PINOCEMBRIN Chemical Properties

Melting point:

202 °C

Boiling point:

511.1±50.0 °C(Predicted)

Density 

1.386±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

Soluble in ethanol and methan

form 

powder

pka

7.50±0.40(Predicted)

color 

White

LogP

3.225 (est)

EPA Substance Registry System

4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)- (480-39-7)

Safety Information

Safety Statements 

24/25

HS Code 

29329990

PINOCEMBRIN Usage And Synthesis

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

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.

Definition

ChEBI: Pinocembrin is a dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea. It has a role as an antioxidant, an antineoplastic agent, a vasodilator agent, a neuroprotective agent and a metabolite. It is a dihydroxyflavanone and a (2S)-flavan-4-one.

References

[1] AZHAR RASUL. Pinocembrin: a novel natural compound with versatile pharmacological and biological activities.[J]. BioMed Research International, 2013: 379850. DOI: 10.1155/2013/379850
[2] JUN GAO . Pinocembrin inhibits the proliferation and migration and promotes the apoptosis of ovarian cancer cells through down-regulating the mRNA levels of N-cadherin and GABAB receptor[J]. Biomedicine & Pharmacotherapy, 2019, 120: Article 109505. DOI: 10.1016/j.biopha.2019.109505
[3] XI LAN. Pinocembrin protects hemorrhagic brain primarily by inhibiting toll-like receptor 4 and reducing M1 phenotype microglia[J]. Brain, Behavior, and Immunity, 2017, 61: Pages 326-339. DOI: 10.1016/j.bbi.2016.12.012
[4] JESSICA GRANADOS-PINEDA. Effect of Pinocembrin Isolated from Mexican Brown Propolis on Diabetic Nephropathy.[J]. Molecules, 2018, 23 4. DOI: 10.3390/molecules23040852
[5] LANAN WASSY SOROMOU . In vitro and in vivo protection provided by pinocembrin against lipopolysaccharide-induced inflammatory responses[J]. International immunopharmacology, 2012, 14 1: Pages 66-74. DOI: 10.1016/j.intimp.2012.06.009

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