KAEMPFEROL 3-O-GLUCORHAMNOSIDE

Base Information

• Chemical Name: KAEMPFEROL 3-O-GLUCORHAMNOSIDE
• CAS No.: 482-39-3
• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.384
• UNII: 5M86W1YH7O
• DSSTox Substance ID: DTXSID50197459
• Nikkaji Number: J12.243B
• Wikipedia: Afzelin
• Wikidata: Q3334749
• ChEMBL ID: CHEMBL240528
• Mol file: 482-39-3.mol

Synonyms:5,7-Dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl 6-deoxy-α-L-mannopyranoside;

Chemical Property of KAEMPFEROL 3-O-GLUCORHAMNOSIDE

Chemical Property:

• Vapor Pressure: 1.19E-24mmHg at 25°C
• Melting Point: 172-174 °C (decomp)(Solv: water (7732-18-5))
• Refractive Index: 1.748
• Boiling Point: 765.6 °C at 760 mmHg
• PKA: 6.20±0.40(Predicted)
• Flash Point: 272.3 °C
• PSA: 170.05000
• Density: 1.7 g/cm³
• LogP: 0.78310
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 432.10564683
• Heavy Atom Count: 31
• Complexity: 702

Purity/Quality:

99%, ^*data from raw suppliers

Kaempferin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
• Uses: Kaempferol 3-O-α-L-Rhamnoside is found in Cornus macrophylla and has shown to have antibacterial activity against Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals.

Technology Process of KAEMPFEROL 3-O-GLUCORHAMNOSIDE

There total 23 articles about KAEMPFEROL 3-O-GLUCORHAMNOSIDE 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: 80.0%

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one (916069-04-0) → kaempferol 3-rhamnoside (482-39-3,22334-39-0,28978-08-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; at 20 ℃; for 3h;

DOI:10.1021/ol062076r

Reference yield: 80.0%

4',5,7-tri-O-benzyl-kaempferol 3-O-(2''-O-benzyl-α-L-rhamnopyranoside) (942942-49-6) → kaempferol 3-rhamnoside (482-39-3,22334-39-0,28978-08-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In tetrahydrofuran; methanol; for 1h;

DOI:10.1016/j.bmc.2007.03.087

Reference yield: 41.0%

kaempferol (520-18-3) + C15H24N2O17P2 → kaempferol 3-rhamnoside (482-39-3,22334-39-0,28978-08-7)

Guidance literature:

With recombinant rhamnosyl transferase from Epimedium pseudowushanense; UDP-rhamnose synthase from Epimedium pseudowushanense; nicotinamide adenine dinucleotide; NADPH; In dimethyl sulfoxide; at 30 ℃; for 12h; pH=7.4; regioselective reaction; Enzymatic reaction;

DOI:10.1039/c7ob02763j

upstream raw materials:

Kaempferol-3-O-(3,4-O-diacetyl-α-L-rhamnopyranoside)

Kaempferol-3-O-(2,4-di-O-acetyl-alpha-L-rhamnopyranoside)

kaempferitrin

5,7-bis(benzyloxy)-2-(4-(benzyloxy)phenyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Downstream raw materials:

kaempferol

Peracetylated-SL₀₁₀₁

L-rhamnose

kaempferol 5,7,4'-trimethyl ether

Refernces

• 1、 Wang, Mengyue,Xing, Shihua,Luu, Thithanhthuy,Fan, Min,Li, Xiaobo. "The Gastrointestinal Tract Metabolism and Pharmacological Activities of Grosvenorine, a Major and Characteristic Flavonoid in the Fruits of Siraitia grosvenorii". . p. 1652 - 1664. Retrieved 2015/11/24.
• 2、 Alaniya,Kavtaradze, N. Sh.,Skhirtladze,Pizza,Piacente. "Flavonol glycoside from humulus lupulus". body text. p. 641 - 642. Retrieved 2011/02/23.