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Merck
CN

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:
2623-82-7
Molecular Weight:
223.11
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24856942
EC Number:
220-079-7
Beilstein/REAXYS Number:
1760958
MDL number:
MFCD00004219

Key Documents

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Product Name

2-Bromooctanoic acid, 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

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

Quality Level

200

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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

signalword

Danger

hcodes

H314

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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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)
Karen M Tobin et al.
FEMS microbiology letters, 253(1), 111-118 (2005-11-02)
A number of Pseudomonas strains accumulated polyhdroxyalkanoate (PHA) from a variety of aromatic hydrocarbons. In many strains the level of PHA accumulation was dependent on the side chain length of the phenylalkanoic acid provided for growth. 4 of the 8
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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