butylparaben

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Butylparaben - Butyl P-Hydroxybenzoate

Butylparaben, or butyl paraben, is a member of the paraben family, which has the formula

C4H9(C6H4(OH)COO). It is used as an antimicrobial preservative in cosmetics such as eye shadow,

foundation, sunscreen, facial moisturizer and skin anti-aging treatment. It is also used in medicationsuspensions, and as a flavoring additive in food. Butylparaben and the paraben family have come to

public attention recently, due to a study reporting low concentrations of parabens in breast tumors,

around 20.6 4.2 ng/g tissue. However, parabens have not been proven to cause breast cancer.

Estimates by the U.S. Food and Drug Administration and the Center for Food Safety and Applied

Nutrition have found that the average person is exposed to about 37 ng of butylparaben per day.

Contents

1 Properties:

2 Occurrence:

3 Preparation:

4 Uses and Reactions:

5 History:

6 Safety and Toxicology:

o 6.1 Endocrine Disruption

o 6.2 Antiandrogenic

o 6.3 Carcinogenicity

o 6.4 Ongoing/Future Research

7 Notes:

Butylparaben

IUPAC name
http://en.wikipedia.org/wiki/Butylparaben#Properties:http://en.wikipedia.org/wiki/Butylparaben#Properties:http://en.wikipedia.org/wiki/Butylparaben#Occurrence:http://en.wikipedia.org/wiki/Butylparaben#Occurrence:http://en.wikipedia.org/wiki/Butylparaben#Preparation:http://en.wikipedia.org/wiki/Butylparaben#Preparation:http://en.wikipedia.org/wiki/Butylparaben#Uses_and_Reactions:http://en.wikipedia.org/wiki/Butylparaben#Uses_and_Reactions:http://en.wikipedia.org/wiki/Butylparaben#History:http://en.wikipedia.org/wiki/Butylparaben#History:http://en.wikipedia.org/wiki/Butylparaben#Safety_and_Toxicology:http://en.wikipedia.org/wiki/Butylparaben#Safety_and_Toxicology:http://en.wikipedia.org/wiki/Butylparaben#Endocrine_Disruptionhttp://en.wikipedia.org/wiki/Butylparaben#Endocrine_Disruptionhttp://en.wikipedia.org/wiki/Butylparaben#Antiandrogenichttp://en.wikipedia.org/wiki/Butylparaben#Antiandrogenichttp://en.wikipedia.org/wiki/Butylparaben#Carcinogenicityhttp://en.wikipedia.org/wiki/Butylparaben#Carcinogenicityhttp://en.wikipedia.org/wiki/Butylparaben#Ongoing.2FFuture_Researchhttp://en.wikipedia.org/wiki/Butylparaben#Ongoing.2FFuture_Researchhttp://en.wikipedia.org/wiki/Butylparaben#Notes:http://en.wikipedia.org/wiki/Butylparaben#Notes:http://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/File:Butylparaben.svghttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/Butylparaben#Notes:http://en.wikipedia.org/wiki/Butylparaben#Ongoing.2FFuture_Researchhttp://en.wikipedia.org/wiki/Butylparaben#Carcinogenicityhttp://en.wikipedia.org/wiki/Butylparaben#Antiandrogenichttp://en.wikipedia.org/wiki/Butylparaben#Endocrine_Disruptionhttp://en.wikipedia.org/wiki/Butylparaben#Safety_and_Toxicology:http://en.wikipedia.org/wiki/Butylparaben#History:http://en.wikipedia.org/wiki/Butylparaben#Uses_and_Reactions:http://en.wikipedia.org/wiki/Butylparaben#Preparation:http://en.wikipedia.org/wiki/Butylparaben#Occurrence:http://en.wikipedia.org/wiki/Butylparaben#Properties:


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butyl 4-hydroxybenzoate

Other names

butyl paraben;

butyl parahydroxybenzoate;

butyl p-hydroxybenzoate

Identifiers

CAS number 94-26-8

PubChem 7184

ChemSpider 6916

UNII 3QPI1U3FV8

KEGG D01420

ChEMBL CHEMBL459008

Jmol-3D images Image 1

SMILES

[show]

