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18263-25-7

18263-25-7 Structure

18263-25-7 Structure
IdentificationMore
[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 PropertiesBack 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.
[CAS DataBase Reference]

18263-25-7(CAS DataBase Reference)
[EPA Substance Registry System]

Hexadecanoic acid, 2-bromo- (18263-25-7)
Safety DataBack 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
Hazard InformationBack 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
Spectrum DetailBack Directory
[Spectrum Detail]

2-BROMOHEXADECANOIC ACID(18263-25-7)MS
2-BROMOHEXADECANOIC ACID(18263-25-7)1HNMR
2-BROMOHEXADECANOIC ACID(18263-25-7)13CNMR
2-BROMOHEXADECANOIC ACID(18263-25-7)IR1
2-BROMOHEXADECANOIC ACID(18263-25-7)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

18263-25-7(sigmaaldrich)
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