1492-30-4

Usage

Uses

Used in Enzyme Activity Analysis:
4-Nitrophenyl palmitate is used as a substrate for lipase enzyme activity assays. The lipase enzyme hydrolyzes 4-nitrophenyl palmitate, yielding the yellow-colored product 4-nitrophenol, which can be measured spectrophotometrically at 410 nm. This application is valuable for researchers and scientists studying lipase activity, enzyme kinetics, and enzyme inhibition, as it allows for quick and accurate measurements of enzyme activity.
Used in Immobilization Methods:
In the field of biochemistry and biotechnology, 4-nitrophenyl palmitate is used as a substrate in the immobilization method of lipase on the interface of natural polysaccharide particles. This method is advantageous due to its short reaction time and the ease of performing spectrophotometric analyses, making it a preferred choice for studying enzyme immobilization and its effects on enzyme activity.
Used in Pharmaceutical Research:
4-Nitrophenyl palmitate is also utilized in pharmaceutical research as a tool to study the interactions between lipase enzymes and potential drug candidates. By understanding how these enzymes interact with various compounds, researchers can develop more effective drugs for treating lipase-related conditions and diseases.
Used in Analytical Chemistry:
In analytical chemistry, 4-Nitrophenyl palmitate is employed as a reference compound for the development and validation of new methods and techniques for enzyme activity analysis. Its well-defined properties and the ease of measuring its reaction product make it an ideal candidate for this purpose, allowing for the accurate assessment of new analytical methods and their effectiveness in measuring lipase activity.

InChI:InChI=1/C22H35NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(24)27-21-18-16-20(17-19-21)23(25)26/h16-19H,2-15H2,1H3

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 658-78-6 1-nitro-4-trifluoroacetoxy-benzene 
• 100-02-7 4-nitro-phenol 
• 112-67-4 n-hexadecanoyl chloride 

Downstream Products

• 906528-82-3 N-((2R,3R)-3-hydroxy-5-phenyl-1-(pyrrolidin-1-yl)pent-4-yn-2-yl)palmitamide 
• 628-97-7 hexadecanoic acid ethyl ester 
• 2239-78-3 propyl palmitate 
• 42232-25-7 hexyl hexadecanoate 
• 26718-83-2 heptyl palmitate 
• 112-39-0 hexadecanoic acid methyl ester 
• 13360-61-7 1-pentadecene 
• 100-02-7 4-nitro-phenol 
• 57-10-3 1-hexadecylcarboxylic acid 
• 86137-85-1 Hexadecanoic acid (2S,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl ester 
• 14609-74-6 p-nitrophenolate 
• 126624-40-6 (2R,4E)-2-N-hexadecanoylamino-4-octadecen-1-ol 
• 105243-34-3 (4E,8E,2S,3R)-N-hexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine 
• 116447-99-5 (2S,3R,4E)-1,3-benzylidene-2-(hexadecanoylamido)-4-octadecene-1,3-diol 

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.

Enzyme mediated-transesterification of verbascoside and evaluation of antifungal activity of synthesised compounds

Enzymatic acylation of verbascoside, a polyhydroxylated natural product, has been reported in this study using five different commercial lipases and taking p-nitrophenyl alkanoates as acyl donors. Out of these enzymes, the immobilised Candida antarctica lipase B was found as the enzyme of choice. Mono-and di-acylated products were formed, with mono as major product indicating high regioselective nature of such transformations. A series of acyl esters of verbascoside have been synthesised by this enzymatic transesterification methodology. The lipophilicity of the synthesised analogues was also checked. The analogues were further subjected to synergistic antifungal activity with amphotericin B (AmB) against Candida albicans. Fourfold reduction in minimum inhibitory concentration of AmB was observed with few synthesised analogues such as verbascoside 4″-octanoate (3b), verbascoside 4″-palmitate (3d) and verbascoside 4″,4′-dipalmitate (4d) at a concentration of 0.5 g/mL.

