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 235 Sources: https://www.drugs.com/imprints/barr-10-mg-876-1410.html	Inactive ingredient		Approved 8429	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 2578

PubMed

Title	Date	PubMed
Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients.	2005 Feb	18492177
Comparative study for the analysis of parabens by micellar electrokinetic capillary chromatography with and without large-volume sample stacking technique.	2006 Mar 15	18970549
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
Dose-response of the cultured bovine lens to butyl, methyl and propyl parabens.	2007 Apr	18489331
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
Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay.	2007 Dec	18174956
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	17889094
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
[Simultaneous determination of phthalates and parabens in cosmetic products by gas chromatography/mass spectrometry coupled with solid phase extraction].	2007 Mar	17580703
[Enhancement of di-n-butyl phthalate on the estrogenic activities of esters of p-hydroxybenzoic acid].	2007 May	17712932
Studies on the lipophilicity of vehicles (or co-vehicles) and botanical oils used in cosmetic products.	2007 May	17557742
Assessment of principal parabens used in cosmetics after their passage through human epidermis-dermis layers (ex-vivo study).	2007 Oct	17845215
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
Sunscreens cause coral bleaching by promoting viral infections.	2008 Apr	18414624
Lack of effect of butylparaben and methylparaben on the reproductive system in male rats.	2008 Apr	18393383
Urinary excretion of phthalates and paraben after repeated whole-body topical application in humans.	2008 Apr	18194284
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
Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration.	2008 Dec	18713765
Development of an in vitro test battery for assessing chemical effects on bovine germ cells under the ReProTect umbrella.	2008 Dec 15	18835402
Determination of parabens in environmental solid samples by ultrasonic-assisted extraction and liquid chromatography with triple quadrupole mass spectrometry.	2008 Dec 19	19010476
Electrospun polymer nanofibers as a solid-phase extraction sorbent for the determination of trace pollutants in environmental water.	2008 Feb	18066539
On-line pretreatment and determination of parabens in cosmetic products by combination of flow injection analysis, solid-phase extraction and micellar electrokinetic chromatography.	2008 Feb 15	18371792
Genotoxic effects of environmental estrogen-like compounds in CHO-K1 cells.	2008 Jan 8	17913570
Skin protection creams in medical settings: successful or evil?	2008 Jul 25	18655702
Association of nicotinamide with parabens: effect on solubility, partition and transdermal permeation.	2008 Jun	18207718
Preparation and characterization of inclusion complexes of a cationic beta-cyclodextrin polymer with butylparaben or triclosan.	2008 Jun 5	18294789
Effect of abrasion induced by a rotating brush on the skin permeation of solutes with varying physicochemical properties.	2008 Mar	17618097
[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
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.	2008 Oct	18822043
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
Impact of diisobutyl phthalate and other PPAR agonists on steroidogenesis and plasma insulin and leptin levels in fetal rats.	2008 Sep 4	18602967
The aqueous photosensitized degradation of butylparaben.	2009 Apr	19337670
Single-drop microextraction followed by in-syringe derivatization and GC-MS detection for the determination of parabens in water and cosmetic products.	2009 Apr	19266549
Short-term iontophoretic and post-iontophoretic transport of model penetrants across excised human epidermis.	2009 Feb 9	18950696
Comparison of artificial sebum with human and hamster sebum samples.	2009 Feb 9	18929636
[Butyl-p-hydroxybenzoate stimulates cystic fibrosis transmembrane conductance regulator Cl- transport].	2009 Jan	19350818
Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach.	2009 Jan	19063592
Parabens in male infertility-is there a mitochondrial connection?	2009 Jan	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 Jan	18717622
Estrogenicity of parabens revisited: impact of parabens on early pregnancy and an uterotrophic assay in mice.	2009 Jul	19490991
Removal of estrogenic activity of iso-butylparaben and n-butylparaben by laccase in the presence of 1-hydroxybenzotriazole.	2009 Jul	19109757
Analysis of parabens in cosmetics by low pressure liquid chromatography with monolithic column and chemiluminescent detection.	2009 Jul 15	19559911
Relating solubility data of parabens in liquid PEG 400 to the behaviour of PEG 4000-parabens solid dispersions.	2009 Oct	19508891
Determination of ibudilast in human serum by high-performance liquid chromatography for pharmacokinetic study.	2010 Mar	19629961

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 `Fri Dec 15 15:29:16 GMT 2023` Edited by `admin` on `Fri Dec 15 15:29:16 GMT 2023`
Record UNII	3QPI1U3FV8
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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 HYDROXYBENZOATE

Systematic Name

English

BUTYLPARABEN [INCI]

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