Fortunellin

Base Information

• Chemical Name: Fortunellin
• CAS No.: 20633-93-6
• Molecular Formula: C28H32O14
• Molecular Weight: 592.554
• DSSTox Substance ID: DTXSID00861996
• Nikkaji Number: J702.438J
• Wikidata: Q63409698
• Mol file: 20633-93-6.mol

Synonyms:acacetin-7-O-neohesperidoside;fortunellin

Chemical Property of Fortunellin

Chemical Property:

• Vapor Pressure: 6.89E-34mmHg at 25°C
• Melting Point: 193-198oC
• Boiling Point: 888.7°Cat760mmHg
• PKA: 6.10±0.40(Predicted)
• Flash Point: 293.4°C
• PSA: 217.97000
• Density: 1.62g/cm³
• LogP: -0.79530
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 7
• Exact Mass: 592.17920569
• Heavy Atom Count: 42
• Complexity: 955

Purity/Quality:

99%+, ^*data from raw suppliers

Acacetin-7-neohesperidoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=C3)OC(=CC4=O)C5=CC=C(C=C5)OC)O)CO)O)O)O)O)O
• Description: Fortunellin is a potential anti-inflammation agent in inflammatory diseases, it targets miR-374a, which is a negative regulator of phosphatase and tensin homolog (PTEN). Fortunellin protects against high fructose-induced diabetic heart injury in mice by suppressing inflammation and oxidative stress via AMPK/Nrf-2 pathway regulation.
• Biological Functions: Fortunellin (acacetin 7-O-neohesperidoside) is a citrus flavonoid isolated from kumquat fruit. Kumquat extract has attracted much attention recently for its beneficial effects on human health, which include antitumor, antioxidant and anti-inflammatory characteristics . The beneficial effects of flavonoids on IBD have been confirmed in many studies. However, although fortunellin is the main flavonoid in kumquat, there is a lack of information on its alleviation of IBD.

Technology Process of Fortunellin

There total 1 articles about Fortunellin 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: 88.0%

5-acetoxy-7-[hexa-O-acetyl-(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]-4'-methoxyflavone → 5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone (20633-93-6)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h;

DOI:10.1016/j.molcatb.2016.03.001

Reference yield: 87.0%

5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone (20633-93-6) → 5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one (480-44-4)

Guidance literature:

With ethanol; sulfuric acid; for 2h; Reflux;

DOI:10.1016/j.molcatb.2016.03.001

Reference yield:

5-hydroxy-4'-methoxy-7-[(2-O-α-L-rhamnopyranosyl-β-D-glucopyranosyl)oxy]flavone (20633-93-6) → acacetin diacetate (5892-39-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid; ethanol / 2 h / Reflux

2: pyridine

With pyridine; ethanol; sulfuric acid;

DOI:10.1016/j.molcatb.2016.03.001

Downstream raw materials:

5,7-dihydroxy-2-(4'-methoxyphenyl)-4H-1-benzopyran-4-one

acacetin diacetate

Refernces