Pinostrobin Chemical Properties

Melting point:

100°C

Boiling point:

494.9±45.0 °C(Predicted)

Density 

1.284±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

DMF: 20 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml; DMSO: 12 mg/ml

form 

A crystalline solid

pka

7.40±0.40(Predicted)

color 

White to yellow

InChI

InChI=1S/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/t14-/m0/s1

InChIKey

ORJDDOBAOGKRJV-AWEZNQCLSA-N

SMILES

[C@H]1(C2=CC=CC=C2)OC2=CC(OC)=CC(O)=C2C(=O)C1

LogP

3.591 (est)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Pinostrobin Usage And Synthesis

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).

Uses

Pinostrombin is a useful research chemical that can be used for chemical fingerprinting, isolating, and characterizing of polyphenol compounds. It can also be used as a potential compound for TMPRSS2 inhibition for Covid-19 therapy.

Definition

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

References

[1] NEERAJ K. PATEL  Kamlesh K B  Gaurav Jaiswal. A review on biological sources, chemistry and pharmacological activities of pinostrobin[J]. Natural Product Research, 2016, 30 18: Pages 2017-2027. DOI: 10.1080/14786419.2015.1107556
[2] JED W. FAHEY  Katherine K S. Pinostrobin from Honey and Thai Ginger (Boesenbergia pandurata): A Potent Flavonoid Inducer of Mammalian Phase 2 Chemoprotective and Antioxidant Enzymes[J]. Journal of Agricultural and Food Chemistry, 2002, 50 25: 7472-7476. DOI: 10.1021/jf025692k
[3] NEERAJ K. PATEL  Kamlesh K B. Pinostrobin and Cajanus lactone isolated from Cajanus cajan (L.) leaves inhibits TNF-α and IL-1β production: In vitro and in vivo experimentation[J]. Phytomedicine, 2014, 21 7: Pages 946-953. DOI: 10.1016/j.phymed.2014.02.011
[4] J.S. ASHIDI . Ethnobotanical survey and cytotoxicity testing of plants of South-western Nigeria used to treat cancer, with isolation of cytotoxic constituents from Cajanus cajan Millsp. leaves[J]. Journal of ethnopharmacology, 2010, 128 2: Pages 501-512. DOI: 10.1016/j.jep.2010.01.009

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