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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 of BUTYLPARABEN

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
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
PubMed

PubMed

TitleDatePubMed
Eco-friendly methodologies for the synthesis of some aromatic esters, well-known cosmetic ingredients.
2005 Feb
Parabens as urinary biomarkers of exposure in humans.
2006 Dec
Acceleration of paraben sorption to polyethylene terephthalate: a freeze-thaw phenomenon.
2006 Jul-Aug
Comparative study for the analysis of parabens by micellar electrokinetic capillary chromatography with and without large-volume sample stacking technique.
2006 Mar 15
The influence of physicochemical properties of preservative compounds on their distribution into various phases of oil in water submicron emulsion.
2006 May-Jun
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
Variability in human skin permeability in vitro: comparing penetrants with different physicochemical properties.
2007 Apr
Parabens inhibit human skin estrogen sulfotransferase activity: possible link to paraben estrogenic effects.
2007 Apr 11
[Simultaneous determination of 7 kinds of preservatives and saccharin in foods with HPLC, and identification with LC/MS/MS].
2007 Dec
Influence of crystal structure on the tableting properties of n-alkyl 4-hydroxybenzoate esters (parabens).
2007 Dec
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
Simultaneous determination of seven phthalates and four parabens in cosmetic products using HPLC-DAD and GC-MS methods.
2007 Jan
Comparison of the global gene expression profiles produced by methylparaben, n-butylparaben and 17beta-oestradiol in MCF7 human breast cancer cells.
2007 Jan-Feb
Simultaneous determination of antioxidants, preservatives and sweetener additives in food and cosmetics by flow injection analysis coupled to a monolithic column.
2007 Jul 2
[Simultaneous determination of nine kinds of preservatives in foods by HPLC].
2007 Jun
Investigating protein haptenation mechanisms of skin sensitisers using human serum albumin as a model protein.
2007 Jun
Antiandrogenic properties of parabens and other phenolic containing small molecules in personal care products.
2007 Jun 15
[Simultaneous determination of phthalates and parabens in cosmetic products by gas chromatography/mass spectrometry coupled with solid phase extraction].
2007 Mar
Comparison of objective and sensory skin irritations of several cosmetic preservatives.
2007 Mar
[Enhancement of di-n-butyl phthalate on the estrogenic activities of esters of p-hydroxybenzoic acid].
2007 May
Temporal stability of the conjugated species of bisphenol A, parabens, and other environmental phenols in human urine.
2007 Sep
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products.
2008
Urinary excretion of phthalates and paraben after repeated whole-body topical application in humans.
2008 Apr
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
Higher levels of ethyl paraben and butyl paraben in rat amniotic fluid than in maternal plasma after subcutaneous administration.
2008 Dec
Development of an in vitro test battery for assessing chemical effects on bovine germ cells under the ReProTect umbrella.
2008 Dec 15
Determination of parabens in environmental solid samples by ultrasonic-assisted extraction and liquid chromatography with triple quadrupole mass spectrometry.
2008 Dec 19
Skin protection creams in medical settings: successful or evil?
2008 Jul 25
Association of nicotinamide with parabens: effect on solubility, partition and transdermal permeation.
2008 Jun
Preparation and characterization of inclusion complexes of a cationic beta-cyclodextrin polymer with butylparaben or triclosan.
2008 Jun 5
[Application of single drop microextraction in the determination of phthalate esters and parabens in drugs by gas chromatography-mass spectrometry].
2008 May
Do parabens have the ability to interfere with steroidogenesis?
2008 Nov
Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography.
2008 Oct
The membrane lateral pressure-perturbing capacity of parabens and their effects on the mechanosensitive channel directly correlate with hydrophobicity.
2008 Oct 7
A structural and thermal investigation of the inclusion of parabens in heptakis(2,6-di-O-methyl)cyclomaltoheptaose.
2008 Sep 22
Impact of diisobutyl phthalate and other PPAR agonists on steroidogenesis and plasma insulin and leptin levels in fetal rats.
2008 Sep 4
The aqueous photosensitized degradation of butylparaben.
2009 Apr
Single-drop microextraction followed by in-syringe derivatization and GC-MS detection for the determination of parabens in water and cosmetic products.
2009 Apr
Short-term iontophoretic and post-iontophoretic transport of model penetrants across excised human epidermis.
2009 Feb 9
Comparison of artificial sebum with human and hamster sebum samples.
2009 Feb 9
[Butyl-p-hydroxybenzoate stimulates cystic fibrosis transmembrane conductance regulator Cl- transport].
2009 Jan
Identification of xenoestrogens in food additives by an integrated in silico and in vitro approach.
2009 Jan
Parabens in male infertility-is there a mitochondrial connection?
2009 Jan
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
Estrogenicity of parabens revisited: impact of parabens on early pregnancy and an uterotrophic assay in mice.
2009 Jul
Removal of estrogenic activity of iso-butylparaben and n-butylparaben by laccase in the presence of 1-hydroxybenzotriazole.
2009 Jul
Analysis of parabens in cosmetics by low pressure liquid chromatography with monolithic column and chemiluminescent detection.
2009 Jul 15
Relating solubility data of parabens in liquid PEG 400 to the behaviour of PEG 4000-parabens solid dispersions.
2009 Oct
Determination of ibudilast in human serum by high-performance liquid chromatography for pharmacokinetic study.
2010 Mar
Patents

Sample Use Guides

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
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
  • Download
Name Type Language
BUTYLPARABEN
HSDB   II   INCI   MI   USP-RS   VANDF  
INCI  
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
FHFI  
Common Name English
BUTYLPARABEN [MI]
Common Name English
BUTYL PARAHYDROXYBENZOATE
EP  
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
MART.   WHO-DD  
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
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
EPA PESTICIDE CODE 61205
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
NCI_THESAURUS C92608
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
JECFA EVALUATION BUTYL P-HYDROXYBENZOATE
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
Code System Code Type Description
DRUG BANK
DB14084
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
WIKIPEDIA
BUTYLPARABEN
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
ChEMBL
CHEMBL459008
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
MESH
C038091
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
PUBCHEM
7184
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
EVMPD
SUB11763MIG
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
NCI_THESAURUS
C76701
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
CAS
94-26-8
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
JECFA MONOGRAPH
1132
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
SMS_ID
100000076383
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
ECHA (EC/EINECS)
202-318-7
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
FDA UNII
3QPI1U3FV8
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY Increased Histamine Release [PE]
DAILYMED
3QPI1U3FV8
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
RXCUI
1306937
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID3020209
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
MERCK INDEX
m2857
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY Merck Index
HSDB
286
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
RS_ITEM_NUM
1084000
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
NSC
13164
Created by admin on Fri Dec 15 15:29:16 GMT 2023 , Edited by admin on Fri Dec 15 15:29:16 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY