15-Hexadecynoic acid

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Category	Click Reagents
Catalog NO.	BPG-3018
Product Name	15-Hexadecynoic acid
CAS	99208-90-9
Molecular Formula	C16H28O2
Molecular Weight	252.39

Scheme Design
Custom Synthesis
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Product Information
Application
References
Documents
Reviews

Product Information

Description	Palmitic acid alkyne is a form of palmitic acid with an ω-terminal alkyne. The terminal alkyne group can be used in linking reactions, known as click chemistry; this chemistry is characterized by high dependability and specificity of the azide-alkyne bioconjugation reactions. Alkynyl palmitic acid can be used for isolating palmitoylated proteins.
Synonyms	Palmitic acid (15-yne); Alkynyl Palmitic Acid; 15-Hexadecyn-1-oic acid
IUPAC Name	hexadec-15-ynoic acid
Canonical SMILES	C#CCCCCCCCCCCCCCC(=O)O
InChI	InChI=1S/C16H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h1H,3-15H2,(H,17,18)
InChIKey	PUZGUNYANHPRKM-UHFFFAOYSA-N
Purity	>99%
Solubility	In DMSO: 100 mg/mL (396.21 mM; Need ultrasonic)
Appearance	Powder
Shelf Life	1 Year
Storage	Store at -20°C
Exact Mass	252.209
Hygroscopic	No
Light Sensitive	No
Percent Composition	C 76.14%, H 11.18%, O 12.68%

References

1. Ticho AL, Malhotra P, Manzella CR, Dudeja PK, Saksena S, Gill RK, Alrefai WA. S-Acylation modulates the function of the apical sodium-dependent bile acid transporter in human cells. J Biol Chem. 2020 Feb 18:jbc.RA119.011032. doi: 10.1074/jbc.RA119.011032. Epub ahead of print. PMID: 32071081. PubMed ID: 32071081.
2. Tallman KA, Armstrong MD, Milne SB, Marnett LJ, Brown HA, Porter NA. Cobalt carbonyl complexes as probes for alkyne-tagged lipids. J Lipid Res. 2013 Mar;54(3):859-68. doi: 10.1194/jlr.D033332. Epub 2013 Jan 10. PMID: 23307946; PMCID: PMC3617960. PubMed ID: 23307946.
3. Milne SB, Tallman KA, Serwa R, Rouzer CA, Armstrong MD, Marnett LJ, Lukehart CM, Porter NA, Brown HA. Capture and release of alkyne-derivatized glycerophospholipids using cobalt chemistry. Nat Chem Biol. 2010 Mar;6(3):205-207. doi: 10.1038/nchembio.311. Epub 2010 Jan 24. PMID: 20098428; PMCID: PMC2822082. PubMed ID: 20098428.
4. Jiang H, Khan S, Wang Y, Charron G, He B, Sebastian C, Du J, Kim R, Ge E, Mostoslavsky R, Hang HC, Hao Q, Lin H. SIRT6 regulates TNF-α secretion through hydrolysis of long-chain fatty acyl lysine. Nature. 2013 Apr 4;496(7443):110-3. doi: 10.1038/nature12038. PMID: 23552949; PMCID: PMC3635073. PubMed ID: 23552949.
5. Thiele C, Papan C, Hoelper D, Kusserow K, Gaebler A, Schoene M, Piotrowitz K, Lohmann D, Spandl J, Stevanovic A, Shevchenko A, Kuerschner L. Tracing fatty acid metabolism by click chemistry. ACS Chem Biol. 2012 Dec 21;7(12):2004-11. doi: 10.1021/cb300414v. Epub 2012 Oct 2. PMID: 22999348. PubMed ID: 22999348.
6. Gao X, Arenas-Ramirez N, Scales SJ, Hannoush RN. Membrane targeting of palmitoylated Wnt and Hedgehog revealed by chemical probes. FEBS Lett. 2011 Aug 4;585(15):2501-6. doi: 10.1016/j.febslet.2011.06.033. Epub 2011 Jul 2. PMID: 21740904. PubMed ID: 21740904.
7. Yap MC, Kostiuk MA, Martin DD, Perinpanayagam MA, Hak PG, Siddam A, Majjigapu JR, Rajaiah G, Keller BO, Prescher JA, Wu P, Bertozzi CR, Falck JR, Berthiaume LG. Rapid and selective detection of fatty acylated proteins using omega-alkynyl-fatty acids and click chemistry. J Lipid Res. 2010 Jun;51(6):1566-80. doi: 10.1194/jlr.D002790. Epub 2009 Dec 21. PMID: 20028662; PMCID: PMC3035521. PubMed ID: 20028662.
8. Martin BR, Cravatt BF. Large-scale profiling of protein palmitoylation in mammalian cells. Nat Methods. 2009 Feb;6(2):135-8. doi: 10.1038/nmeth.1293. Epub 2009 Jan 11. PMID: 19137006; PMCID: PMC2775068. PubMed ID: 19137006.

Reviews

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