BUTYLPARABEN

First approved in 1984

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H14O3
Molecular Weight	194.2271
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCOC(=O)C1=CC=C(O)C=C1

InChI

InChIKey=QFOHBWFCKVYLES-UHFFFAOYSA-N

InChI=1S/C11H14O3/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7,12H,2-3,8H2,1H3

HIDE SMILES / InChI

Molecular Formula	C11H14O3
Molecular Weight	194.2271
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28208728 | https://www.ncbi.nlm.nih.gov/pubmed/28318231

Parabens are widely used preservatives in basic necessities such as cosmetic and pharmaceutical products. It was found, that butylparaben has estrogenic and antiandrogenic properties and is known to reduce sperm counts in rats following perinatal exposure. In addition was observed, that butylparaben exerted endocrine disrupting effects on both male and female offspring. In 2009-2010, 80 pregnant women from Ottawa Canada participated in the Plastics and Personal-Care Product Use in Pregnancy (P4) Study. Women kept a diary of products that they used 24 h prior to and during the collection. All parabens measured in maternal urine had moderate to high reproducibility. Women who used lotions in the past 24 h had significantly higher geometric mean paraben concentrations (80-110%) in their urine than women who reported no use in the past 24 h. Women who used shampoo, conditioner, and cosmetics also showed 70-80% higher butylparaben concentrations in their urine.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.drugs.com/imprints/barr-10-mg-876-1410.html	Inactive ingredient		Approved 8583	Fluoxetine Approved Use luoxetine is indicated for the treatment of Major Depressive Disorder (MDD). The efficacy of Fluoxetine in MDD was established in one 5-week trial, three 6-week trials, and one maintenance study in adults. The efficacy of Fluoxetine was also established in two 8- to 9-week trials in pediatric patients 8 to 18 years of age Launch Date 1987
Unknown 2596

F_unbound

Value	Dose	Co-administered	Analyte	Population
3.71% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33188879/			BUTYLPARABEN plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
rCYP1A2 5 SULT 6 rCYP3A 6 CYP19A1 429 BCRP 910 rCYP2B 4 rCYP2C 4 rCYP1A1 4 P-gp 1741 CYP2C19 2057 rCYP2E1 4 UMAT 30 CYP1A2 2153	UGT1A1 479 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A3 470 UGT1A4 399 UGT1A10 331 UGT2B7 456 UGT2B15 236 SULT1A1 37 UGT2B17 237 SULT2A1 28 SULT1E1 22 UGT2B4 278 CES1 45

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/891#sid=11112246	inconclusive [IC50 12.5893 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1645841#sid=170465688	inconclusive [IC50 17.3768 uM]
rCYP2E1 6	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	likely [IC50 260 uM]
rCYP3A 10	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	likely [IC50 32.3 uM]
rCYP1A2 6	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	likely [IC50 43.3 uM]
rCYP1A1 5	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	likely [IC50 59.8 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1325#sid=22405509	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/743083#sid=144210650	no
P-gp 1932	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/799#sid=22405509	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1326#sid=22405509	no
UMAT 30	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/602162#sid=22405509	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/410#sid=11112246 \| https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170465688	yes [IC50 0.0794 uM]
rCYP2B 9	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 12 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671198#sid=170465688	yes [IC50 13.3768 uM]
rCYP2C 4	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27432241/	yes [IC50 14.8 uM]
SULT 6	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17306434/	yes [IC50 37 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1671199#sid=170465688	yes [IC50 6.3096 uM]
rGST 3	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/32623865/	yes

Drug as victim

Target	Modality	Activity
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	likely
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	likely
SULT1A1 37	substrate 4014 Sources: https://www.efsa.europa.eu/en/efsajournal/pub/3978	major
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	weak
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	weak
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	weak
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	weak
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes [Km 190 uM]
CES1 45	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes
SULT1E1 22	substrate 4014 Sources: https://www.efsa.europa.eu/en/efsajournal/pub/3978	yes
SULT2A1 28	substrate 4014 Sources: https://www.efsa.europa.eu/en/efsajournal/pub/3978	yes
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/20930423/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/588834#sid=17390002

