Pinostrobin

Base Information

• Chemical Name: Pinostrobin
• CAS No.: 480-37-5
• Molecular Formula: C16H14O4
• Molecular Weight: 270.285
• Hs Code.: 2932999099
• European Community (EC) Number: 207-548-1
• Nikkaji Number: J2.950.372I
• Wikidata: Q27165805
• Mol file: 480-37-5.mol

Synonyms:5-hydroxy-7-methoxy-2-phenyl-2,3-dihydro-4H-chromen-4-one;5-hydroxy-7-methoxyflavanone;pinostrobin

Chemical Property of Pinostrobin

Chemical Property:

• Vapor Pressure: 2.03E-10mmHg at 25°C
• Melting Point: 100 °C
• Refractive Index: 1.612
• Boiling Point: 494.9 °C at 760 mmHg
• PKA: 7.40±0.40(Predicted)
• Flash Point: 188.8 °C
• PSA: 55.76000
• Density: 1.284 g/cm³
• LogP: 3.10730
• Storage Temp.: 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 350

Purity/Quality:

99%, ^*data from raw suppliers

Pinostrombin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=CC=C3)O
• Isomeric SMILES: COC1=CC(=C2C(=O)C[C@@H](OC2=C1)C3=CC=CC=C3)O
• 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).

Technology Process of Pinostrobin

There total 13 articles about Pinostrobin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

Pinocembrin dimethyl ether (1036-72-2,36052-66-1,89395-30-2) → pinostrobin (480-37-5)

Guidance literature:

With aluminum (III) chloride; In acetonitrile; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ol2004148

Reference yield:

2-hydroxy-4,6-dimethoxyacetophenone (90-24-4) → pinostrobin (480-37-5)

Guidance literature:

Multi-step reaction with 4 steps

1: o-xylene / 4 h / Reflux; Inert atmosphere

2: sulfuric acid; water / 2 h / Reflux; Inert atmosphere

3: [Rh(OH)(cod)]2; (S)-MeO-F₁₂-BIPHEP / water; toluene / 3 h / 60 °C / Inert atmosphere

4: aluminum (III) chloride / acetonitrile / 3 h / Reflux; Inert atmosphere

With aluminum (III) chloride; [Rh(OH)(cod)]2; sulfuric acid; (S)-MeO-F₁₂-BIPHEP; water; In o-xylene; water; toluene; acetonitrile;

DOI:10.1021/ol2004148

Reference yield:

3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one (187877-87-8) → pinostrobin (480-37-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid; water / 2 h / Reflux; Inert atmosphere

2: [Rh(OH)(cod)]2; (S)-MeO-F₁₂-BIPHEP / water; toluene / 3 h / 60 °C / Inert atmosphere

3: aluminum (III) chloride / acetonitrile / 3 h / Reflux; Inert atmosphere

With aluminum (III) chloride; [Rh(OH)(cod)]2; sulfuric acid; (S)-MeO-F₁₂-BIPHEP; water; In water; toluene; acetonitrile;

DOI:10.1021/ol2004148

upstream raw materials:

pinostrobin 5-O-β-D-glucopyranoside

diazomethane

Pinocembrin dimethyl ether

3,5-dimethoxyphenol

Downstream raw materials:

pinostrobin oxime

Refernces

• 1、 Hodgetts, Kevin J.. "Inter- and intramolecular Mitsunobu reaction based approaches to 2-substituted chromans and chroman-4-ones". . p. 6860 - 6870. Retrieved 2007/10/03.
• 2、 Geibel, Martin,Feucht, Walter. "FLAVONOID 5-GLUCOSIDES FROM PRUNUS CERASUS BARK AND THEIR CHARACTERISTIC WEAK GLYCOSIDIC BONDING". . p. 1519 - 1521. Retrieved 2007/10/02.