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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

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.)

functional group

bromo
carboxylic acid

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

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Certificates of Analysis (COA)

Lot/Batch Number
0001452977
1452977V
1452977
013317/1
06829AH

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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
Aisling R Hume et al.
Journal of bacteriology, 191(24), 7554-7565 (2009-10-13)
A fatty acyl coenzyme A synthetase (FadD) from Pseudomonas putida CA-3 is capable of activating a wide range of phenylalkanoic and alkanoic acids. It exhibits the highest rates of reaction and catalytic efficiency with long-chain aromatic and aliphatic substrates. FadD
J G Conway et al.
Cancer research, 47(18), 4795-4800 (1987-09-15)
The diffusion of H2O2 into the cytoplasm from peroxisomes during high rates of peroxisomal beta oxidation of fatty acids was studied in perfused livers from rats treated with the hepatocarcinogenic peroxisome proliferator, nafenopin. Efflux of oxidized glutathione (GSSG) into the
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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