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Sigma-Aldrich

2-Bromohexadecanoic acid

~97%

Synonym(s):

2-Bromopalmitic acid

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About This Item

Linear Formula:
CH3(CH2)13CH(Br)CO2H
CAS Number:
18263-25-7
Molecular Weight:
335.32
Beilstein/REAXYS Number:
1726517
EC Number:
242-137-0
MDL number:
MFCD00004215
UNSPSC Code:
12352203
PubChem Substance ID:
57648040
NACRES:
NA.77

assay

~97%

form

solid

SMILES string

CCCCCCCCCCCCCCC(Br)C(O)=O

InChI

1S/C16H31BrO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15H,2-14H2,1H3,(H,18,19)

InChI key

DPRAYRYQQAXQPE-UHFFFAOYSA-N

Gene Information

human ... PPARD(5467)

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General description

PPARδ (peroxisome proliferator-activated receptor, delta isoform) acts as a transcription factor for gene expression as well as playing a role in lipid metabolism regulation; activity of this receptor is ligand-regulated. 2-Bromohexadecanoic acid is a metabolically stable analoge of the fatty acid palmitic acid that has been shown to be a natural ligand for the PPARδ receptor. 2-Bromohexadecanoic acid has also been used in studies of fatty acid oxidation, palmitoylation, and glucose uptake.

Biochem/physiol Actions

2-Bromohexadecanoic acid is a PPARδ agonist. It has also been shown to inhibit fatty acid oxidation, inhibit DHHC-mediated palmitoylation, and promote glucose uptake in rat cardiac cells and the insulin-sensitive murine fibroblast line A31-IS.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Joel Berger et al.
Annual review of medicine, 53, 409-435 (2002-01-31)
The peroxisome proliferator-activated receptors (PPARs) are a group of three nuclear receptor isoforms, PPAR gamma, PPAR alpha, and PPAR delta, encoded by different genes. PPARs are ligand-regulated transcription factors that control gene expression by binding to specific response elements (PPREs)
Benjamin C Jennings et al.
Journal of lipid research, 50(2), 233-242 (2008-10-02)
Pharmacologic approaches to studying palmitoylation are limited by the lack of specific inhibitors. Recently, screens have revealed five chemical classes of small molecules that inhibit cellular processes associated with palmitoylation (Ducker, C. E., L. K. Griffel, R. A. Smith, S.
Priyanka Tripathi et al.
Journal of lipid research, 62, 100021-100021 (2021-01-01)
Microtubules are polymers composed of αβ-tubulin subunits that provide structure to cells and play a crucial role in in the development and function of neuronal processes and cilia, microtubule-driven extensions of the plasma membrane that have sensory (primary cilia) or
Kenji Hayata et al.
Journal of pharmacological sciences, 108(3), 348-354 (2008-11-15)
To obtain compounds that promote glucose uptake in muscle cells, the novel cell lines A31-IS derived from Balb/c 3T3 A31 and C2C12-IS from mouse myoblast C2C12 were established. In both cell lines, glucose consumption was induced by insulin and suppressed
Wei Yuan et al.
Proceedings of the National Academy of Sciences of the United States of America, 118(13) (2021-03-24)
The homeostasis of protein palmitoylation and depalmitoylation is essential for proper physiological functions in various tissues, in particular the central nervous system (CNS). The dysfunction of PPT1 (PPT1-KI, infantile neuronal ceroid lipofuscinosis [INCL] mouse model), which catalyze the depalmitoylation process
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