7091-44-3

Usage

Uses

Used in Pharmaceutical Industry:
L-A-PHOSPHATIDIC ACID, DIPALMITOYLFREE ACID is used as a key component in the formulation of liposomes for drug delivery. Its amphiphilic nature allows it to form bilayer structures, which can encapsulate and protect therapeutic agents, enhancing their stability, solubility, and bioavailability.
Used in Cosmetic Industry:
In the cosmetic industry, L-A-PHOSPHATIDIC ACID, DIPALMITOYLFREE ACID is used as an emollient and skin conditioning agent. Its ability to form lipid bilayers helps to maintain the skin's natural barrier function, providing moisturization and protection against environmental stressors.
Used in Food Industry:
L-A-PHOSPHATIDIC ACID, DIPALMITOYLFREE ACID is used in the food industry as an emulsifier and stabilizer. Its amphiphilic properties enable it to improve the texture, appearance, and shelf life of various food products by reducing the tendency of ingredients to separate.
Used in Research and Development:
In the field of research and development, L-A-PHOSPHATIDIC ACID, DIPALMITOYLFREE ACID is used as a model compound to study the properties and behavior of phospholipids in biological membranes. This helps researchers gain a better understanding of membrane dynamics and the role of phospholipids in cellular processes.

Purification Methods

Recrystallise the acid from Me2CO at low temperature. At 21o it is soluble in *C6H6 (4.2%), pet ether (0.01%), MeOH (2%), EtOH (2.5%), AcOH (1.3%), Me2CO (1.76%), and Et2O (1.5%). [Baer J Biol Chem 189 235 1951.]

InChI:InChI=1/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1

Upstream product

• 30334-71-5 1,2-dipalmitoyl-sn-glycerol 
• 909128-73-0 C₄₁H₇₅N₂O₈P 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 3036-82-6 dipalmitoylphosphatidyl-L-serine 
• 71321-85-2 (R)-3-((dichlorophosphoryl)oxy)propane-1,2-dipalmitate 
• 112-67-4 n-hexadecanoyl chloride 
• 30403-51-1 1,2-di-O-hexacecanoyl-3-O-benzyl-sn-glycerol 
• 215322-58-0 (R)-O¹-diphenoxyphosphoryl-O²,O³-dipalmitoyl-glycerol 

Downstream Products

• 80795-00-2 dibenzyl 1,2-dipalmitoyl-sn-glycero-3-phosphate 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 88035-56-7 dibenzyl 2-palmitoyl-sn-glicero-3-phosphate 
• 88035-57-8 1-phospho-2-palmitoyl-(R)-propane-1,2-diol dibenzyl ester 
• 69483-93-8 C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾ 

Relevant academic research and scientific papers

Preparation method of 1,2-dipalmitoyl-SN-glycerol-3-phosphoric acid

The invention discloses a preparation method of 1,3-butanediol. The invention discloses a preparation method of 1,2-dipalmitoyl-SN-glycerol-3-phosphoric acid. The method comprises the following steps:(a) reacting dipalmitin, namely a compound I, in the presence of a solvent and tetrazole; carrying out nucleophilic substitution reaction with bis(diisopropylamino)(2-cyanoethoxy)phosphine, then carrying out reaction with trichloroethanol, and carrying out mCPBA oxidation to obtain (2R)-3-((((2-cyanoethoxy)(2,2,2-trichloroethoxy)phosphoryl)oxy)propane-1,2-dipropionic acid dipropyl ester, namely acompound II; (b) carrying out hydrolysis reaction on the compound II and DBU to obtain (2R)-3-(((hydroxyl(2,2,2-trichloroethoxy)phosphoryl)oxy)propane-1,2-dipropyl dipropionate, namely a compound III; and (c) carrying out hydrolysis reaction on the compound III under the action of acid and zinc powder to obtain the 1,2-dipalmitoyl-SN-glycerol-3-phosphoric acid, namely a compound IV. The method has the characteristics of simplicity and convenience in operation, higher total yield, low pollution, low energy consumption, easiness in separation and purification of products and the like, and is more beneficial to industrial production.

