1219-38-1

Basic information

• Product Name: Octyl paraben
• Synonyms: 4-hydroxy-benzoicacioctylester;octylp-hydroxybenzoate;p-hydroxybenzoicacidoctylester;p-hydroxy-benzoicacioctylester;4-HYDROXYBENZOIC ACID N-OCTYL ESTER;N-OCTYL 4-HYDROXYBENZOATE;N-OCTYL-P-HYDROXYBENZOATE;P-HYDROXYBENZOIC ACID N-OCTYL ESTER
• CAS NO: 1219-38-1
• Molecular Formula: C15H22O3
• Molecular Weight: 250.33
• EINECS: 214-943-2
• Product Categories: Aromatic Esters
• Mol File: 1219-38-1.mol

Chemical Properties

• Melting Point: 52-53°C
• Boiling Point: 172°C/0.1mmHg(lit.)
• Flash Point: 147.6 °C
• Appearance: /
• Density: 1.0589 (rough estimate)
• Vapor Pressure: 6.15E-06mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 8.23±0.15(Predicted)
• Water Solubility: Soluble in alcohol, phenoxy ethanol and propylene glycol. Insoluble in water.
• CAS DataBase Reference: Octyl paraben(CAS DataBase Reference)
• NIST Chemistry Reference: Octyl paraben(1219-38-1)
• EPA Substance Registry System: Octyl paraben(1219-38-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: DH2529050
• Hazardous Substances Data: 1219-38-1(Hazardous Substances Data)

Usage

Uses

N-Octyl 4-Hydroxybenzoate is a useful plasticizer.

InChI:InChI=1/C15H22O3/c1-2-3-4-5-6-7-12-18-15(17)13-8-10-14(16)11-9-13/h8-11,16H,2-7,12H2,1H3

Upstream product

• 111-87-5 octanol 
• 99-96-7 4-hydroxy-benzoic acid 
• 1486-51-7 p-(benzyloxy)benzoic acid 

Downstream Products

• 1194090-81-7 C₇₅H₇₈O₁₈ 
• 1298070-14-0 C₂₂H₂₆O₅ 
• 135329-85-0 C₃₁H₄₂O₆ 
• 135329-85-0 C₃₁H₄₂O₆ 
• 135329-89-4 C₂₃H₂₆O₅ 

Relevant articles and documents

Preparation method of benzoic acid high-carbon alcohol ester

The invention provides a preparation method of a benzoic acid higher alcohol ester. According to the preparation method, the benzoic acid higher alcohol ester is prepared by reaction of a benzoic acidcompound and a high carbon alcohol under the action of a sulfonic acid modified heterogeneous catalyst. The method has the beneficial effects that the production cost is low, the production process is safe, the post-treatment is simple, a large amount of industrial wastewater is avoided, and the method is more suitable for industrial production.

A microwave-assisted highly practical chemoselective esterification and amidation of carboxylic acids

The ubiquitousness of esters and amide functionalities makes their coupling reaction one of the most sought-after organic transformations. Herein, we have described an efficient microwave-assisted synthesis of esters and amides. Soluble triphenylphosphine, in conjugation with molecular iodine, gave the desired products without the requirement for a base/catalyst. In addition, a solid-phase synthetic route is incorporated for the said conversion, which has added advantages over solution-phase pathways, such as low moisture sensitivity, easy handling, isolation of the product by simple filtration, and reusability. In short, our method is simple, mild, green, and highly chemoselective in nature.

Gibbilimbol analogues as antiparasitic agents - Synthesis and biological activity against Trypanosoma cruzi and Leishmania (L.) infantum

The essential oils from leaves of Piper malacophyllum (Piperaceae) showed to be mainly composed by two alkenylphenol derivatives: gibbilimbols A and B. After isolation and structural characterization by NMR and MS data analysis, both compounds were evaluated against promastigote/amastigote forms of Leishmania (L.) infantum as well as trypomastigote/amastigote forms of Trypanosoma cruzi. The obtained results indicated that gibbilimbol B displayed potential against the tested parasites and low toxicity to mammalian cells, stimulating the preparation of several quite simple synthetic analogues in order to improve its activity and to explore the preliminary structure-activity relationships (SAR) data. Among the prepared derivatives, compound LINS03003 (n-octyl-4-hydroxybenzylamine) displayed the most potent IC50 values of 5.5 and 1.8 μM against amastigotes of T. cruzi and L. (L.) infantum, respectively, indicating higher activity than the natural prototype. In addition, this compound showed remarkable selectivity index (SI) towards the intracellular forms of Leishmania (SI = 13.1) and T. cruzi (SI = 4.3). Therefore, this work indicated that preparation of synthetic compounds structurally based in the bioactive natural products could be an interesting source of novel and selective compounds against these protozoan parasites.

