69176-47-2

Usage

Uses

Used in Pharmaceutical Industry:
1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL is used as a precursor for the synthesis of glycerophospholipid derivatives, which serve as antioxidants and lipid peroxide inhibitors. These derivatives play a crucial role in protecting cells from oxidative damage and maintaining cellular integrity, making them valuable in the development of pharmaceutical agents for various health conditions.
Used in Cosmetic Industry:
In the cosmetic industry, 1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL and its derivatives are utilized for their antioxidant and lipid peroxide inhibitory properties. These properties help in maintaining the stability and effectiveness of cosmetic products, as well as providing skin protection against environmental stressors and promoting overall skin health.
Used in Food Industry:
1,2-DIPALMITOYL-3-O-BENZYL-RAC-GLYCEROL and its glycerophospholipid derivatives can be used in the food industry as natural antioxidants and preservatives. They help in extending the shelf life of food products by inhibiting the formation of lipid peroxides, which can lead to rancidity and spoilage. Additionally, these compounds can contribute to the overall quality and safety of food products.

Upstream product

• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 112-67-4 n-hexadecanoyl chloride 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 1487-51-0 1-O-benzyl-3-O-palmitoyl-rac-glycerol 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 2930-05-4 Benzyloxymethyl-oxiran 
• 57-10-3 1-hexadecylcarboxylic acid 

Downstream Products

• 3036-84-8 Hexadecanoic acid 2-[((S)-2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-phenoxy-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 115290-76-1 C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾ 
• 19698-29-4 1,2-Dipalmitoylphosphatidic acid 
• 176776-97-9 Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester 
• 148286-68-4 (2-Chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate 

Relevant academic research and scientific papers

Studies on the synthesis of dehydroepiandrosterone (DHEA) phosphatide

Synthetic dehydroepiandrosterone (DHEA) phosphatide 1c, (R = C15H31), was prepared by three methods. The most efficient of these involved the coupling of the commercially available DHEA 1a and commercially available phosphatidic acid

Preparation of benzothiazolyl-decorated nanoliposomes

Amyloid β (Aβ) species are considered as potential targets for the development of diagnostics/therapeutics towards Alzheimer’s disease (AD). Nanoliposomes which are decorated with molecules having high affinity for Aβ species may be considered as potential carriers for AD theragnostics. Herein, benzothiazolyl (BTH) decorated nanoliposomes were prepared for the first time, after synthesis of a lipidic BTH derivative (lipid-BTH). The synthetic pathway included acylation of bis(2-aminophenyl) disulfide with palmitic acid or palmitoyl chloride and subsequent reduction of the oxidized dithiol derivative. The liberated thiols were able to cyclize to the corresponding benzothiazolyl derivatives only after acidification of the reaction mixture. Each step of the procedure was monitored by HPLC analysis in order to identify all the important parameters for the formation of the BTH-group. Finally, the optimal methodology was identified, and was applied for the synthesis of the lipid-BTH derivative. BTH-decorated nanoliposomes were then prepared and characterized for physicochemical properties (size distribution, surface charge, physical stability, and membrane integrity during incubation in presence of buffer and plasma proteins). Pegylated BTH-nanoliposomes were demonstrated to have high integrity in the presence of proteins (in comparison to non-peglated ones) justifying their further exploitation as potential theragnostic systems for AD.

Synthetic method of alkynyl-modified phospholipid derivative for preparing functional phospholipid giant vesicle

The invention discloses a synthetic method of an alkynyl-modified phospholipid derivative for preparing a functional phospholipid giant vesicle. The method comprises the following steps: with solketalas a starting raw material, selectively introducing an alkyl chain through benzyl protection, deprotection and DCC-DMAP catalytic condensation, synthesizing 3-hydroxy-1,2- dipalmitin, using 2-chloro-2-oxo-1,3,2-dioxaphospholane as a phosphorylation reagent, carrying out ring opening reaction by using 1-dimethylamine-2-allylene, and preparing the alkynyl-modified phospholipid derivative. The method is simple in synthetic route, a highly toxic reagent does not need to be used, and the phospholipid giant vesicle with an adjustable surface reactivity group density can be prepared by mixing the obtained alkynyl-modified phospholipid derivative and common phospholipid available in the market according to a certain proportion. The possibility is provided for the further stabilization and functionalization of this type of the vesicle.

COMPOSITIONS AND METHODS FOR DELIVERY OF THERAPEUTIC AGENTS

This disclosure provides improved lipid-based compositions, including lipid nanoparticle compositions, and methods of use thereof for delivering agents in vivo including nucleic acids and proteins. These compositions are not subject to accelerated blood clearance and they have an improved toxicity profile in vivo.

