2-BROMOHEXADECANOIC ACID

Synonym(s):2-Bromopalmitic acid

CAS NO.：18263-25-7
Empirical Formula: C16H31BrO2
Molecular Weight: 335.32
MDL number: MFCD00004215
EINECS: 242-137-0
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-19 18:29:52

What is 2-BROMOHEXADECANOIC ACID?

Description

2-Bromopalmitic acid (18263-25-7) inhibits?protein S-palmitoylation.1 Blocks palmitic acid-induced increase in cAMP levels in human primary melanocytes expressing the melanocortin-1 receptor which undergoes an essential palmitoylation as a prerequisite for receptor signaling.2

Chemical properties

WHITE CRYSTALLINE POWDER

The Uses of 2-BROMOHEXADECANOIC ACID

2-Bromopalmitic Acid is used in preparation of substituted purines and their analogs for inhibiting the expression of a pattern recognition receptor.

What are the applications of Application

2-Bromohexadecanoic acid is a PPARδ agonist

Definition

ChEBI: A bromo fatty acid that is hexadecanoic (palmitic) acid carrying a single bromo substituent at position 2.

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.

Purification Methods

Recrystallise the acid from pet ether (b 60-80o, charcoal) and finally from EtOH. The ethyl ester has b 177-178o/2mm, d28 1.0484, n D 1.4560. [IR: Sweet & Estes J Org Chem 21 1426 1956, Beilstein 2 IV 1184.]

References

1) Tsukamoto et al. (2013), Role of S-palmitoylation on IFITM5 for the interaction with FKBP11 in osteoblast cells; PLoS One, 8(9) e75831 2) Chen et al. (2017), Palmitoylation-dependent activation of MC1R prevents melanomagenesis; Nature, 549 399

Properties of 2-BROMOHEXADECANOIC ACID

Melting point:	52-54 °C
Boiling point:	403.4±18.0 °C(Predicted)
Density	1.1985 (rough estimate)
refractive index	1.4650 (estimate)
Flash point:	113 °C
storage temp.	RT
solubility	methanol: soluble1g/10 mL, clear, colorless
form	solid
pka	2.97±0.21(Predicted)
color	White
BRN	1726517
Stability:	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
CAS DataBase Reference	18263-25-7(CAS DataBase Reference)
EPA Substance Registry System	Hexadecanoic acid, 2-bromo- (18263-25-7)

Safety information for 2-BROMOHEXADECANOIC ACID

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.