99208-90-9

Basic information

• Product Name: 15-hexadecynoic acid
• Synonyms: 15-hexadecynoic acid;Palmitic Acid Alkyne;hexadec-15-ynoic acid;Palmitic acid (15-yne);Alkynyl Palmitic Acid
• CAS NO: 99208-90-9
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.39
• Mol File: 99208-90-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 59.1°C (estimate)
• Boiling Point: 409.64°C (rough estimate)
• Flash Point: 180.7°C
• Appearance: /
• Density: 0.9310 (rough estimate)
• Vapor Pressure: 1.5E-06mmHg at 25°C
• Refractive Index: 1.4217 (estimate)
• Storage Temp.: -20°C
• CAS DataBase Reference: 15-hexadecynoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 15-hexadecynoic acid(99208-90-9)
• EPA Substance Registry System: 15-hexadecynoic acid(99208-90-9)

Safety Data

• Hazardous Substances Data: 99208-90-9(Hazardous Substances Data)

Usage

Description

15-Hexadecynoic acid, also known as palmitic acid (15-yne), is a form of palmitic acid with an ω-terminal alkyne group. This terminal alkyne group allows for versatile linking reactions through click chemistry, which is characterized by high dependability and specificity in azide-alkyne bioconjugation reactions. The use of 15-hexadecynoic acid and related lipids has been instrumental in the isolation and study of palmitoylated proteins.

Uses

Used in Biochemistry Research:
15-Hexadecynoic acid is used as a biochemical tool for identifying and characterizing the post-translational S-palmitoylation of proteins. This process involves the covalent attachment of palmitic acid to specific cysteine residues on target proteins, which can modulate their function, localization, and interactions within the cell.
Used in Drug Delivery Systems:
In the field of drug delivery, 15-hexadecynoic acid can be utilized as a component in the development of novel drug carriers. The terminal alkyne group facilitates the attachment of therapeutic agents or imaging probes to the carrier molecules through click chemistry, potentially improving the targeting and efficacy of drug delivery systems.
Used in Metabolic Labeling:
15-Hexadecynoic acid, specifically palmitic acid (15-yne), is used as a component of fatty acid probe stock solutions for the optimization of Alk-C16 incorporation onto cellular proteins. This application is particularly useful in metabolic labeling studies, where researchers aim to track the incorporation and turnover of lipids within cells.
Used in Protein Isolation:
The terminal alkyne group of 15-hexadecynoic acid allows for its use in the isolation of palmitoylated proteins. This is achieved through click chemistry-based techniques, where the alkyne group can be selectively reacted with azide-containing probes or beads, enabling the enrichment and analysis of proteins modified by palmitic acid.

Biochem/physiol Actions

Alkynyl palmitic acid (aPA) is a modified palmitic acid with an ω-terminal alkyne. The terminal alkyne group can be used in a highly specific linking reaction with azide-containing reagents, known as ‘click chemistry′. The click chemistry reactions are rapid, convenient, versatile and regiospecific. They are easy to purify. aPA can be used for isolating palmitoylated proteins.

InChI:InChI=1/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)

Upstream product

• 62914-53-8 hexadec-15-yn-1-ol 
• 2833-99-0 n-2-hexadecyn-1-ol 
• 119290-95-8 2-(hexadec-2-yn-1-yloxy)tetrahydro-2H-pyran 
• 52056-69-6 2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 765-13-9 pentadec-1-yne 
• 145205-01-2 12-Hexadecyn-1-ol THP ether 
• 144002-31-3 12-hexadecyn-1-ol 
• 822-21-9 hexadec-7-yn-1-ol 
• 67-63-0 isopropyl alcohol 
• 4617-33-8 15-hydroxylpentadecanoic acid 
• 76529-42-5 methyl 15-hydroxypentadecanoate 
• 1931-69-7 15-oxo-pentadecanoic acid methyl ester 
• 77503-27-6 9,10-dibromo-hexadecanoic acid 

