Saikosaponin A

Base Information

• Chemical Name: Saikosaponin A
• CAS No.: 20736-09-8
• Molecular Formula: C42H68O13
• Molecular Weight: 780.994
• Hs Code.: 29389090
• European Community (EC) Number: 633-799-5
• UNII: 09O6CAG7JV
• DSSTox Substance ID: DTXSID00942951
• Nikkaji Number: J221.227G
• Wikipedia: Sho-saiko-to
• Wikidata: Q7499688
• ChEMBL ID: CHEMBL3542194
• Mol file: 20736-09-8.mol

Synonyms:saikosaponin A;saikosaponin B;saikosaponin B1;saikosaponin B2;saikosaponin B3;saikosaponin B4;saikosaponin C;saikosaponin D;saikosaponin K;saikosaponin L;saikosaponins

Chemical Property of Saikosaponin A

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 225 - 235oC
• Refractive Index: 1.616
• Boiling Point: 893.675 °C at 760 mmHg
• PKA: 12.83±0.70(Predicted)
• Flash Point: 494.277 °C
• PSA: 207.99000
• Density: 1.36 g/cm³
• LogP: 1.77690
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Pyridine (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 6
• Exact Mass: 780.46599222
• Heavy Atom Count: 55
• Complexity: 1490

Purity/Quality:

95%-98% ^*data from raw suppliers

Saikosaponin A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC56C4(CC(C7(C5CC(CC7)(C)C)CO6)O)C)C)C)O)OC8C(C(C(C(O8)CO)O)O)O)O
• Isomeric SMILES: C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=C[C@@]56[C@]4(C[C@@H]([C@@]7([C@H]5CC(CC7)(C)C)CO6)O)C)C)C)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O
• Uses: Saikosaponin A was shown to exhibit anti-inflammatory activities by suppressing activation of NF-kB signaling pathway.

Technology Process of Saikosaponin A

There total 8 articles about Saikosaponin 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: 100.0%

C42H66O13 → saikosaponin a (20736-09-8,20874-52-6,92137-96-7,92137-97-8)

Guidance literature:

With sodium; In ethanol;

DOI:10.1039/c39860001417

Reference yield:

2-O-acetylsaikosaponin a (102934-42-9) → saikosaponin A (20736-09-8)

Guidance literature:

With potassium hydroxide; In methanol; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.34.1158

Reference yield:

C56H82O20 → saikosaponin a (20736-09-8,20874-52-6,92137-96-7,92137-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1: CrO₃, pyridine

2: 2percent NaOH / methanol / 1 h / Heating

3: Na / aq. ethanol

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium; In methanol; ethanol;

DOI:10.1039/c39860001417

upstream raw materials:

saikosaponin-a octaacetate

C₅₈H₈₄O₂₁

2-O-acetylsaikosaponin a

Downstream raw materials:

3-O-β-D-glucopyranosyl-(1->3)-β-D-fucopyranosyl 3β,16β,23,28-tetrahydroxyolean-9(11),12(13)-diene

prosaikogenin F

saikosaponin B₁

Refernces

• 1、 Ogihara, Yukio,Nose, Mitsuhiko. "Novel Cleavage of the Glycosidic Bond of Saponins in Alcoholic Alkali Metal Solution containing a Trace of Water". . p. 1417. Retrieved 2007/10/02.