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
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
| Molecular Formula | C9H10O3 |
| Molecular Weight | 166.1739 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Competitive binding of some alkyl p-hydroxybenzoates to human estrogen receptor alpha and beta]. | 2000 Dec |
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| Determination of ethyl-p-hydroxybenzoate in sow pancreatic juice by reversed-phase high-performance liquid chromatography. | 2001 Feb 25 |
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| Oestrogenic activity of parabens in MCF7 human breast cancer cells. | 2002 Jan |
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| In vivo and in vitro estrogen bioactivities of alkyl parabens. | 2003 Jul |
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| Diffusion of preservatives from topical dosage forms: a comparative study. | 2003 May-Jun |
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| [Quantitative determination of ethyl-p-hydroxybenzoate in resins extracted from Dracaena cochinchinensis with two technologies]. | 2004 Apr |
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| Estrogenic activity of cosmetic components in reporter cell lines: parabens, UV screens, and musks. | 2005 Feb 27 |
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| Preparation of C-6 substituted chitin derivatives under homogeneous conditions. | 2005 Jan-Feb |
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| Determination of parabens in pharmaceutical formulations by solid-phase microextraction-ion mobility spectrometry. | 2005 Sep 15 |
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| Expression profiling of estrogen-responsive genes in breast cancer cells treated with alkylphenols, chlorinated phenols, parabens, or bis- and benzoylphenols for evaluation of estrogenic activity. | 2006 May 25 |
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| The influence of physicochemical properties of preservative compounds on their distribution into various phases of oil in water submicron emulsion. | 2006 May-Jun |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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| Influence of crystal structure on the tableting properties of n-alkyl 4-hydroxybenzoate esters (parabens). | 2007 Dec |
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| Hydrolysis of a series of parabens by skin microsomes and cytosol from human and minipigs and in whole skin in short-term culture. | 2007 Dec 1 |
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| Simultaneous determination of antioxidants, preservatives and sweetener additives in food and cosmetics by flow injection analysis coupled to a monolithic column. | 2007 Jul 2 |
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| [Simultaneous determination of phthalates and parabens in cosmetic products by gas chromatography/mass spectrometry coupled with solid phase extraction]. | 2007 Mar |
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| Temporal stability of the conjugated species of bisphenol A, parabens, and other environmental phenols in human urine. | 2007 Sep |
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| The effect of McInnes solution on enamel and the effect of Tooth mousse on bleached enamel: An in vitro study. | 2008 Apr |
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| Do parabens have the ability to interfere with steroidogenesis? | 2008 Nov |
|
| Parabens in male infertility-is there a mitochondrial connection? | 2009 Jan |
|
| Mixture effects of endocrine disrupting compounds in vitro. | 2010 Apr |
|
| [Chemical constituents from aerial parts of Fallopia convolvulus]. | 2010 Dec |
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| Ozonation of parabens in aqueous solution: kinetics and mechanism of degradation. | 2010 Dec |
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| A New Validated HPLC Method for the Simultaneous Determination of 2-phenoxyethanol, Methylparaben, Ethylparaben and Propylparaben in a Pharmaceutical Gel. | 2010 Jul |
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| Potential estrogenic effect(s) of parabens at the prepubertal stage of a postnatal female rat model. | 2010 Jun |
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| Simultaneous quantitation of parabens, triclosan, and methyl triclosan in indoor house dust using solid phase extraction and gas chromatography-mass spectrometry. | 2010 Oct 6 |
|
| 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 |
|
| Identification of ethylparaben as the antimicrobial substance produced by Brevibacillus brevis FJAT-0809-GLX. | 2015 Mar |
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.
| Substance Class |
Chemical
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14255EXE39
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Validated (UNII)
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| Classification Tree | Code System | Code | ||
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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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31575
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14255EXE39
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204-399-4
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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938
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SUB11952MIG
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CHEMBL15841
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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DB13628
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C76710
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m5160
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SUB68647
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8434
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ETHYLPARABEN
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DTXSID9022528
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100000092894
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1267000
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14255EXE39
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4773
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23514
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ETHYLPARABEN
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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. | ||
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120-47-8
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N0000171131
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1362892
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SALT/SOLVATE -> PARENT | |||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