PubMed

Title	Date	PubMed
Effects of butylparaben on the male reproductive system in rats.	2001 Feb	12004923
Controlled drug release from gels using surfactant aggregates: I. Effect of lipophilic interactions for a series of uncharged substances.	2001 Sep	11745775
Effects of propyl paraben on the male reproductive system.	2002 Dec	12419695
The effect of surface charge and partition coefficient on the chemical stability of solutes in O/W emulsions.	2002 Feb	11835213
Oestrogenic activity of parabens in MCF7 human breast cancer cells.	2002 Jan	11867263
Effects of butyl paraben on the male reproductive system in mice.	2002 Jul	12111007
Oestrogenic activity of isobutylparaben in vitro and in vivo.	2002 Jul-Aug	12210538
Additive estrogenic activities of the binary mixtures of four estrogenic chemicals in recombinant yeast expressing human estrogen receptor.	2002 Mar	14614265
Decreased sperm number and motile activity on the F1 offspring maternally exposed to butyl p-hydroxybenzoic acid (butyl paraben).	2002 Mar	11999442
[Analysis of preservatives in cosmetics by gas chromatography].	2002 May	12541956
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.	2002 Nov 15	12198127
Determination of cisapride, its oxidation product, propyl and butyl parabens in pharmaceutical dosage form by reversed-phase liquid chromatography.	2003 Dec 4	14656590
Oestrogenic activity of benzylparaben.	2003 Jan-Feb	12518336
In vivo and in vitro estrogen bioactivities of alkyl parabens.	2003 Jul	15697177
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004 Apr	15272608
Developmental toxicity evaluation of butylparaben in Sprague-Dawley rats.	2004 Aug	15334527
Separation of preservatives in cosmetic products by micellar electrokinetic chromatography.	2004 Dec	15636528
Effect of heat on the percutaneous absorption and skin retention of three model penetrants.	2004 Feb	14757507
Biotransformation of chlorpropham (CIPC) in isolated rat hepatocytes and xenoestrogenic activity of CIPC and its metabolites by in vitro assays.	2004 Mar	15204698
Morphometric analysis of mice uteri treated with the preservatives methyl, ethyl, propyl, and butylparaben.	2004 Sep	15941009
Comment on developmental toxicity evaluation of butylparaben in Sprague-Dawley rats.	2005 Feb	15729729
Safety assessment of esters of p-hydroxybenzoic acid (parabens).	2005 Jul	15833376
Decrease in skin permeation and antibacterial effect of parabens by a polymeric additive, poly(2-methacryloyloxyethyl phosphorylcholine-co-butylmetacrylate).	2005 Mar	15744096
Estrogenicity of butylparaben in rainbow trout Oncorhynchus mykiss exposed via food and water.	2005 May 15	15848249
The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants.	2005 Sep 14	16019171
Practical constraints in the kinetic plot representation of chromatographic performance data: theory and application to experimental data.	2006 Apr 1	16579593
Simultaneous analysis of antioxidants and preservatives in cosmetics by supercritical fluid extraction combined with liquid chromatography-mass spectrometry.	2006 Jul 7	16513127
Acceleration of paraben sorption to polyethylene terephthalate: a freeze-thaw phenomenon.	2006 Jul-Aug	17089692
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	16280211
The influence of physicochemical properties of preservative compounds on their distribution into various phases of oil in water submicron emulsion.	2006 May-Jun	17089686
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Flow cytometric cell cycle analysis allows for rapid screening of estrogenicity in MCF-7 breast cancer cells.	2006 Oct	16797915
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	18382416
Variability in human skin permeability in vitro: comparing penetrants with different physicochemical properties.	2007 Apr	17177207
Systemic uptake of diethyl phthalate, dibutyl phthalate, and butyl paraben following whole-body topical application and reproductive and thyroid hormone levels in humans.	2007 Aug 1	17822133
[Simultaneous determination of 7 kinds of preservatives and saccharin in foods with HPLC, and identification with LC/MS/MS].	2007 Dec	18203501
Influence of crystal structure on the tableting properties of n-alkyl 4-hydroxybenzoate esters (parabens).	2007 Dec	17542021
Simultaneous determination of seven phthalates and four parabens in cosmetic products using HPLC-DAD and GC-MS methods.	2007 Jan	17313141
Comparison of the global gene expression profiles produced by methylparaben, n-butylparaben and 17beta-oestradiol in MCF7 human breast cancer cells.	2007 Jan-Feb	17121429
Simultaneous determination of antioxidants, preservatives and sweetener additives in food and cosmetics by flow injection analysis coupled to a monolithic column.	2007 Jul 2	17586119
[Simultaneous determination of nine kinds of preservatives in foods by HPLC].	2007 Jun	17657998
[Enhancement of di-n-butyl phthalate on the estrogenic activities of esters of p-hydroxybenzoic acid].	2007 May	17712932
Temporal stability of the conjugated species of bisphenol A, parabens, and other environmental phenols in human urine.	2007 Sep	17410114
Lack of effect of butylparaben and methylparaben on the reproductive system in male rats.	2008 Apr	18393383
Analysis and quantification of parabens in cosmetic products by utilizing hollow fibre-supported liquid membrane and high performance liquid chromatography with ultraviolet detection.	2008 Aug	18713076
[Application of single drop microextraction in the determination of phthalate esters and parabens in drugs by gas chromatography-mass spectrometry].	2008 May	18724664
Do parabens have the ability to interfere with steroidogenesis?	2008 Nov	18648085
The membrane lateral pressure-perturbing capacity of parabens and their effects on the mechanosensitive channel directly correlate with hydrophobicity.	2008 Oct 7	18795793
A structural and thermal investigation of the inclusion of parabens in heptakis(2,6-di-O-methyl)cyclomaltoheptaose.	2008 Sep 22	18662812
Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach.	2009 Jan	19063592

