| Identification | Back Directory | [Name]
Pinostrobin | [CAS]
480-37-5 | [Synonyms]
Pistrobin
Pinostobin
PINOSTROBIN
Pinostrombin
5-Hydroxy-7-methoxyflavanone
PINOCEMBRIN-7-METHYLETHER(RG)(PLEASE CALL)
5-Hydroxy-7-methoxy-2-phenyl-chroman-4-one
(S)-2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone
2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one
2-Phenyl-5-hydroxy-7-methoxy-2,3-dihydro-4H-1-benzopyran-4-one
(S)-2,3-DIHYDRO-5-HYDROXY-7-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE
(2S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-7-methoxy-2-phenyl-, (2S)-
Pinostrobin,(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one | [EINECS(EC#)]
207-548-1 | [Molecular Formula]
C16H14O4 | [MDL Number]
MFCD06858342 | [MOL File]
480-37-5.mol | [Molecular Weight]
270.28 |
| Chemical Properties | Back Directory | [Melting point ]
100°C | [Boiling point ]
494.9±45.0 °C(Predicted) | [density ]
1.284±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,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) |
| Hazard Information | Back Directory | [Description]
Pinostrobin is a flavonoid with diverse biological activities, including antioxidant, anti-inflammatory, and anticancer properties.1 It induces quinone reductase (QR) in murine hepatoma cells with a QR doubling concentration of 500 nM.2 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).3 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).4 | [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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