U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H10O3
Molecular Weight 166.1739
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYLPARABEN

SMILES

CCOC(=O)C1=CC=C(O)C=C1

InChI

InChIKey=NUVBSKCKDOMJSU-UHFFFAOYSA-N
InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: http://www.fda.gov/Cosmetics/ProductsIngredients/Ingredients/ucm128042.htm http://www.connectchemicals.com/en/products-finder/ethyl-paraben-ep-120-47-8-153/?from=application-skin-care/function-preservative http://www.mattilsynet.no/kosmetikk/stoffer_i_kosmetikk/parabener/eus_vitenskapskomite_paa_kosmetikkomraadet_om_parabener_mars_2011.8143/binary/EUs%20vitenskapskomite%20på%20kosmetikkområdet%20om%20parabener%20mars%202011 http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_019.pdf

Ethylparaben is produced naturally and found in several fruits and insects, where it acts as an antimicrobial agent. Ethylparaben is mainly used as antiseptics in cosmetics, food and medicine (E number E214). It is also can be used as feed preservatives and antiseptic for bacteria. Ethylparaben is readily absorbed from the gastrointestinal tract or through the skin. It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body. Under the Federal Food, Drug, and Cosmetic Act (FD&C Act), cosmetic products and ingredients, other than color additives, do not need FDA approval before they go on the market. Broad concentration ranges reported in each product category in 1981 were < 0.1% and > 0.1% to 1%. Studies show the in vivo estrogenicity of MP and EP at human exposure levels, and indicate that populations exposed to large amounts of MP and EP may have a high burden of estrogenicity-related diseases.

