15-Hexadecynoic acid

Base Information

• Chemical Name: 15-Hexadecynoic acid
• CAS No.: 99208-90-9
• Molecular Formula: C16H28O2
• Molecular Weight: 252.397
• Hs Code.: 2916190090
• DSSTox Substance ID: DTXSID70243987
• Nikkaji Number: J3.283.050A
• Wikidata: Q83128217
• Mol file: 99208-90-9.mol

Synonyms:15-hexadecynoic acid

Chemical Property of 15-Hexadecynoic acid

Chemical Property:

• Vapor Pressure: 1.5E-06mmHg at 25°C
• Melting Point: 59.1°C (estimate)
• Refractive Index: 1.4217 (estimate)
• Boiling Point: 371.8°C at 760 mmHg
• Flash Point: 180.7°C
• PSA: 37.30000
• Density: 0.931g/cm³
• LogP: 4.77550
• Storage Temp.: -20°C
• XLogP3: 6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 13
• Exact Mass: 252.208930132
• Heavy Atom Count: 18
• Complexity: 237

Purity/Quality:

97% ^*data from raw suppliers

Alkyne-palmiticacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCCCCCCCCCCCCC(=O)O
• Description: Alkynyl palmitic acid can be used to identify and characterize the post-translational S-palmitoylation of proteins with Click Chemistry.
• Uses: 15-hexadecynoic acid 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. The use of palmitic acid alkyne and related lipids in isolating palmitoylated proteins has been described. Palmitic acid (15-yne) has been used as a component of fatty acid probe stock solution for the optimization of Alk-C16 incorporation onto cellular proteins. It is also suitable for metabolic labeling.

Technology Process of 15-Hexadecynoic acid

There total 17 articles about 15-Hexadecynoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

9,10-dibromo-hexadecanoic acid (77503-27-6) → 15-hexadecyn-1-oic acid (99208-90-9)

Guidance literature:

With sodium amide; In toluene; at 20 - 120 ℃; for 9h; Cooling with ice;

Reference yield: 88.0%

jones' reagent + hexadec-7-yn-1-ol (822-21-9) + diamino propane (DAP) + hexadec-15-yn-1-ol (62914-53-8) + isopropyl alcohol (67-63-0,8013-70-5) → 15-hexadecyn-1-oic acid (99208-90-9)

Guidance literature:

With NaH; In ethyl acetate; acetone; mineral oil;

Reference yield: 86.0%

hexadec-15-yn-1-ol (62914-53-8) → 15-hexadecyn-1-oic acid (99208-90-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; for 9h;

DOI:10.1021/ja00068a017

upstream raw materials:

hexadec-15-yn-1-ol

n-2-hexadecyn-1-ol

2-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran

2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran

Downstream raw materials:

1,2-di-O-(15-hexadecyn-1-ol)-3-benzyl-sn-glycerol

2-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol

1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol

Hexadec-15-ynoic acid (S)-3-benzyloxy-2-hydroxy-propyl ester