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Revision as of 10:56, 25 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit		Latest revision as of 17:49, 11 September 2024 edit undoCitation bot (talk | contribs)Bots5,431,128 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Abductive | Category:E-number additives | #UCB_Category 290/313
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			{{short description|Chemical compound}}
	{{About|this particular compound|the class of hydroxybenzoate esters, including discussion on possible health effects|paraben}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 402497789
			| Watchedfields = changed
⚫	| ImageFileL1 = Hydroxypropyltrimonium.svg
		⚫	| verifiedrevid = 415845418
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
		⚫	| ImageFileL1 = methylparaben.svg
	| ImageSizeL1 = 150px		| ImageSizeL1 = 150px
	| ImageFileR1 = Methylparaben.png		| ImageFileR1 = Methylparaben.png
	| ImageSizeR1 = 100px		| ImageSizeR1 = 100px
	| IUPACName = Methyl 4-hydroxybenzoate		| PIN = Methyl 4-hydroxybenzoate
	| OtherNames = Methyl paraben;<br />Methyl ''p''-hydroxybenzoate;<br />Methyl parahydroxybenzoate;<br />Nipagin M;<br />] E218; Tegosept; Mycocten		| OtherNames = {{Unbulleted list|Methyl paraben|Methyl ''p''-hydroxybenzoate|Methyl parahydroxybenzoate|Nipagin M|] E218|Tegosept|Mycocten}}
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 6273
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7176		| ChemSpiderID = 7176
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = A2I8C7HI9T		| UNII = A2I8C7HI9T
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D01400		| KEGG = D01400
	| InChI = 1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3		| InChI = 1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
	| InChIKey = LXCFILQKKLGQFO-UHFFFAOYAH		| InChIKey = LXCFILQKKLGQFO-UHFFFAOYAH
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 31835
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 325372		| ChEMBL = 325372
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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	| CASNo = 99-76-3		| CASNo = 99-76-3
	| PubChem = 7456		| PubChem = 7456
	| SMILES = COC(=O)c1ccc(cc1)O		| SMILES = COC(=O)c1ccc(O)cc1
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=8|H=8|O=3		| C=8 | H=8 | O=3
			| Appearance = Colorless crystals or white crystalline powder<ref>{{cite web | url = https://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties | title = Methylparaben Experimental Properties | work = PubChem}}</ref>
	| Appearance =
	| Density =		| Density =
			| LambdaMax = 255{{nbsp}}nm (methanol)
	| MeltingPt =		| MeltingPt =
	| BoilingPt =		| BoilingPt =
	| Solubility = }}		| Solubility =
			| MagSus = −88.7·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol
⚫	| Section3 = {{Chembox Hazards
			}}
		⚫	|Section3={{Chembox Hazards
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
			| AutoignitionPt =
	| Autoignition = }}
			| NFPA-H = 1
⚫	| Section8 = {{Chembox Related
	| OtherAnions =		| NFPA-F = 1
	| OtherCations =		| NFPA-R = 0
			}}
⚫	| Function = ]s
		⚫	|Section8={{Chembox Related
⚫	| OtherFunctn = ]<br />]<br />]
			| OtherAnions =
⚫	| OtherCpds = ] (''ortho'' isomer)
			| OtherCations =
		⚫	| OtherFunction_label = ]s
		⚫	| OtherFunction = ]<br />]<br />]
		⚫	| OtherCompounds = ] (''ortho'' isomer)
	}}		}}
	}}		}}
			]
	'''Methylparaben''', also '''methyl paraben''', one of the ], is a preservative with the chemical formula CH<sub>3</sub>(C<sub>6</sub>H<sub>4</sub>(OH)COO). It is the ] ] of ].		'''Methylparaben''' ('''methyl paraben''') one of the ], is a preservative with the chemical formula CH<sub>3</sub>(C<sub>6</sub>H<sub>4</sub>(OH)COO). It is the ] ] of ].
			== Natural occurrences ==
	==Uses==
			Methylparaben serves as a ] for a variety of insects<ref>{{cite web | url = http://www.pherobase.com/database/compound/compounds-detail-me-4-hydroxybenzoate.php | title = Semiochemical - me-4-hydroxybenzoate | work = pherobase.com }}</ref> and is a component of ].
⚫	Methylparaben is an anti-fungal agent often used in a variety of cosmetics and personal care products. It is also used as a food preservative and has the ] E218.
			It is a pheromone in wolves produced{{clarify|reason=produced by which animal? Alpha male, other male, or female?|date=June 2021}} during ] associated with the behavior of alpha male wolves preventing other males from mounting females in heat.<ref>{{cite journal | doi = 10.1002/zoo.1430050103 | title = Wolf scent marking with raised-leg urination | journal = Zoo Biology | volume = 5 | pages = 7–20 | year = 1986 | last1 = Mertl-Millhollen | first1 = Anne S. | last2 = Goodmann | first2 = Patricia A. | last3 = Klinghammer | first3 = Erich }}</ref><ref>{{cite book | title = Handbook of Applied Dog Behavior and Training, Adaptation and Learning | author = Steven R. Lindsay | publisher = John Wiley and Sons | date = 2013 }}</ref>
	Methylparaben is commonly used as a fungicide in '']'' food media. Usage of methylparaben is known to slow ''Drosophila'' growth rate in the larval and pupal stages.
	==Safety==		== Uses ==
		⚫	Methylparaben is an anti-fungal agent often used in a variety of cosmetics and personal-care products. It is also used as a food preservative and has the ] E218.
⚫	Methylparaben is produced naturally and found in several fruits, primarily blueberries, along with other parabens. There is no evidence that methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.<ref></ref> Methyl and propylparabens are considered GRAS (generally regarded as safe) for food and cosmetic antibacterial preservation.<ref>, ]</ref> Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.
