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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
The influence of type and quantity of model drug on the extrusion/spheronization of mixtures with microcrystalline cellulose. I. Extrusion parameters.
2001 Apr 17
A fast and efficient determination of amines and preservatives in cough and cold liquid and suspension formulations using a single isocratic ion-pairing high performance [correction of power] liquid chromatography method.
2001 Aug
ER-dependent estrogenic activity of parabens assessed by proliferation of human breast cancer MCF-7 cells and expression of ERalpha and PR.
2001 Dec
Effects of butylparaben on the male reproductive system in rats.
2001 Feb
Controlled drug release from gels using surfactant aggregates: I. Effect of lipophilic interactions for a series of uncharged substances.
2001 Sep
Oestrogenic activity of parabens in MCF7 human breast cancer cells.
2002 Jan
Effects of butyl paraben on the male reproductive system in mice.
2002 Jul
Additive estrogenic activities of the binary mixtures of four estrogenic chemicals in recombinant yeast expressing human estrogen receptor.
2002 Mar
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.
2002 Nov 15
Determination of cisapride, its oxidation product, propyl and butyl parabens in pharmaceutical dosage form by reversed-phase liquid chromatography.
2003 Dec 4
Developmental toxicity evaluation of butylparaben in Sprague-Dawley rats.
2004 Aug
Separation of preservatives in cosmetic products by micellar electrokinetic chromatography.
2004 Dec
Biotransformation of chlorpropham (CIPC) in isolated rat hepatocytes and xenoestrogenic activity of CIPC and its metabolites by in vitro assays.
2004 Mar
A review of the endocrine activity of parabens and implications for potential risks to human health.
2005 Jun
Decrease in skin permeation and antibacterial effect of parabens by a polymeric additive, poly(2-methacryloyloxyethyl phosphorylcholine-co-butylmetacrylate).
2005 Mar
Determination of parabens in pharmaceutical formulations by solid-phase microextraction-ion mobility spectrometry.
2005 Sep 15
Practical constraints in the kinetic plot representation of chromatographic performance data: theory and application to experimental data.
2006 Apr 1
Simultaneous analysis of antioxidants and preservatives in cosmetics by supercritical fluid extraction combined with liquid chromatography-mass spectrometry.
2006 Jul 7
Acceleration of paraben sorption to polyethylene terephthalate: a freeze-thaw phenomenon.
2006 Jul-Aug
Effector-repressor interactions, binding of a single effector molecule to the operator-bound TtgR homodimer mediates derepression.
2006 Mar 17
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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Parabens inhibit human skin estrogen sulfotransferase activity: possible link to paraben estrogenic effects.
2007 Apr 11
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
Simultaneous determination of seven phthalates and four parabens in cosmetic products using HPLC-DAD and GC-MS methods.
2007 Jan
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
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
[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
Development of an in vitro test battery for assessing chemical effects on bovine germ cells under the ReProTect umbrella.
2008 Dec 15
Effect of abrasion induced by a rotating brush on the skin permeation of solutes with varying physicochemical properties.
2008 Mar
[Application of single drop microextraction in the determination of phthalate esters and parabens in drugs by gas chromatography-mass spectrometry].
2008 May
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
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
Parabens in male infertility-is there a mitochondrial connection?
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
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