19698-29-4

Basic information

• Product Name: 2,3-bis(palmitoyloxy)propyl dihydrogen phosphate
• Synonyms: Dipalmitoylphosphatidic acid; 2,3-Bis(palmitoyloxy)propyl dihydrogen phosphate; Palmitin, 1,2-di-, dihydrogen phosphate
• CAS NO: 19698-29-4
• Molecular Formula: C₃₅H₆₉O₈P
• Molecular Weight: 648.896
• EINECS: 243-238-2
• Mol File: 19698-29-4.mol

Chemical Properties

• CAS DataBase Reference: 2,3-bis(palmitoyloxy)propyl dihydrogen phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-bis(palmitoyloxy)propyl dihydrogen phosphate(19698-29-4)
• EPA Substance Registry System: 2,3-bis(palmitoyloxy)propyl dihydrogen phosphate(19698-29-4)

Safety Data

• Hazardous Substances Data: 19698-29-4(Hazardous Substances Data)

Usage

Uses

Used in Skincare and Cosmetic Industry:
2,3-Bis(palmitoyloxy)propyl dihydrogen phosphate is used as an emulsifier for improving the texture and spreadability of skincare formulations. It helps in creating a stable blend of ingredients, ensuring a smooth and even application on the skin.
2,3-Bis(palmitoyloxy)propyl dihydrogen phosphate is used as a surfactant for enhancing the performance of personal care products. It aids in the dispersion of oils and other ingredients, providing a more effective delivery of active components to the skin.
2,3-Bis(palmitoyloxy)propyl dihydrogen phosphate is used as a moisturizing agent for providing hydration and protective benefits to the skin. It helps to maintain the skin's natural moisture balance, preventing dryness and promoting a healthy skin appearance.
2,3-Bis(palmitoyloxy)propyl dihydrogen phosphate is used as an emollient for softening and smoothing the skin. Its emollient properties contribute to the overall feel and texture of moisturizers and lotions, making it a popular ingredient in various personal care products.

Upstream product

• 57-03-4 lysophosphatidic acid 
• 623-65-4 palmitic anhydride 
• 112-67-4 n-hexadecanoyl chloride 
• 69176-47-2 1,2-di-O-palmitoyl-3-O-benzyl-rac-glycerol 
• 75257-03-3 Hexadecanoic acid 2-(bis-benzyloxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester 
• 75257-06-6 phosphoric acid dibenzyl ester-(2,3-bis-palmitoyloxy-propyl ester) 
• 2644-64-6 1,2-dipalmitoyl-rac-glycero-3-phosphatidylcholine 
• 158268-08-7 rac-1,2-dipalmitoylglycero-3-phosphodichloride 
• 75257-10-2 phosphoric acid benzyl ester-(2,3-bis-palmitoyloxy-propyl ester) 
• 1042289-75-7 rac-1,2-dipalmitoylglycerol 
• 60831-48-3 Hexadecanoic acid 2-[bis-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 76189-96-3 diphenyl 1,2-di-O-palmitoyl-rac-3-glycerophosphate 

Downstream Products

• 112-39-0 hexadecanoic acid methyl ester 
• 22002-85-3 1-Palmitoyl-lysophosphatidic acid 
• 4537-77-3 dipalmitoylphosphatidylglycerol 
• 115290-76-1 C₄₄H₇₉N₃O₁₅P₂^(2-)*2Na⁽¹⁺⁾ 
• 91859-07-3 1-(1,2-dipalmitoyl-sn-glycero-3-phospho)-2-O-benzyl-rac-glycerol 
• 92075-63-3 1,3-di(1,2-dipalmitoyl-sn-glycero-3-phospho)-2-O-benzylglycerol 

