2-Brompalmitinsure

Bezeichnung:2-Brompalmitinsure

CAS-Nr18263-25-7

Englisch Name:2-Bromohexadecanoic acid

CBNumberCB6143327

SummenformelC16H31BrO2

Molgewicht335.32

MOL-Datei18263-25-7.mol

Synonyma

2-Brompalmitinsure

2-Brompalmitinsure physikalisch-chemischer Eigenschaften

Schmelzpunkt	52-54 °C
Siedepunkt	403.4±18.0 °C(Predicted)
Dichte	1.1985 (rough estimate)
Brechungsindex	1.4650 (estimate)
Flammpunkt	113 °C
storage temp.	RT
Löslichkeit	methanol: soluble1g/10 mL, clear, colorless
pka	2.97±0.21(Predicted)
Aggregatzustand	solid
Farbe	White
BRN	1726517
Stabilität	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 Datenbank	18263-25-7(CAS DataBase Reference)
EPA chemische Informationen	Hexadecanoic acid, 2-bromo- (18263-25-7)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-36
WGK Germany	3
TSCA	TSCA listed
HS Code	2915907098
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

2-Bromohexadecanoic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
2-Bromopalmitic acid (18263-25-7) inhibitsprotein 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
Chemische Eigenschaften
WHITE CRYSTALLINE POWDER
Verwenden
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.
Allgemeine Beschreibung
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.
läuterung methode
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.]
Einzelnachweise
[1] TAKASHI TSUKAMOTO. Role of S-palmitoylation on IFITM5 for the interaction with FKBP11 in osteoblast cells.[J]. PLoS ONE, 2013: e75831. DOI:10.1371/journal.pone.0075831
[2] SHUYANG CHEN. Palmitoylation-dependent activation of MC1R prevents melanomagenesis[J]. Nature, 2017, 549 7672: 399-403. DOI:10.1038/nature23887

2-Bromohexadecanoic acid Upstream-Materialien And Downstream Produkte

2-Brompalmitinsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

18263-25-7, 2-Bromohexadecanoic acid Verwandte Suche:

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