18263-25-7 Usage
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
Check Digit Verification of cas no
The CAS Registry Mumber 18263-25-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,2,6 and 3 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 18263-25:
(7*1)+(6*8)+(5*2)+(4*6)+(3*3)+(2*2)+(1*5)=107
107 % 10 = 7
So 18263-25-7 is a valid CAS Registry Number.
InChI:InChI=1/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)/t15-/m0/s1
18263-25-7Relevant articles and documents
Tritium labelling of the GLP-1 analogue liraglutide
Larsen, Uffe S.,Hansen, Heidi B.,Dahl, Anne-Mette,Sorensen, Lone,Kristensen, Jesper B.
, p. 549 - 550 (2007)
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A Method for preparing alpha-olefins from Biomass-derived fat and oil
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Paragraph 0143-0146, (2020/09/22)
The present invention relates to a method for preparing alpha-olefins from biomass-derived fats and oils. According to the preparation method, all of the various saturated or unsaturated fatty acids in the biomass-derived fats and oils can be prepared into alpha-olefins, and a conventional problem that the saturated fatty acids do not participate in a reaction or a mixture is generated due to polyunsaturated fatty acids can be solved. Thus, the present invention can be advantageously used to prepare alpha-olefins from biomass.
Syntheses of 2-(2-Hydroxyethylamino) Fatty Acids
Xianxian, Du
, p. 123 - 124 (2007/10/02)
Eight 2-(2-hydroxyethylamino) fatty acids, 2-(2-hydroxyethylamino)decanoic, -undecanoic, -dodecanoic, -tetradecanoic, -hexadecanoic, -octadecanoic, -nonadecanoic, and docosanoic acid, were synthesized by reacting 2-bromo fatty acids with more than 3 mol of 2-aminoethanol.The surface tension and the critical micelle concentration were determined for these compounds.
