23470-00-0

Basic information

• Product Name: 2-MONOPALMITIN
• Synonyms: 2-monopalmitoylglycerol (C16:0);Glyceryl 2-monopalmitate;2-MONOOLEIN;2-Monohexadecanoylglycerol;2-Monopalmitoylglycerol;2-O-Hexadecanoylglycerol;2-O-Palmitoylglycerol;2-O-Palmitoyl-L-glycerol
• CAS NO: 23470-00-0
• Molecular Formula: C₁₉H₃₈O₄
• Molecular Weight: 330.5
• Product Categories: Cannabinoid receptor;Fatty Acid Derivatives & Lipids;Glycerols
• Mol File: 23470-00-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 68-70°C
• Boiling Point: 387.92°C (rough estimate)
• Flash Point: 150.8°C
• Appearance: /
• Density: 0.9708 (rough estimate)
• Refractive Index: 1.4434 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 13.54±0.10(Predicted)
• BRN: 1796692
• CAS DataBase Reference: 2-MONOPALMITIN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-MONOPALMITIN(23470-00-0)
• EPA Substance Registry System: 2-MONOPALMITIN(23470-00-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 23470-00-0(Hazardous Substances Data)

Usage

Description

2-Arachidonoyl glycerol (2-AG; ) is an endogenous agonist of the CB1 and CB2 cannabinoid receptors. 2-Palmitoyl glycerol is a fatty acid ester that does not bind directly to cannabinoid receptors, nor inhibit adenylyl cyclase, but rather potentiates the activity of 2-AG (and other endocannabinoids) to bind to CB1 and CB2 and inhibit adenylyl cyclase. This “entourage” effect has been attributed to blockade of the breakdown and reuptake pathways that normally function to reduce endocannabinoid levels rapidly upon release. 2-Palmitoyl glycerol and related endogenous fatty acid derivatives have been shown to interact with endocannabinoids in the modulation of pain sensitivity.

Chemical Properties

White Solid

Uses

A biomarker of metabolic responses to hepatotoxicants and carcinogens.

Definition

ChEBI: A 2-monoglyceride where the acyl group is hexadecanoyl (palmitoyl).

Biological Activity

Endogenous fatty acid glycerol ester that enhances activity of 2-arachidonylglycerol ((5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic acid,2-hydroxy-1-(hydroxymethyl)ethyl ester ). Does not bind to CB 1 or CB 2 cannabinoid receptors, but potentiates the apparent binding of 2-AG and increases its ability to inhibit adenylyl cyclase. Enhances in vivo cannabinoid effects of 2-AG following combined administration with 2-linoleoylglycerol.

InChI:InChI=1/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-18(16-20)17-21/h18,20-21H,2-17H2,1H3

Upstream product

• 57-10-3 1-hexadecylcarboxylic acid 
• 56-81-5 glycerol 
• 56599-87-2 2-O-palmitoyl-1,3-O-benzylideneglycerol 
• 305847-08-9 rac-1-monopalmitoylglycerol 
• 150-46-9 triethyl borate 
• 13460-50-9 metaboric acid 
• 10588-87-1 cis-hexadecanoic acid 2-phenyl-1,3-dioxan-5-yl ester 
• 112-39-0 hexadecanoic acid methyl ester 
• 101036-66-2 1,3-dibutyryl-2-palmitoylglycerol 
• 555-44-2 glyceroltripalmitate 

