Raddeanin A

Base Information

• Chemical Name: Raddeanin A
• CAS No.: 89412-79-3
• Molecular Formula: C47H76O16
• Molecular Weight: 897.111
• Hs Code.: 29329990
• European Community (EC) Number: 683-257-7
• Nikkaji Number: J3.163.898D
• Mol file: 89412-79-3.mol

Synonyms:anemodeanin A;oleanolic acid 3-O-alpha-rhamnopyranosyl(1-2)-beta-glucopyranosyl(1-2)-alpha-arabinopyranoside

Chemical Property of Raddeanin A

Chemical Property:

• Melting Point: 242～244℃
• Boiling Point: 967.2 °C at 760 mmHg
• PKA: 4?+-.0.70(Predicted)
• Flash Point: 276.2 °C
• PSA: 254.52000
• Density: 1.36 g/cm³
• LogP: 2.37290
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 8
• Exact Mass: 896.51333633
• Heavy Atom Count: 63
• Complexity: 1720

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Raddeanin A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(COC3OC4CCC5(C(C4(C)C)CCC6(C5CC=C7C6(CCC8(C7CC(CC8)(C)C)C(=O)O)C)C)C)O)O)CO)O)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]([C@H](O[C@H]2O[C@@H]3[C@H]([C@H](CO[C@H]3O[C@H]4CC[C@]5([C@H](C4(C)C)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7CC(CC8)(C)C)C(=O)O)C)C)C)O)O)CO)O)O)O)O)O
• Uses: Raddeanin A is a triterpenoid saponin posessing anti-tumor activity, inhibiting proliferation and inducing apoptosis.

Technology Process of Raddeanin A

There total 3 articles about Raddeanin A 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: 91.8%

3-O-α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-α-L-arabinopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl(1->4)-β-D-glucopyranosyl(1->6)-β-D-glucopyranosyl(1->4)-α-L-rhamnopyranosyl(1->4)-β-D-glucopranosyl(1->6)-β-D-glucopyranoside → 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid (89412-79-3)

Guidance literature:

With ammonium hydroxide; at 100 ℃; for 5h;

DOI:10.1016/j.phytol.2012.01.007

Reference yield: 83.0%

benzyl oleanolate 3-O-α-L-rhamnopyranosyl-(1→2)-3″,4″,6″-tri-O-benzyl-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside → 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid (89412-79-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In methanol; at 20 ℃; for 24h; under 6000.6 Torr;

DOI:10.1248/cpb.c14-00138

Reference yield:

raddeanoside R8 (124961-61-1) → 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid (89412-79-3) + methyl α-L-rhamnosyl-(1->4)-O-β-D-glucopyranosyl-(1->6)-(α and β)-D-glucopyranoside (109606-00-0)

Guidance literature:

With 2,6-dimethylpyridine; lithium iodide; In methanol; for 16h; Heating;

DOI:10.1248/cpb.37.2445

upstream raw materials:

raddeanoside R₈

Refernces

• 1、 Li, Fu,Sun, Cui-Rong,Chen, Bin,Ding, Li-Sheng,Wang, Ming-Kui. "Triterpenoid saponins from Anemone raddeana". experimental part. p. 258 - 261. Retrieved 2012/07/03.