[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

Base Information

• Chemical Name: [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate
• CAS No.: 465-16-7
• Molecular Formula: C₃₂H₄₈O₉
• Molecular Weight: 576.728
• European Community (EC) Number: 207-361-5
• NSC Number: 692219,95089
• Wikipedia: Oleandrin
• Wikidata: Q105130969
• Mol file: 465-16-7.mol

Synonyms:NSC692219;559-83-1;[(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate;465-16-7;NSC95089;NSC-95089;Card-20(22)-enolide,6-dideoxy-3-O-methyl-.alpha.-L-arabino-hexopyranosyl)oxy]-14-hydroxy-, (3.beta.,5.beta.,16.beta.)-

Chemical Property of [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 250°C
• Refractive Index: 1.567
• Boiling Point: 693.669oC at 760 mmHg
• PKA: 13.55±0.70(Predicted)
• Flash Point: 217.166oC
• PSA: 120.75000
• Density: 1.261g/cm3
• LogP: 3.68100
• Storage Temp.: -20°C Freezer
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 576.32983310
• Heavy Atom Count: 41
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

Oleandrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-33-23/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CC1C(C(CC(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CC(C5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
• Isomeric SMILES: CC1C(C(CC(O1)O[C@H]2CC[C@]3([C@@H](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(C[C@@H]([C@@H]5C6=CC(=O)OC6)OC(=O)C)O)C)C)OC)O
• Uses: Cardiotonic; diuretic

Technology Process of [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate

There total 1 articles about [(3S,5R,8R,9S,10S,13R,14S,16S,17R)-14-hydroxy-3-(5-hydroxy-4-methoxy-6-methyloxan-2-yl)oxy-10,13-dimethyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] acetate 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:

→ 3β-O-(β-D-sarmentosyl)-16β-acetoxy-14-hydroxy-5β,14β-card-20(22)-enolide (465-16-7,465-17-8,508-22-5,559-83-1,31087-94-2,144300-17-4,53177-88-1)

Guidance literature:

With enzyme-substance from seed of adenium multiflorum;

DOI:10.1002/hlca.19500330431

Reference yield: 25.0%

oleandrin (465-16-7,465-17-8,508-22-5,559-83-1,31087-94-2,144300-17-4,53177-88-1) → gitoxigenin (545-26-6)

Guidance literature:

With trifluoroacetic acid; In butan-1-ol; at 200 ℃; for 1.5h;

DOI:10.3390/molecules26103030

Reference yield:

oleandrin (465-16-7,465-17-8,508-22-5,559-83-1,31087-94-2,144300-17-4,53177-88-1) → oleandrigenin (465-15-6)

Guidance literature:

With hydrogenchloride; water; In ethanol; for 2h; Heating;

DOI:10.1007/BF01372612

Downstream raw materials:

oleandrigenin

4′-α-oleandrin

gitoxigenin