Downstream Products

• 149221-80-7 1,2-di-O-(15-hexadecyn-1-ol)-3-benzyl-sn-glycerol 
• 139100-94-0 2-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol 
• 139100-84-8 1-palmitoyl-2-(15-hexadecyn-1-oyl)-3-(4-methoxybenzyl)-sn-glycerol 
• 183144-92-5 Hexadec-15-ynoic acid (S)-3-benzyloxy-2-hydroxy-propyl ester 
• 183145-01-9 Hexadec-15-ynoic acid (S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl ester 
• 183145-12-2 Dotriaconta-15,17-diynedioic acid bis-[(S)-3-benzyloxy-2-(12-methoxy-dodecanoyloxy)-propyl] ester 
• 149221-83-0 1,2-O-(15,17-dotriacontadiyne-1,32-dioyl)-3-benzyl-sn-glycerol 
• 139100-87-1 2,2'-(15,17-dotriacontadiyne-1,32-dioyl)bis(1-palmitoyl-3-(4-methoxybenzyl)-sn-glycerol) 
• 505-54-4 thapsic acid 

Relevant articles and documents

Preparation method of long-chain diacid

The invention provides a preparation method of long-chain diacid, which comprises the following steps of: (S1) carrying out an addition reaction on olefine acid or an ester derivative thereof serving as a raw material and liquid bromine to obtain dibromo carboxylic acid or an ester derivative thereof; (S2) carrying out an elimination reaction on the dibromo carboxylic acid or ester derivative thereof under the action of sodium amide to obtain alkynyl-terminated carboxylic acid or an ester derivative thereof; (S3) carrying out an addition reaction on the alkynyl-terminated carboxylic acid or the ester derivative thereof and diborane to obtain borane or boric acid containing carboxyl or ester group; and (S4) oxidizing the borane or boric acid to obtain long-chain diacid. According to the invention, olefine acid is used as a raw material, is easily available in source and low in price, so that the production cost of the product is very low; and meanwhile, the raw materials used in the synthesis process do not contain precious metals or other expensive reagents, so that the synthesis process is suitable for industrial amplification production, and the defect that the method in the prior art is not environment-friendly, not suitable for industrial production and high in preparation cost is overcome.

Effect of carbon chain length in acyl coenzyme A on the efficiency of enzymatic transformation of okadaic acid to 7-O-acyl okadaic acid

Okadaic acid (OA), a product of dinoflagellate Prorocentrum spp., is transformed into 7-O-acyl OA in various bivalve species. The structural transformation proceeds enzymatically in vitro in the presence of the microsomal fraction from the digestive gland of bivalves. We have been using LC-MS/MS to identify OA-transforming enzymes by detecting 7-O-acyl OA, also known as dinophysistoxin 3 (DTX3). However, an alternative assay for DTX3 is required because the OA-transforming enzyme is a membrane protein, and surfactants for solubilizing membrane proteins decrease the sensitivity of LC-MS/MS. The present study examined saturated fatty acyl CoAs with a carbon chain length of 10 (decanoyl), 12 (dodecanoyl), 14 (tetradecanoyl), 16 (hexadecanoyl) and 18 (octadecanoyl) as the substrate for the in vitro acylation reaction. Saturated fatty acyl CoAs with a carbon chain length of 14, 16 and 18 exhibited higher yields than those with a carbon chain length of 10 or 12. Acyl CoAs with carbon chain lengths from 14 to 18 and containing either a diene unit, an alkyne unit, or an azide unit in the carbon chain were synthesized and shown to provide the corresponding DTX3 with a yield comparable to that of hexadecanoyl CoA. The three functional units can be conjugated with fluorescent reagents and are applicable to the development of a novel assay for DTX3.

Robust fluorescent detection of protein fatty-acylation with chemical reporters

Fatty-acylation of proteins in eukaryotes is associated with many fundamental cellular processes but has been challenging to study due to limited tools for rapid and robust detection of protein fatty-acylation in cells. The development of azido-fatty acid