Chryseriol

Base Information

• Chemical Name: Chryseriol
• CAS No.: 491-71-4
• Molecular Formula: C16H12O6
• Molecular Weight: 300.268
• European Community (EC) Number: 207-742-6
• UNII: Q813145M20
• ChEMBL ID: CHEMBL214321
• DSSTox Substance ID: DTXSID60197687
• Metabolomics Workbench ID: 23882
• Nikkaji Number: J90.397C
• NSC Number: 732318
• Pharos Ligand ID: R16J1UKNNT2F
• Wikidata: Q2967432
• Wikipedia: Chrysoeriol
• Mol file: 491-71-4.mol

Synonyms:5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one;8-chrysoeriol;chryseriol;chrysoeriol

Chemical Property of Chryseriol

Chemical Property:

• Vapor Pressure: 8.61E-14mmHg at 25°C
• Melting Point: >300°C (dec.)
• Refractive Index: 1.697
• Boiling Point: 574.3 °C at 760 mmHg
• PKA: 6.49±0.40(Predicted)
• Flash Point: 219.4 °C
• PSA: 100.13000
• Density: 1.512 g/cm³
• LogP: 2.58540
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated and Sonicated)
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 300.06338810
• Heavy Atom Count: 22
• Complexity: 462

Purity/Quality:

≥98% ^*data from raw suppliers

Chrysoeriol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O
• Uses: A methoxyflavonoid that selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. A metabolite of Luteolin (L475000). Chrysoeriol is a methoxyflavonoid that selectively inhibits the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. A metabolite of Luteolin (L475000).

Technology Process of Chryseriol

There total 40 articles about Chryseriol 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: 98.0%

3,5-dihydroxyphenol (108-73-6) + ethyl 3-(4-hydroxy-3-methoxyphenyl)-3-oxopropanoate (56222-44-7) → chrysoeriol (491-71-4)

Guidance literature:

In dimethyl sulfoxide; at 140 - 150 ℃; for 12h; Concentration;

Reference yield: 90.0%

3'-methoxy-4',5,7-tri[(2-methoxyethoxy)methoxy]flavone (1456788-20-7) → chrysoeriol (491-71-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.ejmech.2013.06.019

Reference yield: 86.0%

C37H30O6 → chrysoeriol (491-71-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; methanol; at 20 ℃; for 24h;

DOI:10.3390/molecules26103033

upstream raw materials:

2-[4-(benzyloxy)-3-methoxyphenyl]-5,7-dihydroxy-4H-chromen-4-one

(+/-)-homoeriodictyol

7,4′-dihydroxy-5,3′-dimethoxyflavone

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

Downstream raw materials:

7-acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-5-hydroxy-chromen-4-one

chrysoeriol tri-O-acetate

5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide

6-prenylchrysoeriol

Refernces

• 1、 Kattaev,Nikonov. "-". . . Retrieved 1975.
• 2、 Grisebach,Bilhuber. "On the biosynthesis of apigenin and chrysoeriol in parsley". . p. 746 - 751. Retrieved 1967.
• 3、 Ali, Bakhat,Imran, Muhammad,Hussain, Riaz,Ahmed, Zaheer,Malik, Abdul. "Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy". . p. 159 - 163. Retrieved 2010.
• 4、 Choe, Jung-Won,Heo, Hee-Young,Jung, Se-Hui,Kim, Jaehyun,Lee, Kooyeon. "Anti‐melanogenic properties of velutin and its analogs?". . . Retrieved 2021/06/03.
• 5、 Liu, Xiaojuan,Wang, Yue,Chen, Yezhi,Xu, Shuting,Gong, Qin,Zhao, Chenning,Cao, Jinping,Sun, Chongde. "Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products". . . Retrieved 2020/02/25.