CNS Activity

Curator's Comment: Known to be CNS penetrant in dog. Human data not available. After ethyl paraben is intravenously infused into the dog, unhydrolyzed ethyl paraben is found only in the brain.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Sequential injection chromatographic determination of ambroxol hydrochloride and doxycycline in pharmaceutical preparations.
2005 Dec 15
Fast simultaneous spectrophotometric determination of naphazoline nitrate and methylparaben by sequential injection chromatography.
2006 Sep 15
[Simultaneous determination of 7 kinds of preservatives and saccharin in foods with HPLC, and identification with LC/MS/MS].
2007 Dec
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products.
2008
The effect of McInnes solution on enamel and the effect of Tooth mousse on bleached enamel: An in vitro study.
2008 Apr
Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration.
2008 Dec
The effect of signal suppression and mobile phase composition on the simultaneous analysis of multiple classes of acidic/neutral pharmaceuticals and personal care products in surface water by solid-phase extraction and ultra performance liquid chromatography-negative electrospray tandem mass spectrometry.
2008 Feb 15
Skin protection creams in medical settings: successful or evil?
2008 Jul 25
Association of nicotinamide with parabens: effect on solubility, partition and transdermal permeation.
2008 Jun
Effect of pharmaceuticals on thermoreversible gelation of PEO-PPO-PEO copolymers.
2008 Jun 1
[Application of single drop microextraction in the determination of phthalate esters and parabens in drugs by gas chromatography-mass spectrometry].
2008 May
Do parabens have the ability to interfere with steroidogenesis?
2008 Nov
Ethyl-paraben and nicotinamide mixtures: apparent solubility, thermal behavior and X-ray structure of the 1:1 co-crystal.
2008 Nov
Influence of preservatives on the stability of ethyl glucuronide and ethyl sulphate in urine.
2008 Nov 20
Development and validation of a simple and rapid HPLC method for determination of pioglitazone in human plasma and its application to a pharmacokinetic study.
2008 Oct
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
A structural and thermal investigation of the inclusion of parabens in heptakis(2,6-di-O-methyl)cyclomaltoheptaose.
2008 Sep 22
Characterization and distribution of phenolics in carrot cell walls.
2008 Sep 24
Underarm antiperspirants/deodorants and breast cancer.
2009
Comparison of artificial sebum with human and hamster sebum samples.
2009 Feb 9
Parabens in male infertility-is there a mitochondrial connection?
2009 Jan
Analysis of parabens in cosmetics by low pressure liquid chromatography with monolithic column and chemiluminescent detection.
2009 Jul 15
4-Hydroxy-benzohydrazide.
2009 Jul 4
Combined online spectroscopic, calorimetric, and chemometric analysis: reaction enthalpy determinations in single and parallel reactions.
2009 Jun 2
Modeling the phase behavior in mixtures of pharmaceuticals with liquid or supercritical solvents.
2009 May 7
[Determination of six p-hydroxybenzoates in fruits and jams using solid-phase extraction-high performance liquid chromatography].
2009 Nov
Synthesis, characterization and texture observations of calamitic liquid crystalline compounds.
2009 Nov 4
Relating solubility data of parabens in liquid PEG 400 to the behaviour of PEG 4000-parabens solid dispersions.
2009 Oct
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009 Oct 16
Metabolism of parabens (4-hydroxybenzoic acid esters) by hepatic esterases and UDP-glucuronosyltransferases in man.
2010
Mixture effects of endocrine disrupting compounds in vitro.
2010 Apr
Hedge mustard (Sisymbrium officinale): chemical diversity of volatiles and their antimicrobial activity.
2010 Aug
[Chemical constituents of rhizoma imperatae and their anti-complementary activity].
2010 Dec
[Chemical constituents from aerial parts of Fallopia convolvulus].
2010 Dec
Ozonation of parabens in aqueous solution: kinetics and mechanism of degradation.
2010 Dec
Structure-toxicity relationship of phenolic analogs as anti-melanoma agents: an enzyme directed prodrug approach.
2010 Feb 12
Determination of parabens in cosmetic products using multi-walled carbon nanotubes as solid phase extraction sorbent and corona-charged aerosol detection system.
2010 Jan 1
A New Validated HPLC Method for the Simultaneous Determination of 2-phenoxyethanol, Methylparaben, Ethylparaben and Propylparaben in a Pharmaceutical Gel.
2010 Jul
Potential estrogenic effect(s) of parabens at the prepubertal stage of a postnatal female rat model.
2010 Jun
Use of a capillary tube for collecting an extraction solvent lighter than water after dispersive liquid-liquid microextraction and its application in the determination of parabens in different samples by gas chromatography--flame ionization detection.
2010 Jun 15
Urinary concentrations of four parabens in the U.S. population: NHANES 2005-2006.
2010 May
Occurrence and sources of selected phenolic endocrine disruptors in Ria de Aveiro, Portugal.
2010 May
Simultaneous quantitation of parabens, triclosan, and methyl triclosan in indoor house dust using solid phase extraction and gas chromatography-mass spectrometry.
2010 Oct 6
Regulation of the 5-HT3A receptor-mediated current by alkyl 4-hydroxybenzoates isolated from the seeds of Nelumbo nucifera.
2010 Sep
Removal of parabens from aqueous solution using β-cyclodextrin cross-linked polymer.
2010 Sep 20
Simultaneous determination of electroactive and non-electroactive food preservatives by novel capillary electrophoresis with amperometric detection.
2010 Sep 23
Effects of parabens on adipocyte differentiation.
2013 Jan
Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor α and β and androgen receptor.
2013 Jul
