14617-86-8

Usage

Uses

Used in Waste Paper Deinking Industry:
P-NITROPHENYL STEARATE is used as a substrate for the method of carrying out waste paper deinking using the bifunctional fusion enzyme Lip-EG1CD. This application aids in the efficient removal of ink from recycled paper, contributing to a more sustainable and environmentally friendly paper recycling process.
Used in Enzyme Research and Analysis:
P-NITROPHENYL STEARATE is used as a substrate in the study and analysis of lipase enzymes. Its ability to produce a yellow-colored product upon enzymatic hydrolysis makes it a valuable tool for monitoring enzyme activity, allowing researchers to better understand the function and efficiency of these enzymes in various biological processes.
Used in Pharmaceutical and Cosmetic Industries:
P-NITROPHENYL STEARATE may also find applications in the pharmaceutical and cosmetic industries, where lipases are often involved in the synthesis of various compounds or the breakdown of fats and oils. By using P-NITROPHENYL STEARATE as a substrate, researchers can study the activity and specificity of lipases, leading to the development of more effective drugs and cosmetic products.

InChI:InChI=1/C24H39NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(26)29-23-20-18-22(19-21-23)25(27)28/h18-21H,2-17H2,1H3

Upstream product

• 100-02-7 4-nitro-phenol 
• 112-76-5 Stearoyl chloride 
• 57-11-4 stearic acid 
• 7693-46-1 4-Nitrophenyl chloroformate 

Downstream Products

• 103931-03-9 (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol 
• 103931-04-0 L-threo-3-0-(diphenyl-t-butylsylil)-2-N-stearoylsphingosine 
• 21400-91-9 N-stearoyl-L-tryptophan 
• 184648-99-5 Octadecanoic acid [(R)-2-(4-methoxy-phenoxy)-1-(octadecanoylamino-methyl)-ethyl]-amide 
• 41106-92-7 (2S,3R,4E)-3-O-benzoyl-2-octadecanamido-4-octadecene-1,3-diol 
• 299172-56-8 3-O-benzoyl-1-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N-stearoyl-D-erythro-sphingosine 
• 164988-80-1 Octadecanoic acid [(E)-(1S,2R)-2-hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-heptadec-3-enyl]-amide 
• 54336-64-0 (2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol 
• 58909-84-5 sphingomyelin 
• 104012-20-6 Diisopropyl-phosphoramidous acid (E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester 
• 103931-05-1 Diisopropyl-phosphoramidous acid (E)-(2S,3S)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester 
• 115523-50-7 C₅₇H₁₀₁N₂O₆PSi 
• 115523-51-8 C₅₇H₁₀₁N₂O₆PSi 
• 103931-10-8 C₅₇H₁₀₁N₂O₅PSSi 

Relevant academic research and scientific papers

Selective Decarbonylation of Fatty Acid Esters to Linear α-Olefins

Selective decarbonylation of p-nitrophenol esters of fatty acids to the corresponding linear α-olefins (LAOs) was achieved using palladium catalysis. After extensive ligand screening, a mixed-ligand system exploiting the trans-spanning diphosphine XantPhos and an N-heterocyclic carbene (IPr) was identified as the most effective in yielding high α-selectivity and high conversions of the ester (>98% selectivity, >90% conversion using 2.5 mol % of PdCl2 and 5 mol % of the ligands, 190 °C, 2-2.5 h). On the basis of insights from modeling at the density functional level of theory, we propose that the mixed-ligand set achieves high α-selectivity by promoting olefin dissociation from the palladium center following β-hydride elimination, which is especially facilitated both by the combined steric bias of the mixed-ligand set and by the ability of the XantPhos ligand to coordinate in both mono- and bidentate fashions.

Esterification of free fatty acids (Biodiesel) using nano sulfated-titania as catalyst in solvent-free conditions

Nano sulfated titania was tested as catalyst for esterification of free fatty acids, specially methanolic and ethanolic esterification of stearic acid (biodiesels). Factorial design evidenced a positive effect of reaction temperature, amount of catalyst, and solvents on ester conversion. This nano-sized sulfated titania has been prepared by a sol-gel hydrothermal process. This prepared sulfated titania showed high catalytic activity in direct esterification of fatty acids as well as benzoic acids with various alcohols and phenols under solvent-free conditions. This method is of great value because of its environmentally benign character, easy handling, high yields, convenient operation, and green. FT-IR studies are shown that the catalyst can be reused for acylation without loss of catalytic activity.

