BUTYLPARABEN SODIUM

First approved in 1984

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13O3.Na
Molecular Weight	216.2089
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=OGBHACNFHJJTQT-UHFFFAOYSA-M

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

HIDE SMILES / InChI

Molecular Formula	C11H13O3
Molecular Weight	193.2191
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
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
Determination of ibudilast in human serum by high-performance liquid chromatography for pharmacokinetic study.	2010-03	19629961
Relating solubility data of parabens in liquid PEG 400 to the behaviour of PEG 4000-parabens solid dispersions.	2009-10	19508891
Analysis of parabens in cosmetics by low pressure liquid chromatography with monolithic column and chemiluminescent detection.	2009-07-15	19559911
Estrogenicity of parabens revisited: impact of parabens on early pregnancy and an uterotrophic assay in mice.	2009-07	19490991
Removal of estrogenic activity of iso-butylparaben and n-butylparaben by laccase in the presence of 1-hydroxybenzotriazole.	2009-07	19109757
The aqueous photosensitized degradation of butylparaben.	2009-04	19337670
Single-drop microextraction followed by in-syringe derivatization and GC-MS detection for the determination of parabens in water and cosmetic products.	2009-04	19266549
Short-term iontophoretic and post-iontophoretic transport of model penetrants across excised human epidermis.	2009-02-09	18950696
Comparison of artificial sebum with human and hamster sebum samples.	2009-02-09	18929636
[Butyl-p-hydroxybenzoate stimulates cystic fibrosis transmembrane conductance regulator Cl- transport].	2009-01	19350818
Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach.	2009-01	19063592
Parabens in male infertility-is there a mitochondrial connection?	2009-01	19007877
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	18717622
Determination of parabens in environmental solid samples by ultrasonic-assisted extraction and liquid chromatography with triple quadrupole mass spectrometry.	2008-12-19	19010476
Development of an in vitro test battery for assessing chemical effects on bovine germ cells under the ReProTect umbrella.	2008-12-15	18835402
Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration.	2008-12	18713765
Do parabens have the ability to interfere with steroidogenesis?	2008-11	18648085
The membrane lateral pressure-perturbing capacity of parabens and their effects on the mechanosensitive channel directly correlate with hydrophobicity.	2008-10-07	18795793
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008-10	18822043
A structural and thermal investigation of the inclusion of parabens in heptakis(2,6-di-O-methyl)cyclomaltoheptaose.	2008-09-22	18662812
Impact of diisobutyl phthalate and other PPAR agonists on steroidogenesis and plasma insulin and leptin levels in fetal rats.	2008-09-04	18602967
Analysis and quantification of parabens in cosmetic products by utilizing hollow fibre-supported liquid membrane and high performance liquid chromatography with ultraviolet detection.	2008-08	18713076
Skin protection creams in medical settings: successful or evil?	2008-07-25	18655702
Preparation and characterization of inclusion complexes of a cationic beta-cyclodextrin polymer with butylparaben or triclosan.	2008-06-05	18294789
Association of nicotinamide with parabens: effect on solubility, partition and transdermal permeation.	2008-06	18207718
[Application of single drop microextraction in the determination of phthalate esters and parabens in drugs by gas chromatography-mass spectrometry].	2008-05	18724664
Sunscreens cause coral bleaching by promoting viral infections.	2008-04	18414624
Lack of effect of butylparaben and methylparaben on the reproductive system in male rats.	2008-04	18393383
Urinary excretion of phthalates and paraben after repeated whole-body topical application in humans.	2008-04	18194284
Effect of abrasion induced by a rotating brush on the skin permeation of solutes with varying physicochemical properties.	2008-03	17618097
On-line pretreatment and determination of parabens in cosmetic products by combination of flow injection analysis, solid-phase extraction and micellar electrokinetic chromatography.	2008-02-15	18371792
Electrospun polymer nanofibers as a solid-phase extraction sorbent for the determination of trace pollutants in environmental water.	2008-02	18066539
Genotoxic effects of environmental estrogen-like compounds in CHO-K1 cells.	2008-01-08	17913570
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products.	2008	19101832
Percutaneous permeation enhancement by terpenes: mechanistic view.	2008	18446512
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	17889094
[Simultaneous determination of 7 kinds of preservatives and saccharin in foods with HPLC, and identification with LC/MS/MS].	2007-12	18203501
Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay.	2007-12	18174956
Assessment of principal parabens used in cosmetics after their passage through human epidermis-dermis layers (ex-vivo study).	2007-10	17845215
Systemic uptake of diethyl phthalate, dibutyl phthalate, and butyl paraben following whole-body topical application and reproductive and thyroid hormone levels in humans.	2007-08-01	17822133
Simultaneous determination of antioxidants, preservatives and sweetener additives in food and cosmetics by flow injection analysis coupled to a monolithic column.	2007-07-02	17586119
[Simultaneous determination of nine kinds of preservatives in foods by HPLC].	2007-06	17657998
[Enhancement of di-n-butyl phthalate on the estrogenic activities of esters of p-hydroxybenzoic acid].	2007-05	17712932
Studies on the lipophilicity of vehicles (or co-vehicles) and botanical oils used in cosmetic products.	2007-05	17557742
Dose-response of the cultured bovine lens to butyl, methyl and propyl parabens.	2007-04	18489331
[Simultaneous determination of phthalates and parabens in cosmetic products by gas chromatography/mass spectrometry coupled with solid phase extraction].	2007-03	17580703
Preliminary ecological risk assessment of butylparaben and benzylparaben -2. Fate and partitioning in aquatic environments.	2007	18382418
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
Comparative study for the analysis of parabens by micellar electrokinetic capillary chromatography with and without large-volume sample stacking technique.	2006-03-15	18970549
Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients.	2005-02	18492177

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 18:13:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:13:38 GMT 2025`
Record UNII	MAR76J77VS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BUTYLPARABEN SODIUM

Common Name

English

SODIUM BUTYLPARABEN

Preferred Name

English

SODIUM BUTYL HYDROXYBENZOATE [MART.]

Common Name

English

SODIUM BUTYL HYDROXYBENZOATE

Systematic Name

English

BENZOIC ACID, 4-HYDROXY-, BUTYL ESTER, SODIUM SALT (1:1)

Systematic Name

English

BUTYL-4-HYDROXYBENZOATE SODIUM SALT

Common Name

English

P-HYDROXYBENZOIC ACID BUTYL ESTER SODIUM SALT

Common Name

English

BUTYL PARAHYDROXYBENZOATE SODIUM

Systematic Name

English

BUTYL 4-HYDROXYBENZOATE SODIUM SALT

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C92608