Synthesis of Nipagin esters using acidic functional ionic liquids as catalysts

(Chemical Equation Presented) Several Bronsted acidic functional ionic liquids (FILs) with an alkane sulfonic acid group were synthesized. These FILs as dual solvent-catalysts for Nipagin esterification reactions were investigated. The results indicated that [HSO3-pMIM]HSO4 has the best catalytic activity and recyclability among the various kinds of FILs investigated, and its structure was characterized by infrared and NMR. The [HSO3-pMIM]HSO4 could be easily separated from the reaction mixture and reused without noticeably decreasing the catalytic activity. Copyright Taylor & Francis Group, LLC.

Discovery of a Small Molecule PDI Inhibitor That Inhibits Reduction of HIV-1 Envelope Glycoprotein gp120

Protein disulfide isomerase (PDI) is a promiscuous protein with multifunctional properties. PDI mediates proper protein folding by oxidation or isomerization and disrupts disulfide bonds by reduction. The entry of HIV-1 into cells is facilitated by the PDI-catalyzed reductive cleavage of disulfide bonds in gp120. PDI is regarded as a potential drug target because of its reduction activity. We screened a chemical library of natural products for PDI-specific inhibitors in a high-throughput fashion and identified the natural compound juniferdin as the most potent inhibitor of PDI. Derivatives of juniferdin were synthesized, with compound 13 showing inhibitory activities comparable to those of juniferdin but reduced cytotoxicity. Both juniferdin and compound 13 inhibited PDI reductase activity in a dose-dependent manner, with IC50 values of 156 and 167 nM, respectively. Our results also indicated that juniferdin and compound 13 exert their inhibitory activities specifically on PDI but do not significantly inhibit homologues of this protein family. Moreover, we found that both compounds can inhibit PDI-mediated reduction of HIV-1 envelope glycoprotein gp120.

Dipole architecture of molecules and mesomorphic behavior of liquid crystals with rigid T-shaped mesogenic fragment

A number of liquid crystalline polyesters having a rigid T-shaped mesogenic fragment and differing in dipole architecture were synthesized and examined by polarizing optical microscopy, differential scanning calorimetry, and IR and 1H NMR spectroscopy. The thermal stability of the mesophase in the given series of compounds was shown to increase with extension of arms in the T-shaped mesogenic fragment, as well as on replacement of the terminal ester groups (COOAlk) therein by ether moieties (OAlk). Such replacement also enhances smectogenic properties.

Inhibition of estrone sulfatase (ES) by alkyl and cycloalkyl ester derivatives of 4-[(aminosulfonyl)oxy] benzoic acid

In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess potent inhibitory activity, indeed the cyclooctyl derivative was found to be more potent than 667-COUMATE, which is currently undergoing clinical trials.

Lipoxygenase Inhibitory Activity of Octyl Gallate

Octyl gallate inhibited soybean lipoxygenase-1 (EC 1.13.11-12, type I) with an IC50 of 1.3 μM. The inhibition of the enzyme by octyl gallate is a slow and reversible reaction without residual activity. The inhibition kinetics analyzed by Lineweaver-Burk plots indicates that octyl gallate is a competitive inhibitor, and the inhibition constant, KI, was obtained as 0.54 μM. One molecule of octyl gallate scavenged six molecules of 1,1-diphenyl-2-picrylhydrazyl and inhibited autoxidative lipid peroxidation. In addition, octyl gallate was effective in preventing lipid peroxidation.

Synthesis and biochemical evaluation of some novel benzoic acid based esters as potential inhibitors of oestrone sulphatase

Oestrone sulphatase is an important target in the fight against hormone-dependent breast cancer. In an effort to investigate the reported definitive pharmacophore for oestrone sulphatase and continue our search for potent inhibitors of this enzyme, we have undertaken extensive synthesis, biochemical evaluation and physicochemical property determination of a range of benzoic acid based esters. Here, we report the initial results of our study into a series of straight chain alkyl esters of 4-sulphonylbenzoic acid. Using these compounds, we have investigated the involvement of two physicochemical properties, namely logP and pKa. The results of this study show that there was a strong correlation between the inhibitory activity and the logP of the parent compound. Within the series of compounds studied, hydrophobicity appears to be a more important factor than pKa in determining the overall inhibitory activity. In a previous report, we showed that pKa plays an important role in stabilizing the phenoxide ion resulting from the hydrolysis of the sulphamate group. Here, we propose that although pKa is an important factor in determining the overall inhibitory activity when a wide range of compounds are considered, both hydrophobicity and pKa need to be considered in the design of potential inhibitors of oestrone sulphatase.

Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid

In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of straight chain alkyl esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess greater inhibitory activity when compared to COUMATE, although they were all found to possess lower inhibitory activity with respect to EMATE. Furthermore, the data suggest a strong correlation between logP and IC50 and therefore adds further support to our previous report where we suggested a link between inhibitory activity and hydrophobicity.