Bongkrekic acid

Base Information

• Chemical Name: Bongkrekic acid
• CAS No.: 11076-19-0
• Deprecated CAS: 11002-93-0,12715-13-8,32839-39-7
• Molecular Formula: C28H38 O7
• Molecular Weight: 486.606
• UNII: L7V4I673D2
• DSSTox Substance ID: DTXSID00894840
• Wikipedia: Bongkrek_acid
• Wikidata: Q4941885
• Metabolomics Workbench ID: 101708
• Mol file: 11076-19-0.mol

Synonyms:Bongkrekate;Bongkrekic Acid;Flavotoxin A

Chemical Property of Bongkrekic acid

Chemical Property:

• Melting Point: 50-60°
• Boiling Point: 715.1°Cat760mmHg
• PKA: 4.15±0.10(Predicted)
• Flash Point: 231°C
• PSA: 121.13000
• Density: 1.114g/cm³
• LogP: 5.88560
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 100 mg/ml) or in Water (up to 1 mg/ml).
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 17
• Exact Mass: 486.26175355
• Heavy Atom Count: 35
• Complexity: 898

Purity/Quality:

99% ^*data from raw suppliers

BongkrekicAcidSolution(1.0mg/mLin0.01MTrisbuffer,pH7.5) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC=CCCC=CC=CCC(C(=CC=C(C)C(=O)O)C)OC)C=CC(=CC(=O)O)CC(=O)O
• Isomeric SMILES: C[C@@H](C/C=C/CC/C=C/C=C\C[C@H](/C(=C\C=C(/C)\C(=O)O)/C)OC)/C=C/C(=C\C(=O)O)/CC(=O)O
• Description: Bongkrekic acid (11076-19-0) is a p potent inhibitory ligand of the mitochondrial adenine nucleotide translocase (ANT).1?Inhibits mitochondrial permeability transition pore opening.2,3?Delivery of bongkrekic acid to the mitochondria prevents apoptosis in HeLa cells.4
• Uses: Bongkrekic acid solution has been used as an adenine nucleotide translocator (ANT) inhibitor to find out a different approach for the inhibition of oxidative phosphorylation in intact T98G cells. It has also been used as an inhibitor of the permeabilization transition pore complex (PTPC) pore and a tool to explore the role of PTPC in induction of apoptosis.

Technology Process of Bongkrekic acid

There total 101 articles about Bongkrekic acid 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: 92.0%

(6R,17S)-bis(methoxymethyl) 20-(2-hydroxyethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioate → bongkrekic acid (11076-19-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

DOI:10.1002/chem.201501304

Reference yield: 83.0%

(Z)-3-[(1E,3S,5E,9E,11Z,14R,15Z,17E)-19-tert-butoxy-14-methoxy-3,15,18-trimethyl-19-oxononadeca-1,5,9,11,15,17-hexaenyl]pent-2-enedioic acid (1196458-46-4) → bongkrekic acid (11076-19-0)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1055/s-0029-1216928

Reference yield: 65.0%

(2E,4Z,8Z,10E,14E)-(6R,17S)-17-(4-Carboxymethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-6-methoxy-2,5-dimethyl-octadeca-2,4,8,10,14-pentaenoic acid (88304-12-5,88335-55-1) → bongkrekic acid (11076-19-0)

Guidance literature:

With potassium methanolate; In tetrahydrofuran; methanol; at 0 ℃; for 0.0833333h;

DOI:10.1021/ja00314a056

upstream raw materials:

(2E,4Z,8Z,10E,14E)-(6R,17S)-17-(4-Carboxymethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-6-methoxy-2,5-dimethyl-octadeca-2,4,8,10,14-pentaenoic acid

(2E,4Z,8Z,10E,14E,18E,20Z)-(6R,17S)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyl-docosa-2,4,8,10,14,18,20-heptaenedioic acid 1-tert-butyl ester 22-(tert-butyl-diphenyl-silanyloxymethyl) ester

(R)-5-((Z)-4-Hydroxy-but-2-enyl)-4-methyl-5H-furan-2-one

(R)-5-((2Z,4E)-6-Bromo-hexa-2,4-dienyl)-4-methyl-5H-furan-2-one

Refernces

• 1、 Corey, E. J.,Tramontano, Alfonso. "Total Synthesis of Bongkrekic Acid". . p. 462 - 463. Retrieved 1984.
• 2、 Francais, Antoine,Leyva-Perez, Antonio,Etxebarria-Jardi, Gorka,Pena, Javier,Ley, Steven V.. "Total synthesis of iso- and bongkrekic acids: Natural antibiotics displaying potent antiapoptotic properties". . p. 329 - 343. Retrieved 2011/03/21.
• 3、 Kanematsu, Makoto,Shindo, Mitsuru,Yoshida, Masahiro,Shishido, Kozo. "Total synthesis of bongkrekic acid via sequential suzuki-miyaura coupling reactions". experimental part. p. 2893 - 2904. Retrieved 2010/03/03.