1956-10-1

Usage

Uses

Used in Biochemical Research:
4-Nitrophenyl caprylate is used as a substrate for measuring the activity of esterases and lipases in biological samples. It aids in understanding the kinetics and mechanisms of these enzymes, which is crucial for the study of their functions and potential applications in medicine and biotechnology.
Used in Enzyme Assays:
4-Nitrophenyl caprylate is used as a colorimetric indicator in enzyme assays. The release of the 4-nitrophenol group upon enzymatic hydrolysis results in a color change, allowing for the quantification of enzyme activity. This is particularly useful in the development and optimization of new enzymes or in the assessment of enzyme inhibitors.
Used in Pharmaceutical Development:
4-Nitrophenyl caprylate is used as a starting material or intermediate in the synthesis of pharmaceutical compounds. Its reactivity and solubility properties make it a valuable component in the development of new drugs, particularly those targeting esterases and lipases.
Used in Organic Chemistry:
4-Nitrophenyl caprylate is used as a reagent in various organic synthesis processes. Its unique structure allows for the formation of new compounds with potential applications in different industries, such as the production of specialty chemicals, agrochemicals, and materials science.
Used in Educational Purposes:
4-Nitrophenyl caprylate is used as a teaching aid in laboratory courses and demonstrations. It provides students with hands-on experience in conducting enzyme assays and understanding the principles of enzyme kinetics, which is essential for their education in biochemistry and related fields.

InChI:InChI=1/C14H19NO4/c1-2-3-4-5-6-7-14(16)19-13-10-8-12(9-11-13)15(17)18/h8-11H,2-7H2,1H3

Upstream product

• 124-07-2 Octanoic acid 
• 7693-46-1 4-Nitrophenyl chloroformate 
• 956-75-2 p-nitrophenyl hexanoate 
• 143-07-7 lauric acid 
• 100-02-7 4-nitro-phenol 
• 1956-11-2 p-Nitrophenyl laurate 
• 2450-13-7 Heptyl-thiooctanoat 
• 111-64-8 n-octanoic acid chloride 

Downstream Products

• 74713-59-0 N-octanoylsphingosine 
• 100-02-7 4-nitro-phenol 
• 59051-71-7 Octanoylsulfanyl-acetic acid 
• 24928-30-1 N-butyloctanamide 
• 14609-74-6 p-nitrophenolate 
• 124-07-2 Octanoic acid 
• 1332570-02-1 N-((2S,3R,E)-5-(4-(tert-butyl)phenyl)-1,3-dihydroxypent-4-en-2-yl)octanamide 
• 1332570-04-3 N-((2S,3R,E)-5-(4-heptylphenyl)-1,3-dihydroxypent-4-en-2-yl)octanamide 
• 1332570-01-0 N-((2S,3R,E)-1,3-dihydroxy-5-(4-methoxyphenyl)pent-4-en-2-yl)octanamide 
• 1984-06-1 sodium caprylate 
• 83626-91-9 Octanoic acid 4-[bis-(2-chloro-ethyl)-amino]-phenyl ester 
• 83645-54-9 Octanoic acid 4-[bis-(2-hydroxy-ethyl)-amino]-phenyl ester 
• 158983-55-2 N-Octanoyl-1-O-benzoyl-3-O-tetrahydropyranyl-D-erythro-sphingosine 
• 158983-54-1 N-Octanoyl-1-O-benzoyl-D-erythro-sphingosine 

Relevant academic research and scientific papers

A REMARKABLE ENHANCEMENT OF THE RATE OF ESTER THIOLYSIS BY SYNTHETIC AMPHIPHILE VESICLES

Cationic surfactant vesicles accelerate the rate of thiolysis of p-nitrophenyl octanoate by n-heptyl-mercaptan by several million fold in the pH range from 4 to 6, providing an efficient system for ester thiolysis in aqueous solution that is functional even at pH4, i.e. more than 6 pH units below the pKa of the SH group.Analysis of the data in terms of an ion exchange formalism implies that this rate acceleration is due primarily to concentration of the reagents in the dimensionally-restricted environment provided by the vesicle, coupled with small contributions from enhanced dissociation and reactivity of the nucleophile at the vesicle surface(s).

One for Many: A Universal Reagent for Acylation Processes

This work describes acylation reactions facilitated by a type of heterocycle-based acyl transfer agent, 2-acyloxypyridazinone. Reactions of 2-acyloxypyridazinone with carboxylic acids yield mixed carbonic anhydride intermediates, which are reactive and could be coupled with a wide range of substrates including acids, amines, alcohols, and thiols. The wide substrate scope, ease of operation (no additive or catalyst), storage and handling stability, and atom-efficiency from recycling the heterocycle carrier make the reported acylating agent attractive for acylation-based coupling reactions.

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.

Hydrolysis of hydrophobic esters in a bicontinuous microemulsion catalysed by lipase B from Candida antarctica

Selective enzyme-catalysed biotransformations offer great potential in organic chemistry. However, special requirements are needed to achieve optimum enzyme activity and stability. A bicontinuous microemulsion is proposed as reaction medium because of its

Ytterbium triflate catalysed Friedel-Crafts reaction using carboxylic acids as acylating reagents under solvent-free conditions

The Friedel-Crafts acylation of 1-naphthol and phenol derivatives with carboxylic acids were investigated by using a catalytic amount of metal-triflate, in particular Yb(OTf)3, under solvent-free conditions. Both aliphatic and aromatic carboxylic acids reacted easily to afford the corresponding hydroxyaryl ketones.

Stable gene variants of lipases

The present invention relates to the generation and production of novel thermostable, organic solvent stable and pH tolerant lipase gene variants. The invention also relates to methods of selecting lipase variants for high temperatures and for their purification.

Inhibition of the Hydrolysis of p-Nitrophenyl Esters by Association with an Erythromycin A Derivative

The alkaline hydrolysis of p-nitrophenyl esters (1) of an homologous series of straight chain acids and derivatives of naphthoic acids was studied in the presence of the antibiotic erythromycin A (E) and its hydrolysis product (Z).While (E) does not affect the hydrolysis of 1, (Z) inhibits this reaction.The observed pseudo-first-order rate constants decrease as the Z concentration increases and they tend to a minimum value.This inhibition is ascribed to the formation of a host-guest complex between Z and 1.It is suggested that the attack of an external HO- at the carbonyl ester group is hindered by steric and electrostatic effects.The association constants and the second-order rate constants for the complexed esters were calculated.The inhibition tends to be complete for esters of alkyl chains with an add number of carbon atoms.Such a trend is probably related to the geometric requirements of inclusion.

A Simple and Mild Esterification Method for Carboxylic Acids Using Mixed Carboxylic-Carbonic Anhydrides

A simple and mild esterification method using mixed carboxylic-carbonic anhydrides has been developed.Simple aliphatic carboxylic esters are prepared in high yields by the reaction of acids with equimolar amounts of chloroformates (2,2,2-trichloroethyl chloroformate is an exception) and triethylamine in the presence of a catalytic amount of 4-(dimethylamino)pyridine.Although aromatic acids give a mixture of the ester, the acid anhydride, and the carbonate under normal conditions utilized in this study, it is found that increasing the amount of 4-(dimethylamino)pyridine drastically decreases the formation of the acid anhydride and the carbonate, affording a satisfactory yield of the ester.This method reaches a limit with sterically hindered acids and the formation of the acid anhydride and the carbonate is favored.