623-65-4

Basic information

• Product Name: Palmitic anhydride
• Synonyms: hexadecanoicacid,anhydride;PALMITIC ANHYDRIDE;HEXADECANOIC ANHYDRIDE;PALMITIC ANHYDRIDE (C16:0) GRADE II;PALMITIC ANHYDRIDE (C16:0) GRADE I;Palmitic anhydride 99+%;Bishexadecanoic anhydride;Bispalmitic anhydride
• CAS NO: 623-65-4
• Molecular Formula: C₃₂H₆₂O₃
• Molecular Weight: 494.83
• EINECS: 210-805-0
• Product Categories: Anhydrides;Biochemicals and Reagents;Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Lipids;Organic Building Blocks;Saturated Fatty Acids and Derivatives
• Mol File: 623-65-4.mol
• Article Data: 26

Chemical Properties

• Melting Point: 61-64 °C(lit.)
• Boiling Point: 547.77°C (rough estimate)
• Flash Point: 220.6 °C
• Appearance: white powder
• Density: 0.8388
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Refractive Index: 1.4364 (estimate)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Toluene
• BRN: 1807507
• CAS DataBase Reference: Palmitic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: Palmitic anhydride(623-65-4)
• EPA Substance Registry System: Palmitic anhydride(623-65-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 623-65-4(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Palmitic anhydride was used in the synthesis of water-soluble N-palmitoyl chitosan (PLCS) by coupling with swollen chitosan in dimethyl sulfoxide (DMSO). It was also used in the synthesis of N-acylphosphatidylserine.

General Description

Palmitic anhydride reacted with 20-methyl spirolide G to form a derivative with a retention time and spectrum identical with the metabolite, 17-O-palmitoyl-20-methyl spirolide G.

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

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

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 
• 55726-45-9 N⁴-Palmitoyl-1-β-D-arabinofuranosylcytosin 
• 156832-59-6 Hexadecanoic acid (R)-1-[benzyloxy-(2-bromo-ethoxy)-phosphoryloxymethyl]-2-trityloxy-ethyl ester 
• 156832-50-7 (2R)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol 
• 156832-41-6 (2S)-1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-2-O-palmitoyl-3-O-(tert-butyldimethylsilyl)glycerol 
• 9004-94-8 2-(2-(2-hydroxyethoxy)ethoxy)ethyl palmitate 
• 73130-89-9 riboflavin-5'-monopalmitate 
• 66591-30-8 S-(benzyl)hexadecanethioate 
• 87944-76-1 2-palmitoylcyclohexane-1,3-dione 
• 63-89-8 L-α-Dipalmitoylphosphatidylcholine 
• 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 
• 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 

Relevant articles and documents

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.

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.

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.