InChI

[show]

Properties

Molecular formula C11H14O3

Molar mass 194.227 g/mol
http://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/International_Union_of_Pure_and_Applied_Chemistry_nomenclaturehttp://en.wikipedia.org/wiki/CAS_registry_numberhttp://en.wikipedia.org/wiki/CAS_registry_numberhttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=94-26-8http://www.commonchemistry.org/ChemicalDetail.aspx?ref=94-26-8http://en.wikipedia.org/wiki/PubChemhttp://en.wikipedia.org/wiki/PubChemhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7184http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7184http://en.wikipedia.org/wiki/ChemSpiderhttp://en.wikipedia.org/wiki/ChemSpiderhttp://www.chemspider.com/6916http://www.chemspider.com/6916http://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=3QPI1U3FV8http://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=3QPI1U3FV8http://en.wikipedia.org/wiki/KEGGhttp://en.wikipedia.org/wiki/KEGGhttp://www.kegg.jp/entry/D01420http://www.kegg.jp/entry/D01420http://en.wikipedia.org/wiki/ChEMBLhttp://en.wikipedia.org/wiki/ChEMBLhttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL459008https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL459008http://en.wikipedia.org/wiki/Jmolhttp://en.wikipedia.org/wiki/Jmolhttp://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28OCCCC%29c1ccc%28O%29cc1http://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28OCCCC%29c1ccc%28O%29cc1http://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://en.wikipedia.org/wiki/International_Chemical_Identifierhttp://en.wikipedia.org/wiki/International_Chemical_Identifierhttp://en.wikipedia.org/wiki/Chemical_formulahttp://en.wikipedia.org/wiki/Chemical_formulahttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Molar_masshttp://en.wikipedia.org/wiki/Chemical_formulahttp://en.wikipedia.org/wiki/International_Chemical_Identifierhttp://en.wikipedia.org/wiki/Simplified_molecular_input_line_entry_specificationhttp://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DC%28OCCCC%29c1ccc%28O%29cc1http://en.wikipedia.org/wiki/Jmolhttps://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL459008http://en.wikipedia.org/wiki/ChEMBLhttp://www.kegg.jp/entry/D01420http://en.wikipedia.org/wiki/KEGGhttp://fdasis.nlm.nih.gov/srs/srsdirect.jsp?regno=3QPI1U3FV8http://en.wikipedia.org/wiki/Unique_Ingredient_Identifierhttp://www.chemspider.com/6916http://en.wikipedia.org/wiki/ChemSpiderhttp://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=7184http://en.wikipedia.org/wiki/PubChemhttp://www.commonchemistry.org/ChemicalDetail.aspx?ref=94-26-8http://en.wikipedia.org/wiki/CAS_registry_number


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Appearance colorless, odorless, crystalline powder

Melting point 68-69C

Solubilityinwater acetone, ethanol, chloroform, glycerin, propylene glycol, slightly soluble in

H2O

Related compounds

Related compounds Paraben

Ethylparaben

Methylparaben

Propylparaben

Properties:

Butylparaben is a fine, colorless, odorless, crystalline solid at room temperature. The molecular formula of

butylparaben is C11H14O3; its molecular weight is 194.227 g/mol. Butylparaben is soluble in acetone,

ethanol, and chloroform, and slightly soluble in H2O.[8]

It has a melting point of 68-69C and

undergoes hydrolysis to its corresponding carboxylic acid in basic solutions. The antimicrobial activity

ofparabensincreases with increasing alkyl chain length

(methylparaben


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Preparation:

Butylparaben is prepared by the esterification of 4-Hydroxybenzoic acid with 1-butanol in the presence of

an acid catalyst, such as sulfuric acid. It is available for commercial purchase from a number of different

distributors, including Ashland Inc., J.T. Baker, and Penta Manufacturing Co.

