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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.)

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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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
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)
M Danis et al.
The Journal of pharmacology and experimental therapeutics, 219(2), 383-388 (1981-11-01)
Mixed-function oxidation of p-nitroanisole in isolated perfused livers from fasted rats was studied in the presence and absence of 2-bromooctanoate, an inhibitor of the beta-oxidation of acyl CoA compounds. These experiments were designed to test the hypothesis that reducing equivalents
Umi S Ramli et al.
The FEBS journal, 272(22), 5764-5770 (2005-11-11)
We applied metabolic control analysis to the Kennedy pathway for triacylglycerol formation in tissue cultures from the important oil crops, olive (Olea europaea L.) and oil palm (Elaeis guineensis Jacq.). When microsomal fractions were incubated at 30 degrees C rather
R Hertz et al.
The Biochemical journal, 245(2), 387-392 (1987-07-15)
1. The induction of peroxisomal beta-oxidation activities by bezafibrate in cultured rat hepatocytes and in the rat in vivo was prevented by inhibitors of carnitine acyltransferase, e.g. 2-bromopalmitate, 2-[5-(4-chlorophenyl)pentyl]oxirane-2-carboxylate or 2-tetradecylglycidic acid. 2. The prevention of peroxisomal proliferation by carnitine
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