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21604

Sigma-Aldrich

2-Bromohexadecanoic acid

≥99.0% (GC)

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
Beilstein/REAXYS Number:
1726517
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

≥99.0% (GC)

form

solid

mp

52-54 °C

solubility

methanol: soluble 1 g/10 mL, clear, colorless
chloroform: soluble
ethanol: soluble
water: insoluble

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

2-Bromohexadecanoic acid, also known as 2-Bromopalmitic acid, is a long chain 2-haloalkanoic halogenated fatty acid that is commonly used as a building block in various organic reaction such as 2′-(2-bromohexadecanoyl)-docetaxel synthesis.

Application

<ul>
<li><strong>Chemo-immunotherapy Applications:</strong> 2-Bromohexadecanoic acid has been utilized to create bioactive fatty acid analog-derived hybrid nanoparticles for chemo-immunotherapy against carcinoma, demonstrating potential in cancer treatment without the need for antibodies (Tan et al., 2023).</li>
<li><strong>Drug Target Identification for Coronavirus:</strong> 2-bromopalmitate (2-BP) can be used as an inhibitor and is used to suppressed SADS-CoV treatment (Luo et al., 2021).</li>
<li><strong>Cancer Therapy Enhancement:</strong> This compound has shown efficacy in sensitizing osteosarcoma cells to adriamycin-induced apoptosis through modulation of CHOP, indicating its therapeutic potential in enhancing cancer treatment (Xu et al., 2019).</li>
<li><strong>Membrane Protein Localization in Sertoli Cells: </strong>It has been involved in studies related to the localization of the androgen receptor to plasma membranes by binding to caveolin-1 in mouse Sertoli cells, contributing to the understanding of cellular signaling pathways. It is Used to inhibit palmitoylation of androgen receptor (AR) and used to evaluate the effect of the inhibitor on androgen receptor (AR) translocation (Deng et al., 2017).</li>
<li><strong>Palmitoylation Inhibition:</strong> 2-Bromohexadecanoic acid has been profiled as an irreversible inhibitor of palmitoylation, providing insights into the regulation of protein modifications and their implications in various diseases (Davda et al., 2013).</li>
</ul>

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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Oil-Filled Lipid Nanoparticles Containing 2?-(2-Bromohexadecanoyl)-Docetaxel for the Treatment of Breast Cancer
Lan F, et al.
Advanced Healthcare Materials, 2, 1451-1457 (2013)
Molecular Dynamics Simulation Studies of Self-Assembly of Racemic (R)/(S)-2-Bromohexadecanoic Acid on a Graphite Surface: Enantio-pure or Enantio-mixed Domains?.
Ilan B, et al.
The Journal of Physical Chemistry C, 111(49), 18243-18250 (2007)
Antibacterial and biofilm prevention metabolites from Acanthophora spicifera
Fitri B, et al.
open chemistry, 21, 20230163-20230163 (2023)
I Nagase et al.
FEBS letters, 461(3), 319-322 (1999-11-24)
Uncoupling protein 3 (UCP3), expressed abundantly in the skeletal muscle, is one of the carrier proteins dissipating the transmitochondrial electrochemical gradient as heat, and thereby has been implicated in the regulation of energy metabolism. We have investigated UCP3 mRNA expression
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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