			Methylparaben is commonly used as a ] in '']'' food media at 0.1%.<ref>{{Cite web|url=https://bdsc.indiana.edu/information/recipes/germanfood.html|title=Bloomington Drosophila Stock Center}}</ref> To ''Drosophila'', methylparaben is ] at higher concentrations, has an ]ic effect (mimicking estrogen in rats and having anti-] activity), and slows the growth rate in the larval and pupal stages at 0.2%.<ref>{{Cite journal | title = Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster | vauthors = Gu W, Xie DJ, Hour XW | journal = Food Science | year = 2009 | volume = 30 | issue = 1 | pages = 252–254 | url = http://www.spkx.net.cn/EN/Y2009/V30/I1/252 }}</ref>
⚫	Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.<ref name="Soni">{{cite journal |author=Soni MG, Taylor SL, Greenberg NA, Burdock GA |title=Evaluation of the health aspects of methyl paraben: a review of the published literature |journal=Food Chem. Toxicol. |volume=40 |issue=10 |pages=1335–73 |year=2002 |month=October |pmid=12387298 |doi= 10.1016/S0278-6915(02)00107-2|url=http://linkinghub.elsevier.com/retrieve/pii/S0278691502001072}}</ref> It is ] to ] and rapidly excreted without accumulation in the body.<ref name="Soni"/> Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and ] administration.<ref name="Soni"/> In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.<ref name="Soni"/>
			== Safety ==
⚫	Studies indicate that methylparaben applied on the skin may react with ] leading to increased skin aging and DNA damage.<ref>{{cite journal | last1 = Handa | first1 = O | last2 = Kokura | first2 = S | last3 = Adachi | first3 = S | last4 = Takagi | first4 = T | last5 = Naito | first5 = Y | last6 = Tanigawa | first6 = T | last7 = Yoshida | first7 = N | last8 = Yoshikawa | first8 = T | title = Methylparaben potentiates UV-induced damage of skin keratinocytes. | journal = Toxicology | volume = 227 | issue = 1-2 | pages = 62–72 | year = 2006 | pmid = 16938376 | doi = 10.1016/j.tox.2006.07.018}}</ref><ref>{{cite journal | last1 = Okamoto | first1 = Yoshinori | last2 = Hayashi | first2 = Tomohiro | last3 = Matsunami | first3 = Shinpei | last4 = Ueda | first4 = Koji | last5 = Kojima | first5 = Nakao | title = Combined Activation of Methyl Paraben by Light Irradiation and Esterase Metabolism toward Oxidative DNA Damage | journal = Chemical Research in Toxicology | volume = 21 | issue = 8 | pages = 1594–9 | year = 2008 | pmid = 18656963 | doi = 10.1021/tx800066u}}</ref>
		⚫	There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics. Methylparaben and ] are considered ] (GRAS) by the ] for food and cosmetic antibacterial preservation.<ref>{{cite web | url = https://www.fda.gov/cosmetics/productsingredients/ingredients/ucm128042.htm | title = Parabens | date = 9 September 2020 | publisher = ] }}</ref> Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.
		⚫	Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.<ref name="Soni">{{cite journal | vauthors = Soni MG, Taylor SL, Greenberg NA, Burdock GA | title = Evaluation of the health aspects of methyl paraben: a review of the published literature | journal = Food and Chemical Toxicology | volume = 40 | issue = 10 | pages = 1335–73 | date = October 2002 | pmid = 12387298 | doi = 10.1016/S0278-6915(02)00107-2 }}</ref> It is ] to ] and rapidly excreted in urine without accumulating in the body.<ref name="Soni"/> Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and ] administration in animals.<ref name="Soni"/> In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.<ref name="Soni"/> A 2008 study found no competitive binding for human estrogen and androgen receptors for methylparaben, but varying levels of competitive binding were seen with butyl- and isobutyl-paraben.<ref>{{cite journal | vauthors = Alan AF | title = Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products | journal = International Journal of Toxicology | volume = 27 Suppl 4 | issue = Suppl 4 | pages = 1–82 | date = 2008 | pmid = 19101832 | doi = 10.1080/10915810802548359 }}</ref>
⚫	==References==
		⚫	Studies indicate that methylparaben applied on the skin may react with ], leading to increased skin aging and DNA damage.<ref>{{cite journal | vauthors = Handa O, Kokura S, Adachi S, Takagi T, Naito Y, Tanigawa T, Yoshida N, Yoshikawa T | display-authors = 6 | title = Methylparaben potentiates UV-induced damage of skin keratinocytes | journal = Toxicology | volume = 227 | issue = 1–2 | pages = 62–72 | date = October 2006 | pmid = 16938376 | doi = 10.1016/j.tox.2006.07.018 | bibcode = 2006Toxgy.227...62H }}</ref><ref>{{cite journal | vauthors = Okamoto Y, Hayashi T, Matsunami S, Ueda K, Kojima N | title = Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage | journal = Chemical Research in Toxicology | volume = 21 | issue = 8 | pages = 1594–9 | date = August 2008 | pmid = 18656963 | doi = 10.1021/tx800066u }}</ref>
		⚫	== References ==
	{{reflist}}		{{reflist}}
	==External links==		== External links ==
	* at Hazardous Substances Data Bank		* at Hazardous Substances Data Bank
	* at Household Products Database		* {{Webarchive|url=https://web.archive.org/web/20170501133733/https://hpd.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=2065 |date=2017-05-01 }} at Household Products Database
			* European Commission Scientific Committee on Consumer Products Extended Opinion on the Safety Evaluation of Parabens (2005)
			{{Phenolic acid}}
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