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238422

Sigma-Aldrich

2-Bromohexadecanoic acid

~97%

Synonyme(s) :

2-Bromopalmitic acid

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About This Item

Formule linéaire :
CH3(CH2)13CH(Br)CO2H
Numéro CAS:
18263-25-7
Poids moléculaire :
335.32
Numéro Beilstein :
1726517
Numéro CE :
242-137-0
Numéro MDL:
MFCD00004215
Code UNSPSC :
12352203
ID de substance PubChem :
57648040
Nomenclature NACRES :
NA.77

Pureté

~97%

Niveau de qualité

100

Forme

solid

Chaîne SMILES 

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)

Clé InChI

DPRAYRYQQAXQPE-UHFFFAOYSA-N

Informations sur le gène

human ... PPARD(5467)

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Description générale

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

235.4 °F - closed cup

Point d'éclair (°C)

113 °C - closed cup

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Consulter la Bibliothèque de documents

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)
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
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
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.
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
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