Patents

Sample Use Guides

In Vivo Use Guide

in rats: orally exposed to 0, 10, 100, or 500 mg/kg bw/d of butylparaben from gestation day 7 to pup day 22

Route of Administration: Oral

In Vitro Use Guide

It was evaluated the effects of di-(2-ethylhexyl) phthalate (DEHP) (ranging from 10(-9) to 10(-7) m [1-100 nm; 0.39-39 ng ml(-1) ]) and butylparaben (BP) (ranging from 10(-8) to 10(-5) m [10 nm-10 μm; 1.9 ng ml(-1) to 1.9 μg ml(-1) ]), alone and in combination, on isolated mouse preantral follicle and human granulosa cell (hGC) cultures to study direct effects on follicle growth and ovarian steroidogenesis. It was found that, in follicle culture, DEHP and BP attenuate estradiol output but only when present together. DEHP decreases progesterone concentrations in the spent media of hGC cultures, an effect that was attenuated when BP was added together with DEHP. Although changes in steroidogenesis were observed, no effects on follicular development or survival were noted in the culture systems

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:58:40 GMT 2025` Edited by `admin` on `Mon Mar 31 17:58:40 GMT 2025`
Record UNII	3QPI1U3FV8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTYL HYDROXYBENZOATE

Preferred Name

English

BUTYLPARABEN

Official Name

English

BUTYLPARABEN [USP-RS]

Common Name

English

BUTYLPARABEN [VANDF]

Common Name

English

FEMA NO. 2203

Code

English

BUTYLPARABEN [II]

Common Name

English

BUTYL P-HYDROXY BENZOATE

Common Name

English

BUTYLPARABEN [MI]

Common Name

English

BUTYL PARAHYDROXYBENZOATE

Systematic Name

English

BUTYL HYDROXYBENZOATE [MART.]

Common Name

English

BUTYL PARABEN

Common Name

English

Butyl hydroxybenzoate [WHO-DD]

Common Name

English

NSC-13164

Code

English

BUTYL PARAHYDROXYBENZOATE [EP MONOGRAPH]

Common Name

English

BUTYL PARAHYDROXYBENZOATE [JAN]

Common Name

English

METHYL PARAHYDROXYBENZOATE IMPURITY D [EP IMPURITY]

Common Name

English

BUTYLPARABEN [HSDB]

Common Name

English

BUTYL P-HYDROXY BENZOATE [FHFI]

Common Name

English

BUTYL PARAHYDROXYBENZOATE [EP IMPURITY]

Common Name

English

PROPYL HYDROXYBENZOATE IMPURITY D [EP IMPURITY]

Common Name

English

Butyl 4-hydroxybenzoate

Systematic Name

English

BENZOIC ACID, 4-HYDROXY-, BUTYL ESTER

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000185508