Fingerprint lipolytic enzymes with chromogenic p-nitrophenyl esters of structurally diverse carboxylic acids

A series of structurally diverse chromogenic esters, including a new compound (4-nitrophenyl 2-methylpentanoate), has been synthesized, constituting an array of 17 substrates which could be applied to rapidly fingerprint the activity of lipases or esterases to reveal their substrates specificity and functional characteristics. Combined with genetic technology such as "data mining" and directed evolution, such fingerprints might be a promising platform for discovery of potentially useful enzymes in industrial application. The fingerprint of commercially available Lipase-B from Candida antarctica as a model enzyme was first measured to confirm the reliability of this method. Then three new enzymes mined from genomic libraries were successfully fingerprinted, revealing the functional characteristics of those enzymes. Among them, the enzyme SrfAD was founded with specific substrate preference towards cycloalkyl carboxylic esters and aromatic esters, making it more promising in synthetic utilities than other tested enzymes.

HIGHER N-ACYL-L-AMINO ACID DERIVATIVES

A preparative method is proposed for obtaining higher N-acylamino acids by reaction of free amino acids with fatty acid nitrophenyl esters.It was shown that these acids can transport positive ions through a liquid lipophilic medium.A direct method is proposed for obtaining fatty acid 4-nitrophenyl esters by boiling 4-nitrophenol and the fatty acid in xylene in a Soxhlet apparatus in the presence of an acid catalyst.

Synthesis and Spectral Properties of Chemically and Stereochemically Homogeneous Sphingomyelin and its Analogues

2-N-Stearoylspingosyl-1-phosphocholines of D-erythro (2S,3R) and L-threo (2S,3S) configurations and their phosphorothioyl analogues were obtained by a purely synthetic approarch using O-methyl-N,N-di-isopropylaminophosphorochloridite as the phosphitylating reagent for the formation of the phophodiester linkage.Final products were obtained pure in yields of 70-75 percent.The structure and the purity of synthesized compounds was determined using 1H, 13C, and 31P n.m.r. spectroscopy.With respect to the structure of the sphingosine long-chain base the synthetic D-erythro-SPM was found to be identical with the natural sphigomyelin from bovine brain whereas the semisynthetic N-palmitoylshingomyelin obtained via a deacylation-reacylation pathway comprises a mixture of D-erythro- and L-thero-SPM.The phosphorothioyl analogues of sphingomyelin synthesized by addition of elementar sulphur to intermediate phosphite were separated into individual diastereomers having opposite configuration at phosphorus.The absolute configurations of diastereomers at phosphorus were assigned based on the known stereospecifity of phospholipase C in the hydrolysis of phosphorothioyl analogues of phospholipids.1H N.m.r. data of synthesized compounds suggest that the configuration at C-3 of the sphingosine influences the average conformation of sphingomyelin with respect to the angle of rotation about the C(1)-C(2) bond.

CHIMIE DES SUCRES SANS GROUPEMENTS PROTECTEURS-I-ESTERIFICATION REGIOSELECTIVE DE L'HYDROXYLE ANOMERE DU LACTOSE, DU MALTOSE ET DU GLUCOSE

Treatment of acyl chlorides 4 with mercaptothiazoline, mercaptobenzothiazole, p-nitrophenol and 8-hydroxyquinoline in the presence of Et3N, afforded high yields of the corresponding reactive amides 5a-h,S-thioesters 6e-h and aryl esters 7e-h and 8a-h, respectively.The esters 6e-h, 7e-h and 8e-h reacted with excess β-lactose in pyridine, to give the corresponding β-esters 9e-h resulting from esterification of the anomeric hydroxyl of the sugar.The amides 5c, f-h gave the α-lactosyl esters 9c, f-h.The amide 5e and the esters 8b, c, e reacted with β-maltose, thus affording the corresponding β-maltosyl esters 10b, c, e, whereas the compounds 8a-e reacted with β-glucose, yielding the corresponding β-glucosyl esters 11a-e.This appears to be one of the very few selective chemical modifications of sugars known, which do not involve the toilsome protection-deprotection methology.The now commercially available maltosyl and glucosyl esters 10e and 11d-e are new non-ionic, and water soluble detergents which could be used for studies of cell membrane proteins.

CHIMIE DES SUCRES SANS GROUPEMENTS PROTECTEURS: ESTERIFICATION REGIOSELECTIVE DE L'HYDROXYLE ANOMERE DU LACTOSE LIBRE

Treatment of α-lactose with acyl chlorides failed to give any pure products.However, the anomeric hydroxyl of lactose was esterified selectively and in high yields, by treating the free sugar with reactive acylating agents such as N-acyl thiazolidine-thiones or esters of p-nitrophenol, mercapto-benzothiazole and 8-hydroxy quinoline, making thus unnecessary the preliminary protection of the other hydroxyls of the lactose molecule.This appears to be one of the very few selective modifications of sugars known, which do not involve the classical protection-deprotection methodology.