280348
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:
Molecular Weight:
223.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
220-079-7
Beilstein/REAXYS Number:
1760958
MDL number:
Assay:
97%
InChI key
GTGTXZRPJHDASG-UHFFFAOYSA-N
InChI
1S/C8H15BrO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6H2,1H3,(H,10,11)
SMILES string
CCCCCCC(Br)C(O)=O
assay
97%
contains
Silver Wool as stabilizer
Quality Level
bp
140 °C/5 mmHg (lit.)
density
1.278 g/mL at 25 °C (lit.)
functional group
bromo, carboxylic acid
Related Categories
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.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Regulatory Information
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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)
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
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
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
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