Gancaonin O

Base Information

• Chemical Name: Gancaonin O
• CAS No.: 129145-53-5
• Molecular Formula: C20H18 O6
• Molecular Weight: 354.359
• ChEMBL ID: CHEMBL1915459
• DSSTox Substance ID: DTXSID101128143
• Metabolomics Workbench ID: 23811
• Nikkaji Number: J990.678I
• Wikidata: Q104911271
• Mol file: 129145-53-5.mol

Synonyms:Gancaonin O;CHEMBL1915459;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-;2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one;SCHEMBL4836863;CHEBI:175547;DTXSID101128143;BDBM50358101;LMPK12110726;AKOS030553579;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI

Chemical Property of Gancaonin O

Chemical Property:

• Vapor Pressure: 7.86E-17mmHg at 25°C
• Boiling Point: 637.2°C at 760 mmHg
• Flash Point: 228.2°C
• Density: 1.388g/cm³
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 354.11033829
• Heavy Atom Count: 26
• Complexity: 593

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCC1=C(C2=C(C=C1O)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)C

Technology Process of Gancaonin O

There total 6 articles about Gancaonin O 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:

C28H34O10 → 2-[3,4-dihydroxyphenyl]-5,7-dihydroxy-6-[3-methylbut-2-enyl]chromone (129145-53-5)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; methanol; at 50 ℃; for 6h;

DOI:10.1016/j.ejmech.2011.10.006

Reference yield:

dimethylallyl diphosphate (358-72-5) + 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on (491-70-3) → 2-[3,4-dihydroxyphenyl]-5,7-dihydroxy-6-[3-methylbut-2-enyl]chromone (129145-53-5)

Guidance literature:

With magnesium chloride; In aq. buffer; at 30 ℃; for 12h;

DOI:10.1002/cbic.201402160

Reference yield:

3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one (1351279-85-0) → 2-[3,4-dihydroxyphenyl]-5,7-dihydroxy-6-[3-methylbut-2-enyl]chromone (129145-53-5)

Guidance literature:

Multi-step reaction with 3 steps

1: water; sodium acetate / ethanol / 24 h / Reflux

2: pyridine; iodine / 6 h / 90 °C

3: hydrogenchloride; water / tetrahydrofuran; methanol / 6 h / 50 °C

With pyridine; hydrogenchloride; water; iodine; sodium acetate; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/j.ejmech.2011.10.006

upstream raw materials:

3-(3,4-bis(methoxymethoxy)phenyl)-1-(6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl)prop-2-en-1-one

3,4-bis-methoxymethoxy-benzaldehyde

1-[6-hydroxy-2,4-bis(methoxymethoxy)-3-(3-methylbut-2-en-1-yl)phenyl]ethanone

3',4',5,7-tetramethoxymethoxy-6-(3,3-dimethylallyl)flavanone

Refernces

• 1、 Dong, Xiaowu,Zhou, Xinglu,Jing, Hui,Chen, Jianzhong,Liu, Tao,Yang, Bo,He, Qiaojun,Hu, Yongzhou. "Pharmacophore identification, virtual screening and biological evaluation of prenylated flavonoids derivatives as PKB/Akt1 inhibitors". experimental part. p. 5949 - 5958. Retrieved 2012/02/01.