Catharticin

Base Information

• Chemical Name: Catharticin
• CAS No.: 39723-40-5
• Deprecated CAS: 71241-96-8,39723-41-6
• Molecular Formula: C34H42 O19
• Molecular Weight: 754.696
• DSSTox Substance ID: DTXSID50960327
• Nikkaji Number: J1.226.330I
• Wikidata: Q82941478
• Mol file: 39723-40-5.mol

Synonyms:Catharticin;39723-40-5;Alaternin (glycoside);Rhamnocitrin 3-O-beta-D-rhamninoside;3-(((2S,3R,4S,5R,6R)-6-((((2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one;4H-1-Benzopyran-4-one, 3-((O-6-deoxy-alpha-L-mannopyranosyl-(1-3)-O-6-deoxy-alpha-L-mannopyranosyl-(1-6)-beta-D-galactopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-;3-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxychromen-4-one;DTXSID50960327;C34H42O19;AKOS040761472;3-[[6-O-(3-O-alpha-L-Rhamnopyranosyl-alpha-L-rhamnopyranosyl)-beta-D-galactopyranosyl]oxy]-4',5-dihydroxy-7-methoxyflavone;5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-3-yl 6-deoxyhexopyranosyl-(1->3)-6-deoxyhexopyranosyl-(1->6)hexopyranoside

Chemical Property of Catharticin

Chemical Property:

• Melting Point: 185-189 °C(Solv: methanol (67-56-1))
• Boiling Point: 1061.4°Cat760mmHg
• PKA: 6.04±0.40(Predicted)
• Flash Point: 332.4°C
• PSA: 297.12000
• Density: 1.68g/cm³
• LogP: -2.23790
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 9
• Exact Mass: 754.23202911
• Heavy Atom Count: 53
• Complexity: 1280

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCC3C(C(C(C(O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@H]([C@@H]2O)OC[C@@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)OC4=C(OC5=CC(=CC(=C5C4=O)O)OC)C6=CC=C(C=C6)O)O)O)O)C)O)O)O)O

Technology Process of Catharticin

There total 6 articles about Catharticin 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:

3,5,7-Triacetoxy-4'-benzyloxy-flavon (30782-33-3) → kaempferol-7-O-methyl-3-O-α-L-rhamnopyranosyl(1<*>3)-O-α-L-rhamnopyranosyl(1<*>6)-O-β-D-galactopyranoside (39723-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / 1) Dimethylsulfat, K₂CO₃, 2) H₂O / acetone / Heating; 1) 30 h; 2) 15 min

2: 29 percent / Sikkon, Ag₂CO₃ / various solvent(s) / 6 h / Ambient temperature

3: Pd/C / ethyl acetate / 3 h

4: NaOCH₃ / methanol / Ambient temperature

With Sikkon; water; sodium methylate; potassium carbonate; dimethyl sulfate; silver carbonate; palladium on activated charcoal; In methanol; ethyl acetate; acetone;

DOI:10.1016/0040-4020(82)85113-2

Reference yield:

1,2,3,4-tetra-O-acetyl-6-O-<2,4,-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-D-galactopyranose (68398-79-8) → kaempferol-7-O-methyl-3-O-α-L-rhamnopyranosyl(1<*>3)-O-α-L-rhamnopyranosyl(1<*>6)-O-β-D-galactopyranoside (39723-40-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / 40percent HBr/Eisessigloesung / CH₂Cl₂ / 1.5 h / 0 °C

2: 29 percent / Sikkon, Ag₂CO₃ / various solvent(s) / 6 h / Ambient temperature

3: Pd/C / ethyl acetate / 3 h

4: NaOCH₃ / methanol / Ambient temperature

With Sikkon; hydrogen bromide; sodium methylate; acetic acid; silver carbonate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/0040-4020(82)85113-2

Reference yield:

4'-Benzyloxy-5-hydroxy-7-methoxy-flavon-3-O-octa-O-acetyl--β-D-galaktopyranosid (83170-25-6) → kaempferol-7-O-methyl-3-O-α-L-rhamnopyranosyl(1<*>3)-O-α-L-rhamnopyranosyl(1<*>6)-O-β-D-galactopyranoside (39723-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd/C / ethyl acetate / 3 h

2: NaOCH₃ / methanol / Ambient temperature

With sodium methylate; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/0040-4020(82)85113-2

upstream raw materials:

4',5-Dihydroxy-7-methoxy-flavon-3-O-octa-O-acetyl--β-D-galaktopyranosid

3,5,7-Triacetoxy-4'-benzyloxy-flavon

1,2,3,4-tetra-O-acetyl-6-O-<2,4,-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl>-D-galactopyranose

4'-Benzyloxy-5-hydroxy-7-methoxy-flavon-3-O-octa-O-acetyl--β-D-galaktopyranosid

Refernces