Introduction：Basic information about Pinostrobin CAS 480-37-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Pinostrobin Basic information
| Product Name: | Pinostrobin |
| Synonyms: | 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;Pinostobin;Pistrobin;Pinostrobin,(S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4H-1-benzopyran-4-one;PINOCEMBRIN-7-METHYLETHER(RG)(PLEASE CALL);5-Hydroxy-7-methoxy-2-phenyl-chroman-4-one;5-Hydroxy-7-methoxyflavanone |
| CAS: | 480-37-5 |
| MF: | C16H14O4 |
| MW: | 270.28 |
| EINECS: | 207-548-1 |
| Product Categories: | Flavanones |
| Mol File: | 480-37-5.mol |
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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 |
Pinostrobin Preparation Products And Raw materials
| Raw materials | 4H-1-Benzopyran-4-one, 5,7-diMethoxy--->(+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE-->2'-HYDROXY-4',6'-DIMETHOXYACETOPHENONE-->Phenylboronic acid-->3,5-Dimethoxyphenol |
