Bruceine A

Base Information

• Chemical Name: Bruceine A
• CAS No.: 25514-31-2
• Molecular Formula: C₂₆H₃₄O₁₁
• Molecular Weight: 522.549
• NSC Number: 310616
• DSSTox Substance ID: DTXSID901318520
• Nikkaji Number: J20.264I
• Wikidata: Q104397412
• Metabolomics Workbench ID: 129464
• ChEMBL ID: CHEMBL250451
• Mol file: 25514-31-2.mol

Synonyms:bruceine A;bruceine A, (1beta,11beta,12alpha,15beta)-isomer;isobruceine A

Chemical Property of Bruceine A

Chemical Property:

• Vapor Pressure: 1.85E-23mmHg at 25°C
• Boiling Point: 712.6°C at 760 mmHg
• PKA: 8.81±0.70(Predicted)
• Flash Point: 237.1°C
• Density: 1.43g/cm³
• Solubility.: insoluble in EtOH; insoluble in H2O; ≥5.23 mg/mL in DMSO with gentle warming
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 522.21011190
• Heavy Atom Count: 37
• Complexity: 1100

Purity/Quality:

≥98% ^*data from raw suppliers

BruceantinA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)CC2(C1CC3C45C2C(C(C(C4C(C(=O)O3)OC(=O)CC(C)C)(OC5)C(=O)OC)O)O)C)O
• Isomeric SMILES: CC1=C(C(=O)C[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 Bruceine A

There total 4 articles about Bruceine 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: 37.6%

methanol (67-56-1) + bruceoside E (167782-23-2) → bruceine A (25514-31-2)

Guidance literature:

With toluene-4-sulfonic acid; for 20h; Heating;

DOI:10.1248/cpb.48.876

Reference yield:

yadanzioside B (106387-01-3) → brucein A (25514-31-2)

Guidance literature:

With sulfuric acid; In methanol; water; hydrolysis;

DOI:10.1248/cpb.32.4702

Reference yield:

yadanzioside A (95258-15-4) → brucein A (25514-31-2)

Guidance literature:

With β-glucosidase; at 37 ℃;

DOI:10.1248/cpb.32.4702

upstream raw materials:

yadanzioside B

yadanzioside A

methanol

bruceoside E

Downstream raw materials:

2-hydroxy-2-deoxotetrahydrobrusatol lactol

tetrahydrobrusatol

Refernces

• 1、 Tamura, Sadaaki,Fukamiya, Narihiko,Mou, Xiao-Yang,Mukainaka, Teruo,Tokuda, Harukuni,Nishino, Hoyoku,Tagahara, Kiyoshi,Koike, Kazuo,Lee, Kuo-Hsiung,Okano, Masayoshi. "Conversion of quassinoids for enhancement of inhibitory effect against Epstein-Barr virus early antigen activation. Introduction of lipophilic side chain and esterification of diosphenol". . p. 876 - 878. Retrieved 2007/10/03.
• 2、 Sakaki,Yoshimura,Ishibashi,et al.. "New quassinoid glycosides, yadanziosides A - H, from Brucea javanica". . p. 4702 - 4705. Retrieved 2007/10/02.