Isobrucein A

Base Information

• Chemical Name: Isobrucein A
• CAS No.: 57629-50-2
• Molecular Formula: C26H34O11
• Molecular Weight: 522.5416
• Nikkaji Number: J40.237K
• Wikidata: Q27106962
• Mol file: 57629-50-2.mol

Synonyms:ISOBRUCEIN A;57629-50-2;CHEBI:5987;C08769;Q27106962;methyl (1beta,11beta,12alpha,15beta)-1,11,12-trihydroxy-15-[(3-methylbutanoyl)oxy]-2,16-dioxo-13,20-epoxypicras-3-en-21-oate;methyl (1R,2S,3R,6R,8S,12S,13S,14R,15R,16S,17S)-12,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbutanoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate

Chemical Property of Isobrucein A

Chemical Property:

• Vapor Pressure: 3.93E-23mmHg at 25°C
• Boiling Point: 707.5°Cat760mmHg
• Flash Point: 235.2°C
• Density: 1.43g/cm³
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 522.21011190
• Heavy Atom Count: 37
• Complexity: 1080

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C(C2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)OC)O)O)C)O
• Isomeric SMILES: CC1=CC(=O)[C@H]([C@]2([C@H]1C[C@@H]3[C@]45[C@@H]2[C@H]([C@@H]([C@]([C@@H]4[C@H](C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)OC)O)O)C)O

Technology Process of Isobrucein A

There total 5 articles about Isobrucein 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: 26.0%

isopentanoyl chloride (108-12-3) + C21H26O10 (190379-17-0) → isobrucein A (57629-50-2)

Guidance literature:

With pyridine; In chloroform; at 0 - 25 ℃; for 4h;

DOI:10.1248/cpb.45.675

Reference yield:

C26H36O11 (99133-01-4) → isobrucein A (57629-50-2)

Guidance literature:

With manganese(IV) oxide;

DOI:10.1248/cpb.32.4702

Reference yield:

yadanzioside H (95258-21-2) → isobrucein A (57629-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 15 mg / H2O / 336 h / 37 °C / β-glucosidase

2: 3 mg / MnO₂ / dimethylformamide / 6 h

With manganese(IV) oxide; water; In N,N-dimethyl-formamide;

DOI:10.1246/bcsj.58.2680

upstream raw materials:

C₂₆H₃₆O₁₁

isopentanoyl chloride

C₂₁H₂₆O₁₀

isobrucein B

Refernces

• 1、 Rahman, Shakila,Fukamiya, Narihiko,Ohno, Nobuhiro,Tokuda, Harukuni,Nishino, Hoyoku,Tagahara, Kiyoshi,Lee, Kuo-Hsiung,Okano, Masayoshi. "Inhibitory effects of quassinoid derivatives on Epstein-Barr virus early antigen activation". . p. 675 - 677. Retrieved 1997.
• 2、 Sakaki,Yoshimura,Ishibashi,et al.. "New quassinoid glycosides, yadanziosides A - H, from Brucea javanica". . p. 4702 - 4705. Retrieved 2007/10/02.