4-Hydroxybenzoic Acid Ethyl Ester - CAS 120-47-8
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
4-Hydroxybenzoic Acid Ethyl Ester
Catalog Number:
120-47-8
Synonyms:
Ethyl 4-hydroxybenzoate
CAS Number:
120-47-8
Description:
4-Hydroxybenzoic Acid Ethyl Ester could be commonly used in cosmetic products as an antimicrobial agent.
Molecular Weight:
166.17
Molecular Formula:
C9H10O3
Quantity:
Grams-Kilos
Quality Standard:
Enterprise Standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CCOC(=O)C1=CC=C(C=C1)O
InChI:
InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
InChIKey:
NUVBSKCKDOMJSU-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 120-47-8 4-Hydroxybenzoic Acid Ethyl Ester

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Reference Reading


1.Novel olefinic-centered macroacyclic compounds involving tetrasubstituted 4-hydroxybenzoic acid fragments: synthesis, structural characterization and comparison of experimental and computational results.
Er M1, Değirmencioğlu İ2, Tahtacı H3. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 15;139:68-74. doi: 10.1016/j.saa.2014.12.030. Epub 2014 Dec 18.
Dialkyl 4,4'-(2-(1,3-bis(4-(alkoxycarbonyl)phenoxy)propan-2-ylidene)propane-1,3-diyl)bis (oxy)dibenzoate 6a,b were synthesized through the reaction of ethene-1,1,2,2,-tetra-yl-tetra methylene tetra bromide 1 with methyl 4-hydroxy benzoate or ethyl 4-hydroxy benzoate 2a,b. In addition, compounds 6a,b were obtained by using the esterification reaction from the reaction compound 5 with methyl and ethyl alcohol in high yields. Compound 4 was synthesized from the reaction of ethene-1,1,2,2,-tetra-yl-tetra methylene tetra bromide 1 with 4-hydroxy benzonitrile 3. The structures of the novel synthesized compounds were confirmed by IR, (1)H NMR, (13)C NMR, COSY, elemental analysis, and mass spectral data. Compound 6b, C42H44O12, was also characterized with additional analysis such as UV-vis, and X-ray spectral techniques. The electronic structure of compound 6b was studied by DFT level 6-31G∗(d,p) using X-ray crystallographic data. The results obtained from this study are consistent with the X-ray data.
2.Metabolism of parabens (4-hydroxybenzoic acid esters) by hepatic esterases and UDP-glucuronosyltransferases in man.
Abbas S1, Greige-Gerges H, Karam N, Piet MH, Netter P, Magdalou J. Drug Metab Pharmacokinet. 2010;25(6):568-77. Epub 2010 Oct 1.
Parabens (alkyl esters of 4-hydroxybenzoic acid) are widely used as preservatives in drugs, cosmetic products, and foodstuffs. Safety concerns have recently increased due to the potential health risks associated to exposure to large amounts of these substances. Biotransformation of parabens mainly includes hydrolysis of the ester bond and glucuronidation reactions. The hydrolysis and glucuronidation of a series of six parabens differing by the nature of the alkyl group were investigated in human liver microsomes and plasma, and the major human UDP-glucuronosyltransferase (UGT) isoforms involved in the reaction were identified. Methyl- and ethylparaben were stable in human plasma, with 95% of the initial concentration remaining after 24 h. On the other hand, propyl-, butyl- and benzylparaben concentrations decreased by 50% under similar conditions. In contrast, rapid hydrolysis was measured with human liver microsomes depending on the alkyl chain length, with t(1/2) varying from 22 min for methylparaben to 87 min for butylparaben.
3.A novel Aspergillus oryzae esterase that hydrolyzes 4-hydroxybenzoic acid esters.
Koseki T1, Mihara K, Murayama T, Shiono Y. FEBS Lett. 2010 Sep 24;584(18):4032-6. doi: 10.1016/j.febslet.2010.08.021. Epub 2010 Aug 20.
In this study we report the biochemical characterization of a hypothetical protein from Aspergillus oryzae exhibiting sequence identity with feruloyl esterase and tannase from the genus Aspergillus. The purified recombinant protein showed a hydrolytic activity toward the ethyl, propyl, or butyl esters of 4-hydroxybenzoic acid, but did not show feruloyl esterase or tannase activity. Finally, the enzyme decreased the antimicrobial activity of parabens against A. oryzae via hydrolysis of the ester bond present in butyl 4-hydroxybenzoic acid.
4.Preparation and evaluation of molecularly imprinted microspheres for solid-phase extraction of 1,4-hydroxybenzoic acid esters in soy.
He J1, Shen Y, Chen S, Wei H, Zhu J, You L, Lu K. J Sep Sci. 2011 Oct;34(19):2739-44. doi: 10.1002/jssc.201100452. Epub 2011 Aug 24.
Molecularly imprinted microspheres (MIMs) were prepared by precipitation polymerization for the binding and recognition of 1,4-hydroxybenzoic acid esters. Ethyl p-hydroxybenzoate (EtPHB) was used as the template molecule, methacrylic acid as the functional monomer, ethylene dimethacrylate as the linking agent. It was evaluated by solid-phase extraction column packed with MIMs combined with liquid chromatography to determine trace preservatives including benzoic acid, methyl p-hydroxybenzoate, EtPHB, propyl p-hydroxybenzoate in food products. A solid-phase extraction based on MIM procedure was used to isolate four additives from the food matrix before quantitative analysis. The Scatchard plot suggested that the template-polymer system had two-site binding behavior with the dissociation constants of 0.3577 and 3.952 mg/g, respectively. The rebinding test, based on the molecularly imprinted solid-phase extraction column technique, showed the recoveries of soy samples spiked with four additives within 88.