Gardenin B

Base Information

• Chemical Name: Gardenin B
• CAS No.: 2798-20-1
• Molecular Formula: C19H18 O7
• Molecular Weight: 358.348
• NSC Number: 618926,79093
• UNII: 313E89KN5E
• DSSTox Substance ID: DTXSID10182260
• Nikkaji Number: J94.492K
• Wikidata: Q27148750
• Metabolomics Workbench ID: 24534
• ChEMBL ID: CHEMBL226512
• Mol file: 2798-20-1.mol

Synonyms:5-demethyltangeretin;gardenin B

Chemical Property of Gardenin B

Chemical Property:

• Vapor Pressure: 3.8E-14mmHg at 25°C
• Melting Point: 180-181oC
• Boiling Point: 582°C at 760 mmHg
• PKA: 6.83±0.40(Predicted)
• Flash Point: 210.8°C
• PSA: 87.36000
• Density: 1.309±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.20000
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 358.10525291
• Heavy Atom Count: 26
• Complexity: 526

Purity/Quality:

95%-98% ^*data from raw suppliers

Gardenin B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2=CC(=O)C3=C(C(=C(C(=C3O2)OC)OC)OC)O

Technology Process of Gardenin B

There total 19 articles about Gardenin B 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: 100.0%

5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone (2798-22-3) + dimethyl sulfate (77-78-1) → gardenin B (2798-20-1)

Guidance literature:

With potassium carbonate; In acetone; for 1h; Heating;

DOI:10.1016/j.tet.2004.01.023

Reference yield: 44.6%

xanthomicrol (16545-23-6) + dimethyl sulfate (77-78-1) → gardenin B (2798-20-1)

Guidance literature:

With potassium carbonate; In dichloromethane; acetone; for 4h; Reflux;

DOI:10.1021/np500671v

Reference yield: 31.8%

xanthomicrol (16545-23-6) + dimethyl sulfate (77-78-1) → gardenin B (2798-20-1) + tangeritin (481-53-8)

Guidance literature:

With potassium carbonate; In dichloromethane; acetone; for 4h; Reflux;

DOI:10.1021/np500671v

upstream raw materials:

5,8-dihydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)-4-benzopyrone

dimethyl sulfate

2'-hydroxy-4,4',6'-trimethoxychalcone

1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)propenone

Downstream raw materials:

tangeritin

Refernces

• 1、 Su, Liang,Jin, Zhizhong,Liu, Kexiong,Wang, Qiuan. "Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity". . p. 100 - 105. Retrieved 2022/03/27.
• 2、 Nguyen, Van-Son,Li, Wei,Li, Yue,Wang, Qiuan. "Synthesis of Citrus polymethoxyflavonoids and their antiproliferative activities on Hela cells". . p. 1585 - 1592. Retrieved 2017/06/05.