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Details

Stereochemistry ACHIRAL
Molecular Formula C14H11O3.Na
Molecular Weight 250.2251
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYLPARABEN SODIUM

SMILES

[Na+].[O-]C1=CC=C(C=C1)C(=O)OCC2=CC=CC=C2

InChI

InChIKey=JSMLEGBBJQVZGJ-UHFFFAOYSA-M
InChI=1S/C14H12O3.Na/c15-13-8-6-12(7-9-13)14(16)17-10-11-4-2-1-3-5-11;/h1-9,15H,10H2;/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C14H11O3
Molecular Weight 227.2353
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Benzylparaben (BzP), a type of parabens being used as a preservative agent in cosmetics, food, and pharmaceutical products. It is an allergic compound, which was shown to fit well into the agonist pocket of human estrogen receptor α (hERα).

Approval Year

1994
152
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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.
2015-02
Inverse antagonist activities of parabens on human oestrogen-related receptor γ (ERRγ): in vitro and in silico studies.
2013-07-01
Comparative study on transcriptional activity of 17 parabens mediated by estrogen receptor α and β and androgen receptor.
2013-07
The estrogenic effects of benzylparaben at low doses based on uterotrophic assay in immature SD rats.
2013-03
Effects of parabens on adipocyte differentiation.
2013-01
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.
2012-11-19
Simultaneous quantitation of parabens, triclosan, and methyl triclosan in indoor house dust using solid phase extraction and gas chromatography-mass spectrometry.
2010-10-06
Removal of parabens from aqueous solution using β-cyclodextrin cross-linked polymer.
2010-09-20
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.
2010-07-20
In-sample acetylation-non-porous membrane-assisted liquid-liquid extraction for the determination of parabens and triclosan in water samples.
2010-07
Urinary concentrations of four parabens in the U.S. population: NHANES 2005-2006.
2010-05
Occurrence and sources of selected phenolic endocrine disruptors in Ria de Aveiro, Portugal.
2010-05
Molecularly imprinted polymer for the extraction of parabens from environmental solid samples prior to their determination by high performance liquid chromatography-ultraviolet detection.
2010-03-15
Metabolism of parabens (4-hydroxybenzoic acid esters) by hepatic esterases and UDP-glucuronosyltransferases in man.
2010
Probabilistic ecological hazard assessment of parabens using Daphnia magna and Pimephales promelas.
2009-12
Ultra-high-performance liquid chromatography-tandem mass spectrometry for determining the presence of eleven personal care products in surface and wastewaters.
2009-10-16
Parabens in male infertility-is there a mitochondrial connection?
2009-01
Evaluation of estrogenic activity of parabens and their chlorinated derivatives by using the yeast two-hybrid assay and the enzyme-linked immunosorbent assay.
2009-01
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products.
2008
Hydrolysis of a series of parabens by skin microsomes and cytosol from human and minipigs and in whole skin in short-term culture.
2007-12-01
Inter-individual variability in esterases in human liver.
2007-09-15
Preliminary ecological risk assessment of butylparaben and benzylparaben -2. Fate and partitioning in aquatic environments.
2007
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
Parabens as urinary biomarkers of exposure in humans.
2006-12
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Optimisation of a solid-phase microextraction method for the determination of parabens in water samples at the low ng per litre level.
2006-08-18
Determination of parabens in pharmaceutical formulations by solid-phase microextraction-ion mobility spectrometry.
2005-09-15
A review of the endocrine activity of parabens and implications for potential risks to human health.
2005-06
Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives.
2004-03-12
Oestrogenic activity of benzylparaben.
2003-01-09
Patents

Patents

05231113
5
05919970
9
06982348
10

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Mon Mar 31 21:27:53 GMT 2025
Edited
by admin
on Mon Mar 31 21:27:53 GMT 2025
Record UNII
82W7I990AN
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZYLPARABEN SODIUM
Common Name English
BENZOIC ACID, 4-HYDROXY-, PHENYLMETHYL ESTER, SODIUM SALT
Preferred Name English
BENZOIC ACID, 4-HYDROXY-, PHENYLMETHYL ESTER, SODIUM SALT (1:1)
Common Name English
BENZOIC ACID, P-HYDROXY-, BENZYL ESTER, SODIUM SALT
Common Name English
SODIUM BENZYL PARAHYDROXYBENZOATE
Systematic Name English
SODIUM BENZYL 4-HYDROXYBENZOATE
Systematic Name English
BENZYL P-HYDROXYBENZOATE SODIUM SALT
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002753
Created by admin on Mon Mar 31 21:27:53 GMT 2025 , Edited by admin on Mon Mar 31 21:27:53 GMT 2025
PRIMARY
CAS
5693-29-8
Created by admin on Mon Mar 31 21:27:53 GMT 2025 , Edited by admin on Mon Mar 31 21:27:53 GMT 2025
PRIMARY
PUBCHEM
71586812
Created by admin on Mon Mar 31 21:27:53 GMT 2025 , Edited by admin on Mon Mar 31 21:27:53 GMT 2025
PRIMARY
FDA UNII
82W7I990AN
Created by admin on Mon Mar 31 21:27:53 GMT 2025 , Edited by admin on Mon Mar 31 21:27:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID40205476
Created by admin on Mon Mar 31 21:27:53 GMT 2025 , Edited by admin on Mon Mar 31 21:27:53 GMT 2025
PRIMARY
Related Record Type Details
Structure of BENZYLPARABEN
PARENT -> SALT/SOLVATE
NIH
NCATS
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