BONGKREKIC ACID

BONGKREKIC ACID Structure
CAS No.
11076-19-0
Chemical Name:
BONGKREKIC ACID
Synonyms
edioicacid;bongkrekicaci;BONGKREKIC ACID;bongkrekic acid solution;Bongkrekic Acid (AS SOLUTION);(r-(r*,s*(e,z,z,e,e,z,e)))--trimethyl;Bongkrekic Acid Solution (1.0mg/mL in 0.01 M Tris buffer, pH 7.5);3-carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaen;2,4,8,10,14,18,20-docosaheptaenedioicacid,20-(carboxymethyl)-6-methoxy-2,5,17;(2E,4Z,6R,8Z,10E,14E,17S,18Z,20E)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
CBNumber:
CB4140241
Molecular Formula:
C28H38O7
Molecular Weight:
486.6
MOL File:
11076-19-0.mol
MSDS File:
SDS
Modify Date:
2024/7/2 8:55:07

BONGKREKIC ACID Properties

Melting point 50-60°
alpha D25 +162.5°
Boiling point 715.1±60.0 °C(Predicted)
Density 1.114±0.06 g/cm3(Predicted)
storage temp. -20°C
solubility Soluble in DMSO (up to 100 mg/ml) or in Water (up to 1 mg/ml).
form Lyophilized solid
pka 4.15±0.10(Predicted)
color Colorless to light yellow
Stability Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.

SAFETY

Risk and Safety Statements

WGK Germany  -
Toxicity LD50 i.v. in mice: 1.41 mg/kg (Lijmbach)

BONGKREKIC ACID price More Price(1)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) B6179 Bongkrekic acid solution from Pseudomonas cocovenenans, ≥95% (HPLC), ~1?mg/mL 11076-19-0 0.5MG ₹59678.23 2022-06-14 Buy
Product number Packaging Price Buy
B6179 0.5MG ₹59678.23 Buy

BONGKREKIC ACID Chemical Properties,Uses,Production

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.

Definition

ChEBI: A tricarboxylic acid that is docosa-2,4,8,10,14,18,20-heptaenedioic acid substituted at positions 2 ,5 and 17 by methyl groups, at positions 6 by a methoxy group and at position 20 by a carboxymethyl group.

Enzyme inhibitor

This toxic tricarboxylic acid (FWfree-acid = 486.61 g/mol; CAS 11076-19-0), produced Pseudomonas cocovenenans, is a potent competitive inhibitor of the mitochondrial ATP-ADP translocator, effectively blocking nucleotide binding to the carrier. The name is derived from bongkrek, a moldy coconut product produced in Indonesia. The toxin accumulates when P. cocovenenans outgrows the mold. Klingenberg et al. investigated bongkrekate binding to mitochondrial membrane to examine the reorienting site mechanism. The inferred mode of inhibition requires bongkrekate to bind to the single carrier site only from the inner face of the mitochondrial membrane (i.e., the matrix side)). They confirmed the pH-dependent accumulation of [3H]bongkrekate inside the mitochondria which superimposes onto the binding at carrier sites. By breaking the membrane with Lubrol or sonication, binding to the carrier sites could be titrated, and a Kd value of approximately 5 x 10–8 M was determined. The presence of ADP or ATP increases the amount of binding but does not alter the Kd. [35S]Atractylate is displaced by [3H]bongkrekate at a 1:1 molar ratio; this displacement is dependent on ADP concentration with the Km = 0.5 x 10–6 M. See also Atractyloside The isomer known as isobongkrekic acid, which has a cis-double bond at the dicarboxylic acid end of the molecule, has similar biological activity. Target(s): Adenine nucleotide translocator, ADP/ATP carrier; ATPase; bromelain, stem; papain; ficain, or ficin.

BONGKREKIC ACID Preparation Products And Raw materials

BONGKREKIC ACID Suppliers

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bongkrekic acid solution (2E,4Z,6R,8Z,10E,14E,17S,18Z,20E)-20-Carboxymethyl-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid BONGKREKIC ACID (r-(r*,s*(e,z,z,e,e,z,e)))--trimethyl 2,4,8,10,14,18,20-docosaheptaenedioicacid,20-(carboxymethyl)-6-methoxy-2,5,17 3-carboxymethyl-17-methoxy-6,18,21-trimethyldocosa-2,4,8,12,14,18,20-heptaen edioicacid bongkrekicaci 2,4,8,10,14,18,20-Docosaheptaenedioic acid, 20-(carboxymethyl)-6-methoxy-2,5,17-trimethyl-, (2E,4Z,6R,8Z,10E,14E,17S,18E,20Z)- Bongkrekic Acid Solution (1.0mg/mL in 0.01 M Tris buffer, pH 7.5) Bongkrekic Acid (AS SOLUTION) 11076-19-0 C28H38O7 BioChemical Apoptosis and Cell Cycle Cell Biology Apoptosis Inhibitors Cell Signaling and Neuroscience