7091-44-3

Basic information

• Product Name: L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID
• Synonyms: L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID;1,2-dipalmitoyl-sn-glycero-3-phospha-tidic acid;L-A-phosphatidic acid;(1R)-1-[(phosphonooxy)methyl]-1,2-ethanediyl ester Hexadecanoic acid;[R,(+)]-1-O,2-O-Dipalmitoyl-L-glycerol 3-phosphoric acid;1-O,2-O-Dihexadecanoyl-L-glycerol-3-phosphoric acid;1-O,2-O-Dipalmitoyl-L-glycerol phosphoric acid;1-O,2-O-Dipalmitoyl-L-glycerol-3-phosphoric acid
• CAS NO: 7091-44-3
• Molecular Formula: C₃₅H₆₉O₈P
• Molecular Weight: 648.89
• Mol File: 7091-44-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 706.9°C at 760 mmHg
• Flash Point: 381.3°C
• Appearance: /
• Density: 1.015g/cm³
• Vapor Pressure: 7.15E-22mmHg at 25°C
• Refractive Index: 1.473
• Storage Temp.: ?20°C
• CAS DataBase Reference: L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID(CAS DataBase Reference)
• NIST Chemistry Reference: L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID(7091-44-3)
• EPA Substance Registry System: L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID(7091-44-3)

Safety Data

• Hazardous Substances Data: 7091-44-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A 1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate in which the 1-acyl group is also hexadecanoyl.

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

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

Downstream Products

• 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⁺⁾ 
• 63-89-8 L-dipalmitoylphosphatidylcholine 
• 80795-00-2 dibenzyl 1,2-dipalmitoyl-sn-glycero-3-phosphate 

Relevant articles and documents

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.

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.

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.