Downstream Products

• 103959-72-4 2-palmitoylglycerol 1,3-bis<3-(3-amino-2,4,6-triiodophenyl)propionate> 
• 103959-71-3 2-palmitoylglycerol 1,3-bis<3-(3-amino-2,4,6-triiodophenyl)acetate> 
• 104013-73-2 palmitoylglycerol 1,3-bis<17-(3-amino-2,4,6-triiodophenyl)heptadecanoate> 
• 1716-07-0 1,3-dioleoyl-2-palmitoylglycerol 
• 3331-34-8 1-oleoyl-2-palmitoyl-rac-glycerol 
• 142-91-6 palmitic acid isopropyl ester 
• 572920-43-5 1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycerol 
• 1487-51-0 1-O-benzyl-3-O-palmitoyl-rac-glycerol 
• 22128-35-4 1-O-benzyl-2-O-palmitoyl-rac-glycerol 
• 65266-83-3 Hexadecanoic acid 2-(toluene-4-sulfonyloxy)-1-(toluene-4-sulfonyloxymethyl)-ethyl ester 
• 572920-49-1 1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycero-3-phosphocholine 
• 572920-36-6 1-O-benzyl-2-O-palmitoyl-rac-glycero-3-phosphocholine 
• 572920-56-0 1-O-benzyl-3-O-palmitoyl-rac-glycero-2-phosphocholine 
• 17364-18-0 1-palmitoyllysophosphatidylcholine 

Relevant articles and documents

Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides

Structured triglycerides of the ABA-type, containing one type of fatty acid (A) in the sn-1 and sn-3 positions and a second type of fatty acid (B) in the sn-2 position of the glycerol, were synthesized using lipases. The highest yields and purities were achieved in a two-step process, where a triglyceride of the B-type was subjected to an alcoholysis reaction in an organic solvent catalyzed by sn-1,3-regiospecific lipases yielding the corresponding 2-monoglyceride (2-MG). Using this strategy, e.g., 2-monopalmitin (2-MP) was obtained in up to 88% yield at >95% purity by crystallization. Esterification of 2-MP with oleic acid resulted in the formation of 1,3-oleyl-2-palmitoyl-glycerol in up to 72% yield containing 94% palmitic acid in the sn-2 position. The best lipases were from Rhizomucor miehei, Rhizopus delemar, and Rhizopus javanicus. Water activity, solvent, and carrier for lipase immobilization strongly influenced the yield and purity of the products in both steps. Furthermore, 2-MG from fish oil were produced by alcoholysis in up to 84% yield at >95% purity.

Monomyristin and monopalmitin derivatives: Synthesis and evaluation as potential antibacterial and antifungal agents

In the present work, monoacylglycerol derivatives, i.e., 1-monomyristin, 2-monomyristin, and 2-monopalmitin were successfully prepared from commercially available myristic acid and palmitic acid. The 1-monomyristin compound was prepared through a transesterification reaction between ethyl myristate and 1,2-O-isopropylidene glycerol, which was obtained from the protection of glycerol with acetone, then followed by deprotection using Amberlyst-15. On the other hand, 2-monoacylglycerol derivatives were prepared through enzymatic hydrolysis of triglycerides in the presence of Thermomyces lanuginosa lipase enzymes. The synthesized products were analyzed using fourier transform infrared (FTIR) spectrophotometer, gas or liquid chromatography-mass spectrometer (GC-MS or LC-MS), and proton and carbon nuclear magnetic resonance (1H- and13C-NMR) spectrometers. It was found that monomyristin showed high antibacterial and antifungal activities, while 2-monopalmitin did not show any activity at all. The 1-monomyristin compound showed higher antibacterial activity against Staphylococcus aureus and Aggregatibacter actinomycetemcomitans and also higher antifungal activity against Candida albicans compared to the positive control. Meanwhile, 2-monomyristin showed high antibacterial activity against Escherichia coli. The effect of the acyl position and carbon chains towards antibacterial and antifungal activities was discussed.

METHOD FOR PREPARING AND PRESERVING SANITIZED PRODUCTS

Described herein are methods of sanitizing and preserving produce and other agricultural products, for example for consumption as Ready-to-Eat. The methods can comprise treating the products with a sanitizing agent and forming a protective coating over the products.

PLANT EXTRACT COMPOSITIONS AND METHODS OF PREPARATION THEREOF

Embodiments described herein relate generally to plant extract compositions and methods to isolate cutin-derived monomers, oligomers, and mixtures thereof for application in agricultural coating formulations, and in particular, to methods of preparing pla