2-BROMOHEXADECANOIC ACID Chemical Properties

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

pka

2.97±0.21(Predicted)

form 

solid

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2915907098

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-BROMOHEXADECANOIC ACID Usage And Synthesis

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

Uses

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

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

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