Orobol

Base Information

• Chemical Name: Orobol
• CAS No.: 480-23-9
• Molecular Formula: C15H10O6
• Molecular Weight: 286.241
• UNII: LU8UZM1T51
• ChEMBL ID: CHEMBL241609
• DSSTox Substance ID: DTXSID20197380
• Metabolomics Workbench ID: 22388
• Nikkaji Number: J12.354D
• NSC Number: 678114
• Wikidata: Q7103718
• Wikipedia: Orobol
• Mol file: 480-23-9.mol

Synonyms:3-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one;isoluteolin;orobol

Chemical Property of Orobol

Chemical Property:

• Melting Point: 270 °C
• Boiling Point: 616.1 °C at 760 mmHg
• PKA: 6.37±0.20(Predicted)
• Flash Point: 239.5 °C
• PSA: 111.13000
• Density: 1.654 g/cm³
• LogP: 2.28240
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 286.04773803
• Heavy Atom Count: 21
• Complexity: 447

Purity/Quality:

99%, ^*data from raw suppliers

Orobol 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O)O

Technology Process of Orobol

There total 22 articles about Orobol 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: 70.0%

3-(3,4-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one (53084-11-0) → orobol (480-23-9)

Guidance literature:

With pyridine hydrochloride; at 150 ℃; Inert atmosphere;

DOI:10.1016/j.bioorg.2021.105022

Reference yield: 10.0%

3-(3',4'-dihydroxyphenyl)-5,7-dimethoxy-4H-chromen-4-one → orobol (480-23-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 60 ℃; for 18h;

DOI:10.1021/acschemneuro.9b00232

Reference yield:

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on (446-72-0) → orobol (480-23-9)

Guidance literature:

With NADPH; cytochrome P₄₅₀; In water; at 37 ℃; pH=7.4; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1021/tx9802320

upstream raw materials:

3-(3,4-dimethoxyphenyl)-5,7-dimethoxychromen-4-one

8-C-β-D-glucopyranosylorobol

6,8-di-C-β-D-glucopyranosyl-3',4',5,7-tetrahydroxyisoflavone

3',4',5,7-tetrahydroxyisoflavone β-D-glucopyranoside

Downstream raw materials:

3',5,7-trihydroxy-4'-methoxyisoflavone

3'-O-methylorobol

Refernces

• 1、 Nam, Geewoo,Ji, Yonghwan,Lee, Hyuck Jin,Kang, Juhye,Yi, Yelim,Kim, Mingeun,Lin, Yuxi,Lee, Young-Ho,Lim, Mi Hee. "Orobol: An Isoflavone Exhibiting Regulatory Multifunctionality against Four Pathological Features of Alzheimer's Disease". . p. 3386 - 3390. Retrieved 2019.
• 2、 Roberts-Kirchhoff, Elizabeth S.,Crowley, Jan R.,Hollenberg, Paul F.,Kim, Hyesook. "Metabolism of genistein by rat and human cytochrome P450s". . p. 610 - 616. Retrieved 1999.
• 3、 Do, Ji Min,Gee, Min Sung,Inn, Kyung-Soo,Kim, Jong-Ho,Kim, Nam Kwon,Kim, Nam-Jung,Lee, Hyun Woo,Lee, Jong Kil,Seo, Min-Duk,Seong, Ji Hye,Son, Seung Hwan,Yoo, Hyung-Seok,Yoo, Ji-Na. "Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation". . . Retrieved 2021/07/01.
• 4、 Chiang, Chien-Min,Chang, Yu-Jhe,Wu, Jiumn-Yih,Chang, Te-Sheng. "Production and anti-melanoma activity of methoxyisoflavones from the biotransformation of genistein by two recombinant Escherichia coli strains". . . Retrieved 2017/01/24.