Bruceolide

Base Information

• Chemical Name: Bruceolide
• CAS No.: 25514-28-7
• Molecular Formula: C₂₁H₂₆O₁₀
• Molecular Weight: 438.431
• DSSTox Substance ID: DTXSID30948401
• Nikkaji Number: J20.267C
• Wikipedia: Bruceolide
• Wikidata: Q27133978
• Metabolomics Workbench ID: 123448
• ChEMBL ID: CHEMBL140588
• Mol file: 25514-28-7.mol

Synonyms:BRUCEOLIDE;25514-28-7;CHEBI:65529;NSC 238185;Methyl (11beta,12alpha,15beta)-13,20-epoxy-3,11,12,15-tetrahydroxy-2,16-dioxopicras-3-en-21-oate;methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3,10,15,16-tetrahydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate;Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12,15-tetrahydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta)-;C21-H26-O10;CHEMBL140588;DTXSID30948401;Q27133978;methyl (11beta,12alpha,15beta)-3,11,12,15-tetrahydroxy-2,16-dioxo-13,20-epoxypicras-3-en-21-oate;Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12,15-tetrahydroxy-2,16-dioxo-, methyl ester,(11beta,12alpha,15beta)-

Chemical Property of Bruceolide

Chemical Property:

• Vapor Pressure: 7.78E-23mmHg at 25°C
• Boiling Point: 702.8°Cat760mmHg
• PKA: 8.86±0.70(Predicted)
• Flash Point: 248°C
• PSA: 159.82000
• Density: 1.58g/cm³
• LogP: -1.00010
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 2
• Exact Mass: 438.15259702
• Heavy Atom Count: 31
• Complexity: 927

Purity/Quality:

99%min ^*data from raw 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)O)(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)O)(OC5)C(=O)OC)O)O)C)O

Technology Process of Bruceolide

There total 5 articles about Bruceolide 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: 86.0%

deacetylyadanzioside F → Bruceolid (25514-28-7)

Guidance literature:

With acetate buffer; celluase from Aspergillus niger;

DOI:10.1016/S0960-894X(98)00045-6

Reference yield: 44.0%

Brusatol (14907-98-3) → Bruceolid (25514-28-7)

Guidance literature:

With potassium hydroxide; In methanol; for 8.5h; Heating;

DOI:10.1016/S0968-0896(97)00095-3

Reference yield:

bruceoside A (63306-30-9,84607-61-4) → Bruceolid (25514-28-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 10percent H₂SO₄ / methanol / 6 h / Heating

2: 44 percent / 0.5 N KOH / methanol / 8.5 h / Heating

With potassium hydroxide; sulfuric acid; In methanol;

DOI:10.1016/S0968-0896(97)00095-3

upstream raw materials:

Brusatol

bruceoside A

Downstream raw materials:

Brucein B

Refernces

• 1、 Ohno, Nobuhiro,Fukamiya, Narihiko,Okano, Masayoshi,Tagahara, Kiyoshi,Lee, Kuo-Hsiung. "Synthesis of cytotoxic fluorinated quassinoids". . p. 1489 - 1495. Retrieved 2007/10/03.