Saikosaponin D

Base Information

• Chemical Name: Saikosaponin D
• CAS No.: 20874-52-6
• Molecular Formula: C42H68O13
• Molecular Weight: 780.994
• Hs Code.: 29389090
• European Community (EC) Number: 633-808-2
• UNII: UR635J3F00
• DSSTox Substance ID: DTXSID301317467
• Nikkaji Number: J221.226I
• Wikidata: Q27291219
• Metabolomics Workbench ID: 132813
• ChEMBL ID: CHEMBL3613719
• Mol file: 20874-52-6.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 D

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 256- 259oC
• 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.: Methanol (Slightly), 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:

98%,99%, ^*data from raw suppliers

Saikosaponin D ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

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
• Description: Saikosaponin D is a triterpene saponin found in Bupleurum that exhibits antioxidative, immunomodulatory, anti-fibrotic, anti-angiogenic, anticancer, and chemopreventive activities. Saikosaponin D increases activity of superoxide dismutase, catalase, and glutathione peroxidase and decreases activity of malondialdehyde in cellular models of oxidative damage. In other in vitro models, saikosaponin D increases secretion of IL-12, maturation of dendritic cells, and proliferation of lymphocytes. Saikosaponin D inhibits SERCA, increasing intracellular Ca2+ and inducing autophagy. In vivo, this compound decreases severity of fibrosis. In embryos, saikosaponin D decreases microvessel formation. Additionally, this compound decreases tumor formation in DEN-treated animal models and suppresses expression of CEBP-β and COX-2. Saikosaponin D also induces apoptosis and activation of caspases 3 and 7 in hepatocellular carcinoma cells. Saikosaponin D is a Glucocorticoid receptor agonist. It is a COX-2 and iNOS inhibitor.
• Uses: Saikosaponin d (SSd) is an important active component of Bupleurum scorzonerifolium Willd., a traditional Chinese medicinal herb. Saikosaponins such as Saikosaponin D are used to help analyse and resolve the activities of herbal medicines such as Sho-saiko-to. Saikosaponin D is an inhibitor of proliferation of human prostate cancer cells through arresting the cell cycle.

Technology Process of Saikosaponin D

There total 7 articles about Saikosaponin D 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:

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

Reference yield:

C56H80O20 → saikosaponin a (20736-09-8,20874-52-6,92137-96-7,92137-97-8)

Guidance literature:

Multi-step reaction with 2 steps

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

2: Na / aq. ethanol

With sodium hydroxide; sodium; In methanol; ethanol;

DOI:10.1039/c39860001417

upstream raw materials:

saikosaponin-a octaacetate

C₅₈H₈₄O₂₁

Downstream raw materials:

saikosaponin b₂

prosaikogenin G

Refernces

• 1、 Ishii,Nakamura,Seo,et al.. "Isolation, characterization, and nuclear magnetic resonance spectra of new saponins from the roots of Bupleurum falcatum L.". . p. 2367 - 2373. Retrieved 2007/10/02.