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280348

Sigma-Aldrich

2-Bromooctanoic acid

97%

Synonym(s):

2-Bromocaprylic acid

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About This Item

Linear Formula:
CH3(CH2)5CH(Br)COOH
CAS Number:
2623-82-7
Molecular Weight:
223.11
Beilstein:
1760958
EC Number:
220-079-7
MDL number:
MFCD00004219
UNSPSC Code:
12352100
PubChem Substance ID:
24856942
NACRES:
NA.22

Quality Level

200

Assay

97%

contains

Silver Wool as stabilizer

refractive index

n20/D 1.471 (lit.)

bp

140 °C/5 mmHg (lit.)

density

1.278 g/mL at 25 °C (lit.)

SMILES string

CCCCCCC(Br)C(O)=O

InChI

1S/C8H15BrO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6H2,1H3,(H,10,11)

InChI key

GTGTXZRPJHDASG-UHFFFAOYSA-N

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General description

2-Bromooctanoic acid is an effective substitute for the expensive (2,000 times) and cell-growth-inhibiting polyhydroxyalkanoic acid synthesis inhibitor, cerulenin. It blocks the formation of polyhydroxyalkanoic acid in Pseudomonas fluorescens BM07 without any influence on the cell growth when grown on fructose. It inhibits β-oxidation of fatty acids in perfused rat liver and in mitochondria isolated from rat liver.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Channeling of intermediates derived from medium-chain fatty acids and de novo-synthesized fatty acids to polyhydroxyalkanoic acid by 2-bromooctanoic acid in Pseudomonas fluorescens BM07.
LEE H-J, et al.
Journal of microbiology and biotechnology, 14(6), 1256-1266 (2004)
B M Raaka et al.
The Journal of biological chemistry, 254(14), 6755-6762 (1979-07-25)
Incubation of rat liver mitochondria with 10 microM DL-2-bromooctanoate causes complete and irreversible inactivation of 3-ketothiolase I (acyl-CoA:acetyl-CoA C-acyltransferase). Evidence is presented that mitochondria convert bromooctanoate to 2-bromo-3-ketooctanoyl-CoA, an alpha-haloketone which is probably the active form of the inhibitor. The
W E Roediger et al.
British journal of experimental pathology, 67(6), 773-782 (1986-12-01)
There is some evidence that failure of fatty acid or beta-oxidation in the epithelium of the colonic mucosa is associated with the development of ulcerative colitis. We tested the hypothesis that inhibition of fatty acid oxidation in the colonic mucosa
N Mayorek et al.
The Journal of biological chemistry, 260(11), 6528-6532 (1985-06-10)
Triacylglycerol synthesis in cultured rat hepatocytes was inhibited by 2-bromooctanoate with a concomitant accumulation of diacylglycerols. 2-Bromooctanoate inhibition could be ascribed to its thioesterification by medium chain fatty acyl-CoA synthase (Raaka, B.M., and Lowenstein, J.M. (1979) J. Biol. Chem. 254
N Mayorek et al.
European journal of biochemistry, 182(2), 395-400 (1989-06-15)
The limiting role of diacylglycerol acyltransferase with respect to triacylglycerol synthesis in cultured rat hepatocytes was evaluated by following the inhibition of the overall synthetic flux by 2-bromooctanoate acting as an inhibitor of the diacylglycerol acyltransferase step. The flux-control coefficient
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