68737-67-7

Basic information

• Product Name: (Z,Z)-()-(7-oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide
• Synonyms: (Z,Z)-(1)-(7-Oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide; 2,3-bis[(9Z)-octadec-9-enoyloxy]propyl 2-(trimethylammonio)ethyl phosphate
• CAS NO: 68737-67-7
• Molecular Formula: C₄₄H₈₄NO₈P
• Molecular Weight: 786.1134
• EINECS: 272-114-0
• Mol File: 68737-67-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (Z,Z)-()-(7-oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (Z,Z)-()-(7-oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide(68737-67-7)
• EPA Substance Registry System: (Z,Z)-()-(7-oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide(68737-67-7)

Safety Data

• Hazardous Substances Data: 68737-67-7(Hazardous Substances Data)

Usage

General Description

(Z,Z)-()-(7-oleoyl-4-oxido-10-oxo-3,5,9-trioxa-4-phosphaheptacos-18-enyl)trimethylammonium 4-oxide, also known as OTAC, is a synthetic cationic surfactant with a long hydrophobic tail and a positively charged quaternary ammonium head group. It is commonly used as an emulsifier and dispersant in various industrial and household products, including fabric softeners, hair conditioners, and cleaning agents. OTAC is known for its ability to reduce surface tension, enhance wetting and spreading, and stabilize emulsions. Additionally, it has antimicrobial properties and is used in some personal care products as a preservative. OTAC is considered a safe and effective ingredient when used in accordance with regulations and guidelines for cosmetic and household product formulations.

Upstream product

• 2442-61-7 1,2-dioleoylglycerol 
• 55357-38-5 choline tosylate 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 18175-45-6 Tras-Elaidate sodium salt 
• 4235-95-4 dioleoylphosphatidylcholine 
• 112-80-1 cis-Octadecenoic acid 

Downstream Products

• 62-49-7 choline 
• 108824-18-6 (E)-Octadec-9-enoic acid (R)-2-[((S)-3-amino-3-carboxy-propoxy)-hydroxy-phosphoryloxy]-1-((E)-octadec-9-enoyloxymethyl)-ethyl ester 
• 22002-87-5 1-oleoyl-2-lyso-sn-glycero-3-phosphate 
• 112-62-9 Methyl oleate 
• 138630-87-2 N-<4-nitro-1-(benzoyloxy)-3-benzyl>-1,2-dioleoylphosphatidylcholine 
• 87803-75-6 N,N-dimethyl-1,2-dioleoylphosphatidylethanolamine 

Relevant articles and documents

Method for preparing difatty acyl phosphatidylcholine by solid-phase reaction

The invention relates to a method for preparing difatty acyl phosphatidylcholine by a solid-phase reaction. Glycerol phosphatidylcholine is subjected to wet-process loading by using a high-activity solid adsorbent, and then a condensation reaction is carried out on the glycerol phosphatidylcholine with fatty acid to obtain the difatty acyl phosphatidylcholine. The method comprises the following steps: dissolving glyceryl phosphatidylcholine in an organic solvent, adding a high-activity solid adsorbent, carrying out adsorbing dispersion while stirring, removing the organic solvent by vacuum evaporation, and carrying out vacuum drying on the obtained solid-phase loaded mixed material; dissolving fatty acid in an organic solvent, adding a condensation coupling agent, carrying out heating reflux to prepare active ester of fatty acid, adding the solid-phase loaded glyceryl phosphatidylcholine, and continuing reflux to prepare a difatty acyl phosphatidylcholine crude product; and carrying out filtering to recover the high-activity solid adsorbent, desolventizing mother liquor, pulping a crude product by using an organic solvent, and carrying out recrystallizing to obtain the high-puritydifatty acyl phosphatidylcholine. According to the method, the reaction yield reaches 65% or above, the product purity reaches 99% or above, the process is simple, the production period is short, andindustrial production is easy to achieve.

cis-trans Isomerization of monounsaturated fatty acid residues in phospholipids by thiyl radicals

Thiyl radicals reversibly attack the double bonds of methyl oleate and dioleoyl phosphatidyl choline (DOPC), thus producing methyl elaidate and the corresponding phospholipids containing trans-fatty acid residues in high yield. These processes are radical chain reactions with relatively long chain lengths. The rate constant for the β-elimination of a thiyl radical from the adduct radical has been estimated to be 6 x 106 s-1 at ambient temperature. The cis-trans isomerization of fatty acid residues in DOPC vesicles (multilamellar vesicles and large unilamellar vesicles made by the extrusion technique) by a thiyl radical, generated from biologically relevant thiols, has also been studied in detail. The presence of 0.2 mM oxygen does not influence the effectiveness of cis-trans isomerization in both homogeneous solution and lipid vesicles. This process, which does not cause lipid degradation but permanent modification of the membrane constituents, ultimately influences the barrier properties and functions of biological membranes.