238422
2-Bromohexadecanoic acid
~97%, PPARδ agonist, solid
Synonym(s):
2-Bromopalmitic acid
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About This Item
Linear Formula:
CH3(CH2)13CH(Br)CO2H
CAS Number:
Molecular Weight:
335.32
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352203
EC Number:
242-137-0
MDL number:
Beilstein/REAXYS Number:
1726517
Product Name
2-Bromohexadecanoic acid, ~97%
assay
~97%
Quality Level
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)
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.
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Storage Class
11 - Combustible Solids
wgk
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
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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)
Abiy M Mohammed et al.
Biochemical pharmacology, 85(1), 109-114 (2012-10-25)
Phagocyte-like NADPH oxidase (Nox2) has been shown to play regulatory roles in the metabolic dysfunction of the islet β-cell under the duress of glucolipotoxic conditions and exposure to proinflammatory cytokines. However, the precise mechanisms underlying Nox2 activation by these stimuli
Aaron C Baldwin et al.
American journal of physiology. Endocrinology and metabolism, 302(11), E1390-E1398 (2012-03-23)
Exposure of insulin-producing cells to elevated levels of the free fatty acid (FFA) palmitate results in the loss of β-cell function and induction of apoptosis. The induction of endoplasmic reticulum (ER) stress is one mechanism proposed to be responsible for