Preparation method of dipalmitoyl phosphatidic acid

The invention provides a method for artificially synthesizing phospholipid dipalmitoyl phosphatidic acid (DPPA), which comprises the following steps: by using 1, 2-dipalmitoyl-sn-glycerol as a raw material, carrying out esterification reaction, carrying out hydrolysis reaction, and dissolving, filtering and recrystallizing the obtained product to obtain high-purity dipalmitoyl phosphatidic acid. The dipalmitoyl phosphatidic acid (DPPA) prepared by the method disclosed by the invention can be used as a pharmaceutic adjuvant for various types of medicines such as lipidosome, emulsifier, capsuleand the like.

Structural characterization of oxidized glycerophosphatidylserine: Evidence of polar head Oxidation

Non-oxidized phosphatidylserine (PS) is known to play a key role in apoptosis but there is considerable research evidence suggesting that oxidized PS also plays a role in this event, leading to the increasing interest in studying PS oxidative modifications. In this work, different PS (1-palmitoyl-2-linoleoyl-sn-glycero-3-phospho-L-serine (PLPS), 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-L-serine (POPS), and 1,2-dipalmitoyl-sn-glycero-3-phospho-L-serine (DPPS) were oxidized in vitro by hydroxyl radical, generated under Fenton reaction conditions, and the reactions were monitored by ESI-MS in negative mode. Oxidation products were then fractionated by thin layer chromatography (TLC) and characterized by tandem mass spectrometry (MS/MS). This approach allowed the identification of hydroxyl, peroxy, and keto derivatives due to oxidation of unsaturated fatty acyl chains. Oxidation products due to oxidation of serine polar head were also identified. These products, with lower molecular weight than the non-modified PS, were identified as [M - 29 - H]- (terminal acetic acid), [M - 30 - H] - (terminal acetamide), [M - 13 - H]- (terminal hydroperoxyacetaldehyde), and [M - 13 - H]- (terminal hydroxyacetaldehyde plus hydroxy fatty acyl chain). Phosphatidic acid was also formed in these conditions. These findings confirm the oxidation of the serine polar head induced by the hydroxyl radical. The identification of these modifications may be a valuable tool to evaluate phosphatidylserine alteration under physiopathologic conditions and also to help understand the biological role of phosphatidylserine oxidation in the apoptotic process and other biological functions. American Society for Mass Spectrometry, 2011.

Synthesis of dehydroepiandrosterone analogues modified with phosphatidic acid moiety

Dehydroepiandrosterone (DHEA) and its metabolite 7α-OH DHEA have many diverse physiological, biological and biochemical effects encompassing various cell types, tissues and organs. In in vitro studies, DHEA analogues have myriad biological actions, but in vivo, especially in oral administration, DHEA produces far more limited clinical effects. One of the possible solutions of this problem is conversion of DHEA to active analogues and/or its transformation into prodrug form. In this article, the studies on the conversion of DHEA and 7α-OH DHEA into their phosphatides by the phosphodiester approach are described. In this esterification, N,N-dicyclohexylcarbodiimide (DCC) was the most efficient coupling agent as well as p-toluenesulphonyl chloride (TsCl).

A new approach to phospholipid synthesis using tetrahydropyranyl glycerol: Rapid access to phosphatidic acid and phosphatidylcholine, including mixed-chain glycerophospholipid derivatives

Phospholipid synthesis using tetrahydropyranyl glycerol was investigated to produce chiral diglycerides, phosphorylated, and target phospholipid compounds. The synthetic compounds were used for the establishment of structure activity relationships with respect to phospholipid-phospholipid and phospholipid-protein interactions. The synthesis involves regioselective incorporation of three different substituents at the three glycerol positions that normally requires the use of multiple protecting groups. An efficient general route to phosphatidylcholine and phosphatidic acid is applicable to the preparation of a wide range of structurally related glycerophospholipid derivatives. The investigation resulted a facile and efficient method for the preparation of a wide range of diacylglycerols and phospholipids, including phospholipid acid, symmetric and mixed chain phosphatidylcholines.

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.