Bongkrekic acid

Molecular Formula:

C28H38O7

CAS number:

11076-19-0

EU number:

Not on ECHA as of 12-2023

Fermentek product code:

BON

Source:

Pseudomonas gladioli

Brand/grade:

For research

Specifications

Appearance:

White to off white lyophilizate

Purity by HPLC:

≥95% ; refer to CoA for more data

Purity By TLC:

≥98% ; refer to CoA for more data

Solubility test:

Clear colorless solution at 1mg/ml of Water

Chemical identification

Names and identifiers:

Synonyms:

Bongkrekic Acid
BA
Flavotoxin A

Disambiguation: Regarding BA, Bongrekic acid, iso-Bongkrekic acid, Flavotoxin A, Toxiflavin.
Flavotoxin A is a Synonym of BA.
Bongkrekic acid (BA) and iso-Bongkrekic acid (iso-BA) are closely related compounds, sharing identic chemical formulas.
Toxiflavin which occurs together with BA and iso-BA is indeed a chemically unrelated compound.

Chemical names:

IUPAC:

(6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid

RTECS

JR1230000

Chemical name:

Bongkrekic acid

Description:

Bongkrekic acid is a respiratory toxin produced by Burkholderia gladioli (aka Pseudomonas marginata). Bongkrekic acid has a unique mechanism of toxicity among the mitochondrial toxins: it inhibits adenine nucleotide translocase (ANT) rather than the electron transport chain. It is a proven cause of mass deaths by contaminating certain Far-Eastern foods based on fermented coconut.

Molecular weight:

486.60

InChl Key:

SHCXABJSXUACKU-WUTQZGRKSA-N

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:

CC(C/C=C/CC/C=C/C=C\CC(/C(=C\C=C(/C)\C(=O)O)/C)OC)/C=C/C(=C\C(=O)O)/CC(=O)O

Further Information

Solubility ( literature ):

Solubility in Water: ~ 1 mg/ml
Solubility Notes: ~100 mg/ml in DMSO

Compound Classification:

Chemical classification:
Polyunsaturated tricarboxylic acid

Bioactivity:

Glutathione transferase inhibitor
ATP/ADP translocase inhibitor

Storage, handling:

Store in a freezer upon arrival, at -10°C to -25°C

Protect from light !

Open carefully.

Use the original container to store the product.

Keep the lid tightly closed.

Avoid exposing to strong direct light.

Other vendors may recommend higher temperatures for storage.

Applications:

Bongcrekic acid is an inhibitor of adenine nucleotide translocator, which inhibits apoptosis, and is thus an important tool for the mechanistic investigation of apoptosis.

Disclaimer:

For Research use only

Not for Human or Drug use

Not extracted from humans or animals

Refer to MSDS for further safety and handling instructions

Composition

Ingredient type:

Fermentek product

Supply related information

Supply related comments:

Shipped at ambient temperature

Shipped in PP / PE bottle.

Antib-29419000

Publications

J Med Toxicol. 2017 Jun; 13(2): 173–179.

Bongkrekic Acid—a Review of a Lesser-Known Mitochondrial Toxin (review)

Mehruba Anwar, Amelia Kasper, Alaina R. Steck, Joshua G. Schier

DOI:10.5109/1929661

Evergreen: joint journal of Novel Carbon Resource Sciences & Green Asia Strategy 2017-09

Bongkrekic Acid induces Selective Cytotoxicity in Tumor Cells, revealed by CCK-8
Kano Arihiro, Kamita Moses Kibunja, Iwasaki Takuma, Shindo Mitsuru

Published 2019
Chemistry, Medicine, Biochemistry and Biophysics Reports
Bongkrekic acid facilitates glycolysis in cultured cells and induces cell death under low glucose conditions
Arihiro Kano, Takuma Iwasaki, M. Shindo

Special Info

Available since:

2020

Other Fields

Title:

CAS ambiguity

Value:

# 60132-21-0 belongs to Isobongkrekic acid . http://www.molbase.com/en/cas-60132-21-0.html

Title:

oral LD50

Value:

oral LD50 of the purified Flavotoxin A in mice 3.16 mg/kg

Title:

More identity comments; Hu WJ et al; Biomed Environ Sci 2 (1): 65-71 (1989)

Value:

Therefore, Flavotoxin A and bongkrekic acid are the same organic chemical compound; the molecular formula is C28H38O7. The oral LD50 of the purified Flavotoxin A in mice was 3.16 mg/kg (1.53-6.15 mg/kg).

Title:

Deleted CAS Registry Numbers

Value:

11002-93-0, 12715-13-8, 32839-39-7

Title:

oral LD50

Value:

ANOTHER SOURCE: MOUSE LDL0=6.85 mg/kg PMID:6391376 source not recommended