18263-25-7 Usage
Uses
Used in Pharmaceutical Industry:
2-Bromohexadecanoic acid is used as a ligand for the PPARδ receptor to modulate gene expression and lipid metabolism. It helps in the development of drugs targeting the PPARδ receptor for various therapeutic applications.
Used in Biochemical Research:
2-Bromohexadecanoic acid is used as a research tool in studies of fatty acid oxidation, palmitoylation, and glucose uptake. It aids in understanding the role of fatty acids in cellular processes and their potential implications in disease mechanisms.
Used in Preparation of Substituted Purines:
2-Bromohexadecanoic acid is used in the preparation of substituted purines and their analogs for inhibiting the expression of a pattern recognition receptor. This application is relevant in the development of drugs targeting specific receptors for therapeutic purposes.
Used in Inhibition of Protein S-Palmitoylation:
2-Bromohexadecanoic acid is used as an inhibitor of protein S-palmitoylation, which is a post-translational modification involved in various cellular processes. It blocks the palmitic acid-induced increase in cAMP levels in human primary melanocytes expressing the melanocortin-1 receptor, which undergoes essential palmitoylation for receptor signaling.
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 academic research and scientific papers
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.
Mesoionic 5-alkyl-1,3-dithiolium-4-thiolates: Synthesis and brine shrimp toxicity
De Almeida, Paulo Afonso,Da Silva, Tania Maria Sarmento,Echevarria, Aurea
, p. 593 - 600 (2007/10/03)
A series of twelve 1,3-dithiolium-4-thiolate mesoionic compounds were synthesized and characterized. The synthetical approach starting from α-bromoalkanoic acids to obtain the corresponding 2-N-morpholino-dithiocarbamoyl-carboxylic acids that by on-pot reaction with carbon disulfide and acetic anhydride in triethylamine formed not isolate intermediates, 1,3-dithiolium-4-olates. After, the 2-N-morpholino-5-alkyl-1,3-dithiolium-4-thiolates were obtained by retro 1,3-dipolar addition reactions. The alkyl moiety linked to C-5 of heterocyclic ring permitted the increase of the hydrophobic character and this effect was evaluated on Artemia salina lethality. The results indicated a bell-shaped relationship between the number of carbon of side chain in mesoionic derivatives and LD50 in brine shrimp toxicity assays.
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.