Relevant articles and documents

Influence of model membrane structure on phospholipase D activity

Phospholipase D (PLD) catalyzes the hydrolysis of 1,2-dipalmitoylphosphatidylcholine (DPPC) to 1,2-dipalmitoylphosphatidic acid (DPPA). The influence of substrate (DPPC) structure on the efficiency and rate of the hydrolysis reaction has been investigated in monolayers by grazing incidence X-ray diffraction (GIXD) and polarization-modulated infrared reflection absorption spectroscopy (PM-IRRAS). Spectroscopic analysis of the phosphate groups provides a quantitative estimation of the hydrolysis efficiency. It was found that the PLD activity depends on the substrate structure and exhibits a maximum in the more disordered liquid-expanded phase. Different mixtures of DPPC and DPPA were investigated by GIXD. Phase separation and the presence of two types of condensed phase domains (DPPC-rich and DPPA-rich) were observed. Higher DPPA concentrations inhibit the hydrolysis reaction. The inhibiting DPPA concentration is a function of the monolayer pressure. The inhibition effect of the hydrolysis product depends on the microstructure of the DPPC-rich domains. The tilt angle in DPPC-rich domains decreases with increasing DPPA amount. Such structural changes could be an indication of essential conformational changes in the head group region, which could therefore reduce the accessibility of the POC bond for a PLD attack.

BIOPASSIVATING MEMBRANE STABILIZATION BY MEANS OF NITROCARBOXYLIC ACID-CONTAINING PHOSPHOLIPIDS IN PREPARATIONS AND COATINGS

The present invention relates to nitro-carboxylic acid (s)-containing phospholipids, to be used for coating of medical devices such as stents, catheter balloons, wound pads or surgical suture material and for bio-passivating compositions, such as rinses, waterproofing solutions, coating solutions, cryoprotection solutions, cold preservation media, lyoprotection solutions, contrast media solutions, preservation and reperfusion solutions containing these compounds as well as preparing solutions thereof and coating medical devices as well as their uses.

CARBOXYLATED PHOSPHATIDIC ACID ESTERS

Novel compounds of formula in which R1 and R2 are phospholipid fatty acid residues and A is an aliphatic and/or cycloaliphatic hydrocarbon chain optionally substituted by hydroxy and/or further carboxylic functions. The novel compounds are useful for making liposomes of enhanced stability and entrapping capacity.

Preparative synthesis of 1,2- and 1,3-disubstituted phosphatidic acids

A general preparative method for the synthesis of 1,2(3)-diacyl and 1-alkyl-2(3)-acyl phosphatidic acids by examples with acyl = C15H31CO and alkyl = C16H33 was proposed. The procedure involved two stages: the interaction of 1,2- or 1,3-disubstituted glycerols with POCl3 at 0-3°C leading to the corresponding phosphodichlorides, and their hydrolysis with 80% aqueous DMSO or DMF at room temperature. The corresponding phosphatidic acids were isolated in the form of pyridinium salts in approximately 80% yields. In the absence of DMSO or DMF, the hydrolysis of 1-hexadecyl-2-palmitoyl 3-glycerophosphodichloride with aqueous pyridine resulted in an admixture of P,P′-bis(1-hexadecyl-2-palmitoyl)-3-glyceryl pyrophosphate (10-30 mol %) along with the corresponding phosphatidic acid. This admixture also yielded the target phosphatidic acid upon hydrolysis in aqueous DMSO. 1999 MAEe Cyrillic signK "Hayκa/Interperiodica".

Synthesis of liponucleotides

A process for the preparation of glycerol di- or triphosphate derivatives comprising coupling the phosphate group of a glycerol monophosphate derivative in which one of the phosphate hydroxyls is replaced by a leaving group, with the terminal phosphate group of a mono- or diphosphate compound or a salt thereof, in the presence of a basic catalyst, under anhydrous conditions.

Composition and method for treatment of disseminated fungal infections in mammals

A method is disclosed for treatment of disseminated fungal infection in a mammal comprising the administration of a fungicidally effective amount of Amphotericin B encapsulated in a substantially sterol-free liposome to the infected mammal. Also provided is an agent for treatment of disseminated fungal infection in a mammal comprising Amphotericin B encapsulated in a liposome which consists essentially of lipids other than sterols.

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.

Acoustic shock wave targeting of drug delivery in patients

Acoustic shock waves generated outside a patient's body are focused upon selected target zones within a patient's body to cause release of biologically active substances from liposomes administered to the patient. The procedures may serve to increase cell uptake of drugs and reduce systemic toxicity.

A new approach to the synthesis of phosphatidic acids and their analogs

The synthesis of phosphatidic acids, their monoamides and dialkyl esters, and thiophosphatidic acids was realized on the basis of the amidophosphites of 1,2-diacylglycerols and 1,2-isopropylideneglycerol.