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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:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

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)
Caglar Gök et al.
Cell reports, 31(10), 107697-107697 (2020-06-11)
The transmembrane sodium-calcium (Na-Ca) exchanger 1 (NCX1) regulates cytoplasmic Ca levels by facilitating electrogenic exchange of Ca for Na. Palmitoylation, the only reversible post-translational modification known to modulate NCX1 activity, controls NCX1 inactivation. Here, we show that palmitoylation of NCX1
Eric Cortada et al.
Journal of cell science, 134(6) (2021-02-20)
The voltage-gated sodium channel is critical for cardiomyocyte function. It consists of a protein complex comprising a pore-forming α subunit and associated β subunits. In polarized Madin-Darby canine kidney cells, we show evidence by acyl-biotin exchange that β2 is S-acylated
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
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.
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