623-65-4

Usage

Uses

1. Used in Pharmaceutical Industry:
Palmitic anhydride is used as a synthetic agent for the production of water-soluble N-palmitoyl chitosan (PLCS). This is achieved by coupling with swollen chitosan in dimethyl sulfoxide (DMSO), which enhances the solubility and bioavailability of chitosan for various pharmaceutical applications.
2. Used in Chemical Synthesis:
Palmitic anhydride is used as a reactant in the synthesis of N-acylphosphatidylserine, a compound with potential applications in the study and treatment of certain diseases.
3. Used in Analytical Chemistry:
Palmitic anhydride is used to form derivatives of specific compounds, such as 20-methyl spirolide G, to facilitate their identification and analysis. The reaction results in a derivative with a retention time and spectrum identical to the metabolite, 17-O-palmitoyl-20-methyl spirolide G, which can be useful in the detection and quantification of this metabolite in various samples.

Purification Methods

It is moisture sensitive and hydrolyses in water. Purify it by refluxing with acetic anhydride for 1hour, evaporating and freeing the residue of acetic acid and anhydride by drying the residue at high vacuum and recrystallising from pet ether at low temperature. [Beilstein 2 IV 1181.]

InChI:InChI=1/C32H62O3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31(33)35-32(34)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h3-30H2,1-2H3

Upstream product

• 408-35-5 sodium palmitate 
• 108-24-7 acetic anhydride 
• 57-10-3 1-hexadecylcarboxylic acid 
• 112-67-4 n-hexadecanoyl chloride 
• 3508-01-8 silver palmitate 
• 108-05-4 vinyl acetate 

Downstream Products

• 6533-53-5 4.4'-dipalmitoyloxy-α.α'-diethyl-trans-stilbene 
• 1763-10-6 S-palmitoyl-coenzyme A 
• 19698-29-4 1,2-Dipalmitoylphosphatidic acid 
• 65237-39-0 3-O-<1-O-Palmitoylglycero-3-O-(O-benzyl)phosphoryl>-N-methyl-N-benzylpropanolamin 
• 65237-38-9 3-O-<1,2-Di-O-palmitoylglycero-3-O-(O-benzyl)phosphoryl>-N-methyl-N-benzylpropanolamin 
• 991-20-8 testosterone palmitate 
• 122470-18-2 3-O-hexadecyl-2-O-palmitoyl-sn-glycerol 1-p-toluenesulfonate 
• 122470-17-1 1-O-hexadecyl-2-O-palmitoyl-sn-glycerol 3-p-toluenesulfonate 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 123191-37-7 (2,3-Bis-hexadecanoyloxy-propyl)-[2-(3-ethoxycarbonyl-4-iodo-phenoxy)-ethyl]-dimethyl-ammonium; bromide 
• 88587-94-4 L-1-hexadecyl-2-palmitoyl-phosphatidylcholine 
• 137896-84-5 (2S,3R,4E) 2-azido-3-(benzoyloxy)-2-(hexadecanoylamino)-1-O-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene 
• 137896-94-7 (2S,3R,4E)-3-(benzoyloxy)-2-(hexadecanoylamino)-1-<(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>-4-octadecene 
• 141250-03-5 (2S,3R,4E)-3-(benzoyloxy)-2-(hexadecanoylamino)-1-<2,3,6-tri-O-acetyl-4,7-anhydro-4-C-(hydroxymethyl)-β-D-glucopyranosyloxy>-4-octadecene 

Relevant academic research and scientific papers

A Lipophilic Pt(IV) Oxaliplatin Derivative Enhances Antitumor Activity

Side effects and acquired resistance by cancer cells limit the use of platinum anticancer drugs. Modification of oxaliplatin (OXA) into a lipophilic Pt(IV) complex [Pt(DACH)(OAc)(OPal)(ox)] (1), containing both lipophilic and hydrophilic axial ligands, was applied to improve performance and facilitate incorporation into polymeric nanoparticles. Complex 1 exhibited unique potency against a panel of cancer cells, including cisplatin-resistant tumor cells. [Pt(DACH)(OAc)(OPal)(ox)] incorporated nanoparticles (2) presented a mean diameter of 146 nm with encapsulation yields above 95% as determined by HPLC. Complexes 1 and 2 showed enhanced in vitro cellular Pt accumulation, DNA platination, and antiproliferative effect compared to OXA. Results of an orthotopic intraperitoneal model of metastatic ovarian cancer (SKOV-3) and a xenograft subcutaneous model of colon (HCT-116) tumor in SCID-bg mice showed that the activity of 1 and 2 significantly decreased tumor growth rates compared to control and OXA treatment groups. Consequently, these findings warrant further development toward clinical translation.

Chemical synthesis of palmitoylated histone H4

Palmitoylation is one of the post-translational modifications of proteins. Recently, palmitoyl modification was found in histone H4, one of the components of the nucleosome core. To analyze this unusual modification in the nuclear protein, we chemically synthesized Ser47-palmitoylated histone H4. The entire sequence of H4 was divided into three segments and each was prepared by Fmoc-solid-phase peptide synthesis (SPPS). The palmitoyl group was introduced as a preformed palmitoyl Ser during SPPS or introduced at the end of SPPS by selective deprotection of the hydroxy group of Ser47, followed by palmitoylation. After three segments were condensed in one-pot by the thioester method, the desired Ser47-palmitoylated H4 was obtained.