Uses and Reactions:

Butylparaben is one of the most commonplace bactericidal/fungicidal additives to cosmetics, probably

due to its low cost, and efficiency as a microbial agent. It is reported by the EWG to be found in almost

3000 cosmetic products including eye shadow, facial moisturizer/treatment, anti-aging cream, foundation,

and sunscreen. In most cosmetics paraben is used at low levels, ranging from 0.01 to 0.3%. Numerous

members of the paraben family are found in fruit and vegetable products, such as barley, flax seed, and

grapes. Butylparaben can also be found in low concentrations in liquid and solid medication suspensions,

such as tylenol (acetaminophen) and ibuprofen. In the paraben family, butylparaben appears to be the

best antifungal agent. It is particularly active against molds and yeasts, and less active against bacteria.

History:Butylparaben has been used in cosmetic products for over 80 years. Its use in pharmaceutical products

has occurred since 1924. In December 2010 the Scientific Committee on Consumer Products (SCCP) of

the European Union published that there is not enough data to perform risk assessments for butylparaben

in humans.]Despite this publishing, Denmark banned butylparaben in products for use by children

younger than tthe age of three, in March of 2011. Butylparaben is presently regulated by the U.S. Food

and Drug Administration as a synthetic flavoring and adjuvant. It is recommended that it be used in the

minimum amount necessary to achieve its intended effect. Butylparaben is also regulated by the United

States Environmental Protection Agency under theToxic Substances Control Act of 1976 and the Federal

Insecticide, Fungicide, and Rodenticide Act. Its pesticide registration was canceled in 1998.

Safety and Toxicology:

Exposure to butylparaben can occur via inhalation, ingestion and eye or skin contact. Ingestion is not

considered a safety concern because butylparaben is quickly absorbed, metabolized and excreted.

Evidence of the absorbance of butylparaben through the skin, however, has shown that it can last much

longer, and accumulate in epithelial tissue. In mice, the Median lethal dose (LD50) is about 5000 mg/kg

body weight.

Endocrine Disruption

Butylparaben is estrogenic, meaning it mimics natural estrogen in the body. For example, parabens can

bind to estrogen receptors and regulate estrogen responsive gene products in experimental cell

systems. Long-chained parabens, like butylparaben, are more estrogenic than short-chained parabens,

like methyl- or ethylparaben. This is likely because long-chained parabens are more

lipophilic/hydrophobic, and have a higher affinity for estrogen receptors.

Antiandrogenic

Butylparaben can decrease sperm function and alter metabolic hormones. Rats exposed to a high

concentration of butylparaben during pregnancy gave birth to fewer pups, and pups with malformed
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reproductive organs. A study on humans has found that reduced sperm counts and functional

abnormalities in sperm are associated with elevated levels of butylparaben.

Carcinogenicity

Butylparaben has been found in small concentrations in human breast fat and breast tumors.A study by

Darbre et al. (2004) has suggested that the underarm application of paraben-containing deodorants mayattribute to breast cancer. Oral administration of butylparaben to eight-week-old rats has caused tumors

such as thymic lymphoma, non-thymic lyphoid leukemia, and myeloid leukemia. Similar studies, however,

have found no significant increase in tumors upon butylparaben administration. The carcinogenicity of

butylparaben is currently listed as "possible" on the EWG website.

Ongoing/Future Research

Butylparaben is not considered to be a safety risk at this time for many governmental agencies around

the world, but it is under close scrutiny, and the subject of ongoing research. TheCosmetic Ingredient

Review (CIR), an industry sponsored organization under the FDA that encourages researchers to submit

their work, has reopened their safety assessment for parabens. The organization reviews and publishes

credible research, and looks to answer the following questions: Is there a causal link between breastcancer and parabens? What are the concentrations of paraben that cause acute and chronic harm? Are

there reproductive malformations caused by paraben exposure? These questions and more are looking to

be answered with the implementation of new research techniques and resources.

butylparaben

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