| Identification | More | [Name]
2-BROMOHEXADECANOIC ACID | [CAS]
18263-25-7 | [Synonyms]
2-BROMOHEXADECANOIC ACID
2-BROMOPALMITIC ACID
A-BROMOPALMITIC ACID
2-bromo-hexadecanoicaci
2-bromopalmitate
2-BROMOHEXADECANOIC ACID (2-Bromopalmitic Acid)
ALPHA-BROMOPALMITATE
Bromohexadecanoicacid
2-Bromohexadecanoic acid, 98 %
α-Bromopalmitic acid | [EINECS(EC#)]
242-137-0 | [Molecular Formula]
C16H31BrO2 | [MDL Number]
MFCD00004215 | [Molecular Weight]
335.32 | [MOL File]
18263-25-7.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE CRYSTALLINE POWDER | [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 | [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. | [InChI]
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) | [InChIKey]
DPRAYRYQQAXQPE-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C(Br)CCCCCCCCCCCCCC | [CAS DataBase Reference]
18263-25-7(CAS DataBase Reference) | [EPA Substance Registry System]
Hexadecanoic acid, 2-bromo- (18263-25-7) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [TSCA ]
TSCA listed | [REACH Registrations]
Active | [HS Code ]
2915907098 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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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| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
|