Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H12O3 |
| Molecular Weight | 228.2433 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC=C(C=C1)C(=O)OCC2=CC=CC=C2
InChI
InChIKey=MOZDKDIOPSPTBH-UHFFFAOYSA-N
InChI=1S/C14H12O3/c15-13-8-6-12(7-9-13)14(16)17-10-11-4-2-1-3-5-11/h1-9,15H,10H2
| Molecular Formula | C14H12O3 |
| Molecular Weight | 228.2433 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Oestrogenic activity of benzylparaben. | 2003 Jan-Feb |
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| Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives. | 2004 Mar 12 |
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| A review of the endocrine activity of parabens and implications for potential risks to human health. | 2005 Jun |
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| Determination of parabens in pharmaceutical formulations by solid-phase microextraction-ion mobility spectrometry. | 2005 Sep 15 |
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| Optimisation of a solid-phase microextraction method for the determination of parabens in water samples at the low ng per litre level. | 2006 Aug 18 |
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| Parabens as urinary biomarkers of exposure in humans. | 2006 Dec |
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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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| Preliminary ecological risk assessment of butylparaben and benzylparaben -2. Fate and partitioning in aquatic environments. | 2007 |
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| Preliminary ecological risk assessment of butylparaben and benzylparaben -1. Removal efficiency in wastewater treatment, acute/chronic toxicity for aquatic organisms, and effects on medaka gene expression. | 2007 |
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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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| Inter-individual variability in esterases in human liver. | 2007 Sep 15 |
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| Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products. | 2008 |
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| Probabilistic ecological hazard assessment of parabens using Daphnia magna and Pimephales promelas. | 2009 Dec |
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| Parabens in male infertility-is there a mitochondrial connection? | 2009 Jan |
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| Evaluation of estrogenic activity of parabens and their chlorinated derivatives by using the yeast two-hybrid assay and the enzyme-linked immunosorbent assay. | 2009 Jan |
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| Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters. | 2009 Oct 16 |
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| Metabolism of parabens (4-hydroxybenzoic acid esters) by hepatic esterases and UDP-glucuronosyltransferases in man. | 2010 |
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| In-sample acetylation-non-porous membrane-assisted liquid-liquid extraction for the determination of parabens and triclosan in water samples. | 2010 Jul |
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| Self-reported chemicals exposure, beliefs about disease causation, and risk of breast cancer in the Cape Cod Breast Cancer and Environment Study: a case-control study. | 2010 Jul 20 |
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| Molecularly imprinted polymer for the extraction of parabens from environmental solid samples prior to their determination by high performance liquid chromatography-ultraviolet detection. | 2010 Mar 15 |
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| Urinary concentrations of four parabens in the U.S. population: NHANES 2005-2006. | 2010 May |
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| Occurrence and sources of selected phenolic endocrine disruptors in Ria de Aveiro, Portugal. | 2010 May |
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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 |
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| Removal of parabens from aqueous solution using β-cyclodextrin cross-linked polymer. | 2010 Sep 20 |
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| Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012 Nov 19 |
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| Effects of parabens on adipocyte differentiation. | 2013 Jan |
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| Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor α and β and androgen receptor. | 2013 Jul |
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| Inverse antagonist activities of parabens on human oestrogen-related receptor γ (ERRγ): in vitro and in silico studies. | 2013 Jul 1 |
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| The estrogenic effects of benzylparaben at low doses based on uterotrophic assay in immature SD rats. | 2013 Mar |
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| Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. | 2015 Feb |
Patents
Sample Use Guides
in mice (topical): of three daily doses of 33 mg to dorsal skin
in rats (intragastric): 0.16 mg/kg body up to 100 μg/kg body weight
Route of Administration:
Other
Benzylparaben was able to displace [(3)H]oestradiol from cytosolic oestrogen receptor (ER) of MCF7 human breast cancer cells by 22% at 1000-fold molar excess, by 40% at 10,000-fold molar excess, by 57% at 100 000-fold molar excess and by 100% at 1,000,000-fold molar excess. It was able to increase expression of a stably transfected oestrogen responsive reporter gene (ERE-CAT) in MCF7 cells after 24 h at 10(-5)M/10(-4)M and after 7 days at 10(-6)M/10(-5)M/10(-4)M. Proliferation of MCF7 cells could be increased by 10(-6)M/10(-5)M benzylparaben and this could be inhibited by 10(-7)M pure anti-oestrogen ICI 182,780, indicating that growth effects were ER mediated
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:51:28 GMT 2023
by
admin
on
Fri Dec 15 15:51:28 GMT 2023
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| Record UNII |
8Y41DYV4VG
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| Record Status |
Validated (UNII)
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| Record Version |
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NDF-RT |
N0000185508
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NCI_THESAURUS |
C92608
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C95327
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8080
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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SUB13025MIG
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SUB61024
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C057775
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202-311-9
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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BENZYLPARABEN
Created by
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PRIMARY | Description: A white to creamy white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; soluble in ethanol (~750 g/l) TS and ether R; dissolves in solutions of alkali hydroxides. Category: Antimicrobial preservative. Storage: Benzyl hydroxybenzoate should be kept in a well-closed container. Requirement: Benzyl hydroxybenzoate contains not less than 99.0% and not more than the equivalent of 101.0% of C14H12O3. | ||
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7180
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N0000175629
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PRIMARY | Increased Histamine Release [PE] | ||
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DTXSID9022526
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100000134265
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19075
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PRIMARY | RxNorm |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.52.pdf
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