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| 2-BROMOHEXADECANOIC ACID Basic information |
| 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) | | Fp | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 2915907098 |
| 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 |
| 2-BROMOHEXADECANOIC ACID Preparation Products And Raw materials |
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