Butylparaben
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| Names |
| IUPAC name
Butyl 4-hydroxybenzoate
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Other names
Butyl paraben;
Butyl parahydroxybenzoate;
Butyl p-hydroxybenzoate |
| Identifiers |
|
CAS Number
|
94-26-8 Y |
| ChEMBL |
ChEMBL459008 Y |
| ChemSpider |
6916 Y |
InChI
-
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 Y
Key: QFOHBWFCKVYLES-UHFFFAOYSA-N Y
-
InChI=1/C11H14O3/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7,12H,2-3,8H2,1H3
Key: QFOHBWFCKVYLES-UHFFFAOYAN
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| Jmol interactive 3D |
Image |
| KEGG |
D01420 Y |
| PubChem |
7184 |
|
|
| UNII |
3QPI1U3FV8 Y |
| Properties |
|
Chemical formula
|
C11H14O3 |
| Molar mass |
194.23 g·mol−1 |
| Appearance |
Colorless, odorless, crystalline powder |
| Melting point |
68 to 69 °C (154 to 156 °F; 341 to 342 K) |
|
Solubility in water
|
Slightly soluble |
| Solubility in acetone, ethanol, chloroform, glycerin, propylene glycol |
Soluble |
| Hazards |
| NFPA 704 |
|
| Related compounds |
|
Related compounds
|
Paraben
Ethylparaben
Methylparaben
Propylparaben |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
| Y verify (what is YN ?) |
| Infobox references |
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Butylparaben, or butyl paraben, is an organic compound with the formula C
4H
9O
2CC
6H
4OH.[1] It is a white solid that is soluble in organic solvents. It has proven to be a highly successful antimicrobial preservative in cosmetics.[2] It is also used in medication suspensions, and as a flavoring additive in food.
Contents
- 1 Occurrence
- 2 Preparation
- 3 Uses and reactions
- 4 Regulation and controversy
- 4.1 Regulation
- 4.2 Endocrine disruption
- 4.3 Antiandrogenic
- 4.4 Other
- 5 Notes
Occurrence
Members of the paraben family are found in fruit and vegetable products, such as barley, flax seed, and grapes.[3] Butylparaben can also be found in low concentrations in liquid and solid medication suspensions, such as tylenol (acetaminophen) and ibuprofen.[4] Butylparaben can also be found in the sewage. A 2001 study found that concentrations of parabens in Danish sewage facilities was to 100 to 1000 times below the acute or chronic effect concentrations.[5]
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.[6] It is produced industrially.
Uses and reactions
Butylparaben is one of the most common bactericidal/fungicidal additives in cosmetics. It has been used in cosmetic products since the 1940s and in pharmaceutical products since 1924.[7] The popularity of butylparaben in these products is due to its low toxicity in humans and its effective antimicrobial properties, in particular those against mold and yeast.[8] It is now found in more than 20,000 cosmetic products including eye shadow, facial moisturizer/treatment, anti-aging cream, foundation, and sunscreen.[9] It is also used as low-ionic strength solutions as a preservative in some foods and drugs.[10] In most cosmetics paraben is used at low levels, ranging from 0.01 to 0.3%.[11]
Mechanism of action
The exact mechanism of how parabens work is unknown but they are proposed to act by inhibiting DNA and RNA synthesis, and enzymes like ATPase and phosphotransferase in some bacterial species. It has also been suggested that they interfere with membrane transport processes by disrupting the lipid bylayer and possibly causing the leakage of intracellular constituents.[12]
Regulation and controversy
Butylparaben has not escaped controversy, which itself is controversial.[13][14] [15]
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.[16]
Regulation
Denmark restricts butylparaben in products for use by children younger than the age of three.[17]
In 2003, butylparaben was approved for use as a flavor additive in food by the U.S. Food and Agriculture Organization and the World Health Organization.[18][19] Butylparaben is also regulated by the United States Environmental Protection Agency under the U.S. Toxic Substances Control Act of 1976 and the Federal Insecticide, Fungicide, and Rodenticide Act. Its pesticide registration was canceled in 1998.[20]
Endocrine disruption
Butylparaben is weakly 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.[21] Long-chained parabens, like butylparaben, are more estrogenic than short-chained parabens, like methyl- or ethylparaben. This difference is attributed to the greater lipophilicity of the former.[22] A scientific review found that butylparaben displayed the most competitive binding to rat estrogen receptors when tested along with methyl, ethyl, and propylparabens. [23]
Antiandrogenic
Butylparaben can decrease sperm function and alter metabolic hormones.[24] Rats exposed to a high concentration of butylparaben during pregnancy gave birth to fewer pups, and pups with malformed reproductive organs.[25] Mice administered butylparaben at 0.01-1% body weight for ten weeks showed a decrease in serum testosterone concentration and in spermatid counts in the seminiferous tubules.[26] A study on humans has found that reduced sperm counts and functional abnormalities in sperm are associated with elevated levels of butylparaben.[27] To date, no antiandrogen mechanisms have been found for any of these experimental systems.