Inverse antagonist activities of parabens on human oestrogen-related receptor γ (ERRγ): in vitro and in silico studies.
2013 Jul 1
Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris.
2014 Jun
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ethyl paraben was mixed with the standard CE-2 powdered Wistar rats diet.
103 mg/kg/day for the 0.1% ethyl paraben
Route of Administration: Oral
The antimicrobial activities of ethylparaben on R. solanacearum, S. typhimurium, E. coli, F. oxysporum, A. niger, F. solani and F. moniliforme were investigated. In the test, the antibacterial activities were assayed using 20 U/mL streptomycin sulfate as a control. The antifungal activities were assayed using 100 mg/mL hygromycin as control. The 50 mg/mL crude antimicrobial extract dissolved with DMSO was poured into the wells and one well was used as a control. For antifungal activity, the plates were incubated at 28 °C for 2 days. For antibacterial activity, the plates were incubated at 30 °C for 24 h. Ethylparaben was found to inhibit these seven different types of microbes to different extents.
Name Type Language
ETHYLPARABEN
HSDB   II   INCI   MI   USP-RS  
INCI  
Official Name English
TEGOSEPT E
Common Name English
ETHYLPARABEN [USP-RS]
Common Name English
METHYL PARAHYDROXYBENZOATE IMPURITY B [EP IMPURITY]
Common Name English
E214
Code English
ETHYL P-HYDROXYBENZOATE
Common Name English
ETHYL HYDROXYBENZOATE
MART.   WHO-DD   WHO-IP  
Systematic Name English
ETHYLPARABEN [HSDB]
Common Name English
ASEPTOFORM E
Common Name English
ETHYL PARAHYDROXYBENZOATE [JAN]
Common Name English
ETHYL PARAHYDROXYBENZOATE E214
Common Name English
ETHYL P-OXYBENZOATE
Common Name English
ETHYL ESTER OF P-HYDROXYBENZOIC ACID
Common Name English
E-214
Code English
Ethyl 4-hydroxybenzoate
Systematic Name English
ETHYLPARABEN [II]
Common Name English
ETHYL HYDROXYBENZOATE [WHO-IP]
Common Name English
INS-214
Common Name English
ETHYL PARAHYDROXYBENZOATE [EP MONOGRAPH]
Common Name English
ETHYL HYDROXYBENZOATE [MART.]
Common Name English
ETHYLIS HYDROXYBENZOAS [WHO-IP LATIN]
Common Name English
ETHYL-P-HYDROXYBENZOATE
Common Name English
NSC-23514
Code English
Ethyl hydroxybenzoate [WHO-DD]
Common Name English
ETHYLPARABEN [INCI]
Common Name English
ETHYL PARAHYDROXYBENZOATE [EP IMPURITY]
Common Name English
ETHYL PARAHYDROXYBENZOATE
EP  
Systematic Name English
BENZOIC ACID, 4-HYDROXY-, ETHYL ESTER
Common Name English
INS NO.214
Common Name English
PROPYL HYDROXYBENZOATE IMPURITY C [EP IMPURITY]
Common Name English
ETHYLPARABEN [MI]
Common Name English
ETHYL PARABEN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C92608
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NDF-RT N0000185508
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CODEX ALIMENTARIUS (GSFA) INS-214
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WHO-VATC QD01AE10
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EPA PESTICIDE CODE 61202
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WHO-ATC D01AE10
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JECFA EVALUATION INS-214
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Code System Code Type Description
CHEBI
31575
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PRIMARY
FDA UNII
14255EXE39
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PRIMARY
ECHA (EC/EINECS)
204-399-4
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PRIMARY
NDF-RT
N0000184306
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PRIMARY Cell-mediated Immunity [PE]
HSDB
938
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PRIMARY
EVMPD
SUB11952MIG
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PRIMARY
ChEMBL
CHEMBL15841
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PRIMARY
NDF-RT
N0000175629
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PRIMARY Increased Histamine Release [PE]
DRUG BANK
DB13628
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PRIMARY
NCI_THESAURUS
C76710
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PRIMARY
MERCK INDEX
m5160
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PRIMARY Merck Index
EVMPD
SUB68647
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PRIMARY
PUBCHEM
8434
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PRIMARY
WIKIPEDIA
ETHYLPARABEN
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PRIMARY
EPA CompTox
DTXSID9022528
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PRIMARY
SMS_ID
100000092894
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PRIMARY
RS_ITEM_NUM
1267000
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PRIMARY
DAILYMED
14255EXE39
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PRIMARY
DRUG CENTRAL
4773
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PRIMARY
NSC
23514
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
ETHYLPARABEN
Created by admin on Fri Dec 15 15:13:29 GMT 2023 , Edited by admin on Fri Dec 15 15:13:29 GMT 2023
PRIMARY Chemical name. Ethyl p-hydroxybenzoate; ethyl 4-hydroxybenzoate.Other name: Ethylparaben.Description: Small colourless crystals or a white, crystalline powder; odourless or almost odourless.Solubility: Very slightly soluble in water; sparingly soluble in boiling water; freely soluble in ethanol (~750 g/l) TS and ether R.Category: Antimicrobial preservative.Storage: Ethyl hydroxybenzoate should be kept in a well-closed container.Additional information: Ethyl hydroxybenzoate is normally used in combination with other hydroxybenzoates.Requirement: Ethyl hydroxybenzoate contains not less than 99.0% and not more than the equivalent of 101.0% of C9H10O3 calculated with reference to the dried substance.
CAS
120-47-8
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PRIMARY
NDF-RT
N0000171131
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PRIMARY Allergens [Chemical/Ingredient]
RXCUI
1362892
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PRIMARY