[F-18]labeiing of 1,2-diacylglycerols

We have developed two kinds of [18F]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(ω-[18F]fluoroacyl)-2-acylglycerols (1*,2-[18F]FDAGs) and 2-(ω[18F]fluoroacyl)-1-acylglycerols (1,2*-[18F]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[18F]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with ω-[18F]fluoroacyl chlorides (method A) and 1-(16-[18F]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C16,C16)) and 1-(8-[18F]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[18F]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[18F]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(ω-[18F]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(ω-bromoacyl)-1-acylglycerol with [18F]F- (method B) and 2-(16-[18F]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C16)) and 2-(8-[18F]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[18F]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[18F]FDAGs were obtained in radiochemical yields of 8-35% (based on [18F]F-) with radiochemical purities of > 97% and the purified 1,2*-[18F]FDAGs were in radiochemical yields of 5-15% with radiochemical purities of > 95%. The total synthesis time from the start of the reactive [18F]F- production, including HPLC purification, was 100-135 min (method A) and 115-175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[18F]FDAG(C16,C16), 1*,2-[18F]FDAG (C8,C16), and 1,2*-[18F]FDAG(C16,C16), 1,2*-[18F]FDAG(C16,C8) for animal studies.

Synthesis of liposomal phospholipid-(N4-palmitoyl-1-β-D-arabinofuranosylcytosine) conjugates and evaluation of their cytostatic activity against L1210 murine leukemia

N4-Palmitoyl-araC, a prodrug of the cytostatic compound 1-β-D-arabinofuranosylcytosine (araC), was linked by means of the triester method to the phospholipids (2-chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate, (2-chlorophenyl) (1,2-di-O-octadecylglyceryl) phosphate and (2-chlorophenyl) (1-O-octadecyl-2-O-palmitoylglyceryl) phosphate. In the first step of these gram-scale syntheses phospholipid-(N4-palmitoyl-araC) conjugates were obtained the linkage of which was accomplished via a triester group. In the second step the final condensates were obtained through transformation of the triester into a diester linkage by removal of the 2-chlorophenyl group. The cytostatic activity of these compounds which form stable liposomal preparations together with matrix lipids was evaluated according to the L1210 mouse leukemia model. The conjugates containing a triester linkage were shown to be ineffective, whereas those with a diester linkage display a significantly higher antitumor activity as compared to N4-palmitoyl-araC and araC. With the diester 6a-8a 80-100% of the treated animals were cured at a total dose of 200 μmol/kg, whereas with araC given at a fourfould higher concentration none of the treated mice survived. VCH Verlagsgesellschaft mbH, 1996.

Phospholipid derivatives

Phospholipid derivatives resulting from coupling of ascorbic acid to a glycerol ester or ether via a phosphoric acid residue and having antioxidant activity and lipid peroxide inhibiting activity, which have the formula STR1 wherein R1 and R2 represent the same or different and each represents an alkyl or acyl group and neither formula represents any particular configuration nor conformation.

A GENERAL PROTOCOL FOR THE PREPARATION OF PHOSPHOLIPIDS VIA PHOSPHITE COUPLING

A method for the facile preparation of a variety of phospholipids and their derivatives has been developed that utilizes a highly efficient phosphite coupling procedure for the synthesis of a phosphite triester, which may then be readily transformed into the corresponding phosphate diester by sequential oxidation and O-deprotection.

Nucleoside conjugates. 10. Synthesis and antitumor activity of 1-β-D-arabinofuranosylcytosine 5'-diphosphate-1,2-dipalmitins

Three 1-β-D-arabinofuranosylcytosine 5'-diphosphate-1,2-dipalmitins from L-, D- and DL-α-dipalmitoylphosphatidic acids have been synthesized and their antitumor activity against two ara-C2 resistant L1210 lymphoid leukemia sublines in mice were evaluated. These new prodrugs of ara-C include ara-CDP-L-dipalmitin (1), ara-CDP-D-dipalmitin (2), and ara-CDP-DL-dipalmitin (3). The L and DL isomers produced significant increase in life span (>400%) and four to five long-term survivors (>45 days) out of six animals bearing ip implanted partially ara-C resistant L1210 subline [L1210/ara-C (I)], while the D isomer displayed a marginal activity (ILS 100-121%). In contrast, the L isomer was completely ineffective against deoxycytidine kinase deficient ara-C resistant L1210 subline [L1210/ara-C (II)]. However, the results demonstrate that the L and DL isomers of ara-CDP-dipalmitin are promising new prodrugs of ara-C with improved efficacy.