D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-

Base Information

• Chemical Name: D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-
• CAS No.: 2753-30-2
• Molecular Formula: C₂₈H₃₄O₇
• Molecular Weight: 482.574
• European Community (EC) Number: 689-008-9
• Mol file: 2753-30-2.mol

Synonyms:gedunin

Chemical Property of D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-

Chemical Property:

• Vapor Pressure: 4.31E-14mmHg at 25°C
• Melting Point: 218 °C(Solv: methanol (67-56-1))
• Boiling Point: 594.3°Cat760mmHg
• Flash Point: 313.2°C
• PSA: 95.34000
• Density: 1.28g/cm³
• LogP: 4.56070
• Storage Temp.: Store at +4°C
• Solubility.: Chloroform (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 482.23045342
• Heavy Atom Count: 35
• Complexity: 1030

Purity/Quality:

99%, ^*data from raw suppliers

Gedunin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)(C)C
• Isomeric SMILES: CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1([C@]45[C@H](O4)C(=O)OC([C@@]5(CC3)C)C6=COC=C6)C)C
• Description: Gedunin is a natural inhibitor of the heat shock protein (Hsp90; Item Nos. 22734 | 22735) co-chaperone p23 that also inhibits Hsp90 expression in human teratocarcinomal NTERA-2 cells in vitro at 5 μg/ml. This tetranortriterpenoid, which is isolated from A. indica, binds to and blocks the chaperone activity of p23 to induce apoptosis in HeLa-PRB cells in vitro at a concentration of 20 μM. Gedunin inhibits breast cancer cell proliferation in vitro, with IC50 values of 8.84 and 3.22 μM in MCF-7 and SKBr-3 cells, respectively, and inhibits the growth of PANC-1 pancreatic cancer cells (IC50 = 25 μM) by targeting the sonic hedgehog pathway to induce apoptosis. It also exerts anti-inflammatory effects in vivo. In a mouse model of articular inflammation induced by zymosan , gedunin (0.05-0.5 mg/kg, i.p.) reduces edema formation and the production of inflammatory cytokines. Gedunin (0.5 mg/kg) also inhibits the pleural accumulation of eosinophils and activated T lymphocytes in an ovalbumin-sensitized mouse model of allergic inflammation when administered prior to ovalbumin rechallenge. It also targets the lipopolysaccharide binding site and thus blocks Toll-like receptor 4 (TLR4) signaling in macrophages in vitro at a concentration of 10 μM.
• Uses: Gedunin is a naturally occurring Hsp90 inhibitor. In vitro, Gedunin induces Hsp90-dependent client protein degradation and displays antiproliferative activity (IC50 values are 3.22, 8.84 and 16.8 μM in SKBr3, MCF-7 and CaCo-2 cancer cell lines respectively). Gedunin exhibits antimalarial activity against P. falciparum (IC50 values are 0.14 and 3.1 μM in parasite development and [3H]-hypoxanthine uptake assays respectively).

Technology Process of D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)-

There total 6 articles about D-Homo-24-nor-17-oxachola-1,20,22-triene-3,16-dione, 7-(acetyloxy)-14,15:21,23-diepoxy-4,4,8-trimethyl-, (5alpha,7alpha,13alpha,14beta,15beta,17aalpha)- 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: 76.0%

14,15-epoxyazadiradione (58525-91-0,18385-59-6) → gedunin (2753-30-2,23577-78-8)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1039/c3gc40193f

Reference yield:

7α-acetoxy-14β,15β-epoxy-gedunan-1-ene-3-O-β-D-glucopyranoside (106984-18-3) → gedunin (2753-30-2,23577-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.85 g / 7percent H₂SO₄ / ethanol / 1) reflux, 5 hr, 2) r.t., 24 hr

2: 310 mg / CrO₃, pyridine

With pyridine; chromium(VI) oxide; sulfuric acid; In ethanol;

Reference yield:

7α-acetoxy-3β-hydroxy-14β,15β-epoxy-gedunan-1-ene (106984-19-4) → gedunin (2753-30-2,23577-78-8)

Guidance literature:

With pyridine; chromium(VI) oxide;

upstream raw materials:

7α-acetoxy-3β-hydroxy-14β,15β-epoxy-gedunan-1-ene

7α-acetoxy-14β,15β-epoxy-gedunan-1-ene-3-O-β-D-glucopyranoside

14,15-epoxyazadiradione

acetic anhydride

Downstream raw materials:

7-epi-dihydrogedunin

(1S,3aS,41R,4a1S,5R,10aS,12aS)-8-(benzyloxyimino)-1-(furan-3-yl)-4a1,7,7,10a,12a-pentamethyl-3-oxo-1,3.3a,4a1,5,6,6a,7,8,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]oxireno[2,3-d]isochromen-5-yl acetate

3β-hydroxy-3-deoxo-7-epi-dihydrogedunin

3α-hydroxy-3-deoxo-7-epi-dihydrogedunin

Refernces

• 1、 Kehrli, Anne R. H.,Taylor, David A. H.,Niven, Margaret. "The Synthesis of a 1α,2α,3α-Triacetoxy Limonoid". . p. 2057 - 2065. Retrieved 2007/10/02.