2-Bromohexadecanoic acid (2-Bromopalmitic acid) is a 2-bromopalmitic acid that can be converted to 2-bromopalmitate (2-BP). 2-BP is a palmitoylation inhibitor that targets the DHHC (Asp-His-His-Cys) protein palmitoyltransferase. 2-BP inhibits the palmitoylation of GSDME-C and inhibits pyroptosis mediated by the BAK/BAX-Caspase 3-GSDME pathway.

Physicochemical Properties

Molecular Formula	C16H31BRO2
Molecular Weight	335.32
Exact Mass	334.15
Elemental Analysis	C, 57.31; H, 9.32; Br, 23.83; O, 9.54
CAS #	18263-25-7
PubChem CID	82145
Appearance	White to yellow solid
Density	1.1±0.1 g/cm3
Boiling Point	403.4±18.0 °C at 760 mmHg
Melting Point	52-54 °C
Flash Point	197.8±21.2 °C
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.480
LogP	7.76
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	14
Heavy Atom Count	19
Complexity	207
Defined Atom Stereocenter Count	0
SMILES	CCCCCCCCCCCCCCC(C(=O)O)Br
InChi Key	DPRAYRYQQAXQPE-UHFFFAOYSA-N
InChi Code	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)
Chemical Name	2-bromohexadecanoic acid
Synonyms	2-bromopalmitate; 2-BP; 2-Bromopalmitate; 2BP; 2-Bromopalmitic acid; 2 BP; 2 Bromopalmitate; 2Bromopalmitate; 2Bromopalmitic acid; 2 Bromopalmitic acid;
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	After GSDME-N is cleaved, palmitoylation encourages the release of GSDME-C, whereas 2-BP prevents palmitoylation, prevents GSDME-C from being modified, and increases the interaction between GSDME-C and GSDME-N. 2-BP prevents apoptosis brought on by TNFa+CHX, but not complete cell death [1].
Cell Assay	For navitoclax or TNFα+CHX treatments, cells were pre-seeded overnight until cell density reached ~60%. The culture medium was switched to fresh medium containing relevant drugs and incubated for a period of time as indicated. To inhibit caspase activity or palmitoylation, cells were pre-incubated for 1 h with Q-VD-OPh or 2-BP, respectively. Unless otherwise specified, the concentrations of the drugs used are: 2 μM for navitoclax, 20 ng/mL for TNFα, 10 μg/mL for CHX, 50 μM for Q-VD-OPh, 50 μM for 2-BP, and 50 μM for actinomycin D [1].
References	[1]. Chemotherapy-induced pyroptosis is mediated by BAK/BAX-caspase-3-GSDME pathway and inhibited by 2-bromopalmitate. Cell Death Dis. 2020 Apr 24;11(4):281.
Additional Infomation	2-bromohexadecanoic acid is a bromo fatty acid that is hexadecanoic (palmitic) acid carrying a single bromo substituent at position 2. It has a role as a fatty acid oxidation inhibitor. It is a bromo fatty acid, a straight-chain fatty acid, a long-chain fatty acid and a 2-bromocarboxylic acid. It is functionally related to a hexadecanoic acid.

Solubility Data

Solubility (In Vitro)

DMSO : 100 mg/mL (298.22 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (7.46 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.46 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.9822 mL	14.9111 mL	29.8223 mL
	5 mM	0.5964 mL	2.9822 mL	5.9645 mL
	10 mM	0.2982 mL	1.4911 mL	2.9822 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.