Other
It has been shown that butylparaben has the ability to cross body barriers, and enter the body through the lungs, GI tract, and skin epithelium.[28]
It occurs in breast cancers at around 7001206000000000000♠20.6±4.2 ng/g tissue.[29] However, parabens have not been proven to cause breast cancer.[30] 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.[31]
Butylparaben has been found in small concentrations in human breast fat and breast tumors.[32] A review by the National Toxicology Program concluded, "There is no evidence of demonstrable risk for the development of breast cancer caused by the use of paraben-containing underarm cosmetics."[33] Animal studies have been inconclusive. Oral administration of butylparaben to eight-week-old rats has caused tumors such as thymic lymphoma, non-thymic lyphoid leukemia, and myeloid leukemia.[34] Similar studies, however, have found no significant increase in tumors upon butylparaben administration.[35] Butylparaben is not listed as a carcinogen by the International Agency for Research on Cancer.[36]
Notes
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ Philip A. Geis "Preservation strategies" in "Cosmetic Microbiology, A Practical Approach" Edited by Philip A. Geis, CRC Press 2006. Pages 163–180, Print ISBN 978-0-8493-1453-7, eBook ISBN 978-1-4200-0332-1 doi:10.3109/9781420003321-12
- ^ "Parabens". Vashon Organics. Retrieved 2011-10-31.
- ^ "Ibuprofen Suspension". FreshPatents.com. Retrieved 2011-10-31.
- ^ "The Royal Danish School of Pharmacology Annual Report 2001" (PDF). The Royal Danish School of Pharmacology. 2001.
- ^ "Butylparaben". Hazardous Substance Data Bank. 2004-2.
- ^ "Parabens as Preservatives" (PDF). UENO FINE CHEMICALS INDUSTRY LTD. Retrieved 2011-10-31.
- ^ "Parabens as Preservatives" (PDF). UENO FINE CHEMICALS INDUSTRY LTD. Retrieved 2011-10-31.
- ^ Anon, "Final Amended Report on the Safety Assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in Cosmetic Products", Int. J. Toxicol. 2008, 27, 1.
- ^ "Butylparaben". Hazardous Substance Data Bank. 2004-2.
- ^ "Parabens". U.S. Food and Drug Administration. Retrieved 2011-10-31.
- ^ "Hydrolysis of 4-Hydroxybenzoic Acid Esters (Parabens) and Their Aerobic Transformation into Phenol by the Resistant Enterobacter cloacae Strain EM". Applied and Environmental Microbiology. June 2001.
- ^ Castelain, F., Castelain, M., "Parabens: a real hazard or a scare story?", Eur. J. Dermatol. 2012, 22, 723. doi:10.1684/ejd.2012.1835
- ^ "Parabens". U.S. Food and Drug Administration. Retrieved 2011-10-31.
- ^ "EWG's Skin Deep Cosmetics Database". Environmental Working Group. Retrieved 2011-10-31.
- ^ "Parabens used in personal care products and cosmetics". Chem Sec International. Retrieved 2011-10-31.
- ^ "Parabens used in personal care products and cosmetics". Chem Sec International. Retrieved 2011-10-31.
- ^ "35th Session of the Codex Committee on Food Labeling". Biodiversity Policy and Practice. 2003.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Parabens used in personal care products and cosmetics". Chem Sec International. Retrieved 2011-10-31.
- ^ "Pharmaceuticals and Personal Care Products in the Environment: Agents of Subtle Change?" (PDF). Environmental Health Perspectives. Retrieved 2015-02-08.
- ^ "Parabens used in personal care products and cosmetics". Chem Sec International. Retrieved 2011-10-31.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Chemicals in cosmetics, moisturizers linked to DNA damage in human sperm". Environmental Health News. Retrieved 2011-10-31.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Parabens". U.S. Food and Drug Administration. Retrieved 2011-10-31.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben [CAS No. 94-26-8]: Review of Toxicological Literature" (PDF). National Toxicology Program, National Institutes of Health. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Butylparaben Review of Toxicological Literature" (PDF). National Toxicological Program. April 2005.
- ^ "Agents Classified by the IARC Monographs, Volumes 1–109" (PDF). International Agency for Research on Cancer.
