 and 50 mg/kg) reduces pulmonary edema, as well as neutrophil, lymphocyte, and macrophage infiltration in a mouse model of LPS-induced lung injury.

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 480-39-7 differently. You can refer to the following data:
1. Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bc l-2 ratio and by inhibiting the release of cytochrome c.
2. Pinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bcl-2 ratio and by inhibiting the release of cytochrome c.

InChI:InChI=1/C15H12O4/c16-10-6-12(17)11-8-13(18)15(19-14(11)7-10)9-4-2-1-3-5-9/h1-7,15-17H,8H2

Upstream product

• 480-39-7 pinocembrin 
• 120980-33-8 7-(benzyloxy)-5-hydroxyflavanone 
• 1159852-71-7 C₃₀H₂₇NO₃ 
• 108-73-6 3,5-dihydroxyphenol 
• 21947-71-7 cinnamic anhydride 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 102-92-1 cinnamoyl chloride 
• 102-92-1 Cinnamoyl chloride 
• 1036-72-2 5,7-dimethoxyflavone 
• 1775-97-9 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropenone 
• 621-82-9 Cinnamic acid 
• 7446-70-0 aluminium trichloride 
• 71-43-2 benzene 
• 145781-78-8 S-(2-acetamidoethyl) (E)-3-phenylprop-2-enethioate 

Downstream Products

• 88503-16-6 2'.4'.6'-triacetoxy-trans-chalcone 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 109592-60-1 7-acetylpinocembrine 
• 29646-98-8 pinostrobin Acetate 
• 140632-64-0 (+/-)-7-acetoxy-5-hydroxy-2-phenyl-chroman-4-one 
• 120980-33-8 7-(benzyloxy)-5-hydroxyflavanone 
• 88687-68-7 (+/-)-5,7-dihydroxy-2-phenyl-chroman-4-one-(2,4-dinitro-phenylhydrazone) 
• 75291-74-6 pinostrobin 
• 493-43-6 2-phenyl-chroman-5,7-diol 
• 111822-11-8 linderatone 
• 123357-16-4 (R)-5,7-Dihydroxy-8-((1R,6R)-6-isopropyl-3-methyl-cyclohex-2-enyl)-2-phenyl-chroman-4-one 
• 123297-92-7 neolinderatone 
• 123406-75-7 (R)-5,7-Dihydroxy-6,8-bis-((1R,6R)-6-isopropyl-3-methyl-cyclohex-2-enyl)-2-phenyl-chroman-4-one 
• 1036-72-2 5,7-dimethoxyflavone 

Relevant articles and documents

New flavanonglycoside from Glycyrrhiza glabra

A new flavanonglycoside pinocembroside, 2(S)-7-O-β-D-glucopyranosyl-5-hydroxyflavanone, was isolated from the aerial part of Glycyrrhiza glabra L. Its structure was determined using chemical transformations and spectral data.

Design, synthesis, and cholinesterase inhibition assay of liquiritigenin derivatives as anti-Alzheimer's activity

The marine environment is a rich resource for discovering functional materials, and seaweed is recognized for its potential use in biology and medicine. Liquiritigenin has been isolated and identified from Sargassum pallidum. To find new anti-Alzheimer's activity, we designed and synthesized thirty-two 7-prenyloxy-2,3-dihydroflavanone derivatives (3a-3p) and 5-hydroxy-7-prenyloxy-2,3-dihydro-flavanone derivatives (4a-4p) as cholinesterases inhibitors based on liquiritigenin as the lead compound. Inhibition screening against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) indicated that all synthesized compounds possessed potent AChE inhibitory activity and moderated to weak BuChE inhibitory activity in vitro. Kinetic studies demonstrated that compound 4o inhibited AChE via a dual binding site ability. In addition, all compounds displayed the radical scavenging effects. Finally, the molecular docking simulation of 4o in AChE active site displayed good agreement with the obtained the pharmacological results.

Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca

In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3′. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3′ positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.