2-BROMOHEXADECANOIC ACID
- Product Name
- 2-BROMOHEXADECANOIC ACID
- CAS No.
- 18263-25-7
- Chemical Name
- 2-BROMOHEXADECANOIC ACID
- Synonyms
- 2-bromopalmitate;2-BROMOPALMITIC ACID;Hexadecanoic acid, 2-bromo-;ALPHA-BROMOPALMITATE;α-Bromopalmitic acid;A-BROMOPALMITIC ACID;Bromohexadecanoicacid;2-bromo-hexadecanoicaci;2-BROMOHEXADECANOIC ACID;2-Bromohexadecanoicacid97%
- CBNumber
- CB6143327
- Molecular Formula
- C16H31BrO2
- Formula Weight
- 335.32
- MOL File
- 18263-25-7.mol
2-BROMOHEXADECANOIC ACID Property
- Melting point:
- 52-54 °C
- Boiling point:
- 403.4±18.0 °C(Predicted)
- Density
- 1.1985 (rough estimate)
- refractive index
- 1.4650 (estimate)
- Flash point:
- 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 and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 238422
- Product name
- 2-Bromohexadecanoic acid
- Purity
- ~97%
- Packaging
- 10g
- Price
- $51.4
- Updated
- 2024/03/01
- Product number
- 21604
- Product name
- 2-Bromohexadecanoic acid
- Purity
- ≥99.0% (GC)
- Packaging
- 1g
- Price
- $102
- Updated
- 2024/03/01
- Product number
- 238422
- Product name
- 2-Bromohexadecanoic acid
- Purity
- ~97%
- Packaging
- 50g
- Price
- $197
- Updated
- 2024/03/01
- Product number
- 2121-9-00
- Product name
- 2-Bromohexadecanoic acid
- Packaging
- 50g
- Price
- $221
- Updated
- 2021/12/16
- Product number
- orb546166
- Product name
- 2-bromopalmitic acid
- Purity
- >98%
- Packaging
- 2g
- Price
- $244.8
- Updated
- 2021/12/16
2-BROMOHEXADECANOIC ACID Chemical Properties,Usage,Production
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
Raw materials
Preparation Products
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