Potential Vegetable-Based Diesel Fuels from Perkin Condensation of Furfuraldehyde and Fatty Acid Anhydrides

Domestically produced biofuels may help to reduce dependence on imported oil for powering transportation and infrastructure in the future. In this report, we reacted medium-chain and long-chain fatty anhydrides (capric, caprylic, lauric, and palmitic) with furfuraldehyde by the Perkin condensation to produce 2-n-alkenylfurans. In the second step, the 2-n-alkenylfurans were hydrogenated to form 2-n-alkyltetrahydrofurans. Basic fuel property testing (melting point, density, kinematic viscosity, derived cetane number, and calorific value) of the 2-n-alkyltetrahydrofurans indicates they are potentially useful as fuels for diesel engines. The mixture composed of 2-octyl- and 2-decyltetrahydrofuran had the best combination of fuel properties including a low melting point (?39 °C), high cetane number (63.1), high flash point (98.2 °C), and low viscosity (2.26 mm2 s?1, 40 °C), which compares favorably with specifications for diesel #2 and biodiesel.

METHOD FOR SEPARATING HIGH-BOILING CARBOXYLIC ACID VINYL ESTER/CARBOXYLIC ACID MIXTURES

The invention relates to a method for separating a mixture containing at least one carboxylic acid vinyl ester of general formula R′—C(O)O—CH═CH2 and at least one carboxylic acid of general formula R′—COOH, wherein R′ in either case can be an aliphatic group having 12 to 22 C atoms or a cycloaliphatic group having 12 to 22 C atoms, or an aromatic group having 12 to 22 C atoms, and R′ can be identical or different, characterized in that the carboxylic acid is converted to its anhydride R′—C(O)—O—C(O)—R′ and the carboxylic acid vinyl ester is subsequently separated.

A new synthesis route for the preparation of the avocadofuran (2-hexadecylfuran)

A new synthetic route for the preparation of the insecticidal compound 2-hexadecylfuran is described in this study. The procedure starts from readily available furfuraldehyde and palmitic anhydride via two steps employing the Perkin reaction and resulting in a 25% overall yield. The method can be deemed as a practical and environmentally friendly route to prepare a potentially important class of insecticide.

Use of glycerol carbonate in an efficient, one-pot and solvent free synthesis of 1,3-sn-diglycerides

An efficient solvent-free synthesis of a variety of highly pure 1,3-sn-diglycerides (1,3-sn-diacylglycerols) in a two-step one pot process is described. Heating glycerol carbonate (4-hydroxymethyl-1,3-dioxolan-2-one) with fatty acid anhydrides 2a-d affords 1:1 mixtures of glycerol carbonate fatty esters 3a-3d and the corresponding fatty acids. Further heating the reaction mixtures in the presence of catalytic amounts of 1,4-diazabicyclo[2.2.2]octane (DABCO) at 195-200 °C yields highly pure 1,3-sn-diglycerides 4a-4d.

First total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol-a glycoglycerolipid of a marine alga with a high inhibitor activity against human Myt1-kinase

The first total synthesis of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol, a glycoglycerolipid isolated from a marine alga extract, is described. Starting from α-methylglucopyranoside the multistep strategy allows the stereoselective synthesis of the final compound using various protective group procedures as well as derivatization of partial molecule domains. The latter offers the development of lead structures for inhibitors of human Myt1-kinase.

Facile synthesis of carboxylic anhydrides using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)-one

A novel and facile synthesis of carboxylic anhydrides from carboxylic acid using 4,5-dichloro-2-[(4-nitrophenyl)sulfonyl]pyridazin-3(2H)-one (2) is presented. Treatment of aliphatic or aromatic carboxylic acids with 2 in the presence of base in organic solvents gave the corresponding anhydrides in good or excellent yields.

A convenient method for synthesis of symmetrical acid anhydrides from carboxylic acids with trichloroacetonitrile and triphenylphosphine

Various carboxylic acids are converted into the corresponding carboxylic acid anhydrides treated with trichloroacetonitrile and triphenylphosphine in the presence of triethylamine at room temperature.

Synthesis and characterization of long chain alkyl acyl carnitine esters. Potentially biodegradable cationic lipids for use in gene delivery

A series of alkyl acyl carnitine esters (alkyl 3-acyloxy-4- trimethylammonium butyrate chloride) were synthesized as potential biocompatible cationic lipids for use in gene transfer. The physicochemical properties of the lipids, liposomes prepared from them, and their complexes with DNA were characterized by differential scanning calorimetry (DSC), particle size, potential, and surface monolayer measurements. The transition temperatures and behavior at an air-water interface for this series are similar to phosphatidylcholines with the same hydrocarbon chain length. The physical properties of the L derivatives were not significantly different from the DL derivatives. At 70 °C, the acyl chains were readily hydrolyzed at pH 7. The influence of the aliphatic chain length (n = 12-18) on transfection efficiency in vitro was determined using cationic liposomes prepared from these lipids or their mixtures with the helper lipids, dioleoylphosphatidylethanolamine (DOPE), dioleoylphosphatidylcholine, monooleoylglycerol, and cholesterol (Chol). The mixture of myristyl 3- myristoyloxy-4-trimethylammonium butyrate chloride (MMCE, 4d) with DOPE at a 1:1 molar ratio mediated the highest transfection efficiency in cell culture. The mixture of oleyl 3-oleoyloxy-4-trimethylammonium butyrate chloride (OOCE, 4f) with Chol at a 1:1 molar ratio gave the highest transfection efficiency after intravenous administration in mice. In vivo gene expression using 4f was comparable to values obtained with the best cationic lipids reported to date.