Fatty acid-binding site environments of serum vitamin D-binding protein and albumin are different

Vitamin D-binding protein (DBP) and albumin (ALB) are abundant serum proteins and both possess high-affinity binding for saturated and unsaturated fatty acids. However, certain differences exist. We surmised that in cases where serum albumin level is low, DBP presumably can act as a transporter of fatty acids. To explore this possibility we synthesized several alkylating derivatives of 14C-palmitic acid to probe the fatty acid-binding pockets of DBP and ALB. We observed that N-ethyl-5-phenylisooxazolium-3′-sulfonate-ester (WRK-ester) of 14C-palmitic acid specifically labeled DBP; but p-nitrophenyl- and N-hydroxysuccinimidyl-esters failed to do so. However, p-nitrophenyl ester of 14C-palmitic acid specifically labeled bovine ALB, indicating that the micro-environment of the fatty acid-binding domains of DBP and ALB may be different; and DBP may not replace ALB as a transporter of fatty acids.

Synthesis of Ceramide Analogues Having the C(4)-C(5) Bond of the Long-Chain Base as Part of an Aromatic or Heteroaromatic System

Two efficient and stereoselective methods are described for the preparation of aryl and heteroaryl ceramide analogues 2 and 3. The first route involves the addition of an aryllithium or a heteroaryllithium reagent (7a or 25a, respectively) to the L-serine-derived aldehyde 4, followed by hydrolysis of the oxazolidine, liberation of the amino group, and N-acylation. The second route, which was used to prepare arylceramide analogue 2 in eight steps and 28% overall yield starting with 3-bromobenzaldehyde, utilizes a Heck reaction to afford (E)-α,β-unsaturated ester 16, then osmium-catalyzed asymmetric dihydroxylation for the introduction of the desired chirality at C-2 and C-3. Regioselective α-azidation of α-O-nosyl-β-hydroxyester 18 with sodium azide, followed by LiAlH4 reduction of the azido and ester groups and N-acylation, complete the synthesis of arylceramide analogue 2.

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.

SYNTHESES OF D-ERYTHRO-1-DEOXYDIHYDROCERAMIDE-1-SULFONIC ACID AND PHOSPHONOSPHINGOGLYCOLIPID FOUND IN MARINE ORGANISM VIA A COMMON PRECURSOR

D-Erythro-1-deoxydihydroceramide-1-sulfonic acid, isolated from alkali-stable hydrogenated lipids in a non-photosynthetic marine diatom, Nitzschia alba, and (2S,3R)-N-palmitoyl-1-O--β-D-galactopyranosyl>-D-sphingosine, found in marine snail Turbo cornutus were synthesized via a common precursor (10) starting from galactose.

Synthesis and Biological Activity of the Isomers and Analogs of (4E,8E,2S,3R,2'R)-N-2'-Hydroxyhexadecanoyl-9-methyl-4,8-sphingadienine, the Ceramide Portion of the Fruiting-inducing Cerebroside in a Basidiomycete Schizophyllum commune

The title compounds were synthesized by employing 2-aminohexadecanoic acid and serine as the chiral sources, and served for an assay of fruiting-inducing activity on Schizophyllum commune.The structure-bioactivity relationship among closely related synthetic ceramides is discussed.

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.

the Effect of Hydrophobic-Lipophilic Interactions on Chemical Reactivity. 1. New Evidence for Intermolecular Aggregation and Self-Coiling

The hydrolytic behavior of 21 para-substituted phenyl esters of n-alkanoic acids (n-X) with various chain lengths in 60:40 (Φ=0.60), 50:50 (Φ=0.50), and 40:60 v/v (Φ=0.40) Me2SO-H2O mixtures was studied.Four new sets of experimental results which include departure from Hammett correlation for N-hexadecanoates (16-X), substantial differences in activation parameters, and effects of amylose on the kinetic parameters and on the activation parameters are presented along lines of reasoning mentioned by previous authors.These data establish that the aggregation and self-coiling of the n-alkanoate chain actually exist under experimental conditions.