Rhamnazin 3-rutinoside

Base Information

• Chemical Name: Rhamnazin 3-rutinoside
• CAS No.: 20188-85-6
• Molecular Formula: C29H34 O16
• Molecular Weight: 638.579
• DSSTox Substance ID: DTXSID50942249
• Wikidata: Q82919220
• Mol file: 20188-85-6.mol

Synonyms:Rhamnazin 3-O-rutinoside;Rhamnazin 3-rutinoside;5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one;4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-;64527-08-8;DTXSID50942249;CHEBI:168233;AKOS032948987;E80728;4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-;4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-;5-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside

Chemical Property of Rhamnazin 3-rutinoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 946°Cat760mmHg
• Flash Point: 308°C
• PSA: 247.43000
• Density: 1.66g/cm³
• LogP: -1.08110
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 638.18468499
• Heavy Atom Count: 45
• Complexity: 1060

Purity/Quality:

98%Min ^*data from raw suppliers

Ombuoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
• Uses: Ombuoside is a flavonoid that has been reported to have antimicrobial activity against several strains of Gram-positive and Gram-negative bacteria and the yeast Candida albicans.

Technology Process of Rhamnazin 3-rutinoside

There total 2 articles about Rhamnazin 3-rutinoside 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: 33.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + rutin (153-18-4) → rhamnetin 3-O-rutinoside + 7,4′-di-O-methylquercetin-3-O-beta-rutinoside (20188-85-6) + 2-(3,4-Dimethoxy-phenyl)-5-hydroxy-7-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-2-yloxy]-chromen-4-one

Guidance literature:

In methanol; diethyl ether; at 20 ℃; for 1h;

DOI:10.1248/cpb.50.788

Reference yield:

dimethyl sulfate (77-78-1) + rutin (153-18-4) → rhamnetin 3-O-rutinoside + quercetin-3'-O-methyl-3-O-α-L-rhamnopyranosyl(1->6)-β-D-glucopyranoside + 7,4′-di-O-methylquercetin-3-O-beta-rutinoside (20188-85-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 65 ℃; for 6h;

DOI:10.1016/j.bmc.2014.04.053

Reference yield:

7,4′-di-O-methylquercetin-3-O-beta-rutinoside (20188-85-6) → β-D-glucose (492-61-5) + L-rhamnose (6014-42-2) + ombuin (529-40-8)

Guidance literature:

With sulfuric acid; In water; at 100 ℃; for 1h; Product distribution;

DOI:10.1016/S0031-9422(00)83550-5

upstream raw materials:

diazomethane

rutin

dimethyl sulfate

Downstream raw materials:

β-D-glucose

L-rhamnose

ombuin

5-acetoxy-2-(3-acetoxy-4-methoxy-phenyl)-7-methoxy-3-[O²,O³,O⁴-triacetyl-O⁶-(tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranosyloxy]-chromen-4-one

Refernces

• 1、 Matsuda, Hisashi,Morikawa, Toshio,Toguchida, Iwao,Yoshikawa, Masayuki. "Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity". . p. 788 - 795. Retrieved 2007/10/03.