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Revision as of 14:44, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 449140127 of page Propylparaben for the Chem/Drugbox validation project (updated: '').		Latest revision as of 15:06, 9 December 2024 edit Citation bot (talk | contribs)Bots5,429,007 edits Altered title. Add: newspaper, work, bibcode, pmid, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 17/2664
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			{{short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 412738324
	| ImageFile_Ref = {{chemboximage|correct|??}}		| verifiedrevid = 464217729
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile=Propylparaben.svg		| ImageFile = Propylparaben.svg
	|ImageSize=		| ImageSize =
			| ImageFile1 = Propylparaben ball-and-stick.png
⚫	|IUPACName=propyl 4-hydroxybenzoate
			| ImageSize1 =
	|OtherNames=4-Hydroxybenzoesäurepropylester;<br>propyl paraben;<br>propyl ''p''-hydroxybenzoate;<br>propyl parahydroxybenzoate;<br>nipasol;<br>E216
		⚫	| PIN = Propyl 4-hydroxybenzoate
⚫	|Section1= {{Chembox Identifiers
			| OtherNames = {{ubl
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| Propyl paraben
			| Propyl ''p''-hydroxybenzoate
			| Propyl parahydroxybenzoate
			| Nipasol
			| E216
			}}
		⚫	| Section1 = {{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 6907		| ChemSpiderID = 6907
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
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	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 194014		| ChEMBL = 194014
			| ChEBI = 32063
			| EINECS = 202-307-7
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3		| StdInChI = 1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = QELSKZZBTMNZEB-UHFFFAOYSA-N		| StdInChIKey = QELSKZZBTMNZEB-UHFFFAOYSA-N
	| CASNo=94-13-3		| CASNo =94-13-3
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem=7175		| PubChem =7175
	| SMILES = O=C(OCCC)c1ccc(O)cc1		| SMILES = O=C(OCCC)c1ccc(O)cc1
	}}		}}
	|Section2= {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=10 | H=12 | O=3
	| Formula=C<sub>10</sub>H<sub>12</sub>O<sub>3</sub>
			| Appearance =
	| MolarMass=180.2 g/mol
			| Density = 1.0630{{nbsp}}g/cm<sup>3</sup>
	| Appearance=
			| MeltingPtC = 96 to 99
	| Density= 1.0630 g/cm^3
			| MeltingPt_notes =
	| MeltingPt= 96-99 °C
	| BoilingPt=		| BoilingPt =
	| Solubility=		| Solubility =
	}}		}}
	|Section3= {{Chembox Hazards		| Section3 = {{Chembox Hazards
	| MainHazards=		| MainHazards =
	| FlashPt=		| FlashPt =
			| AutoignitionPt =
	| Autoignition=
			| NFPA-H = 2
			| NFPA-F = 1
			| NFPA-R = 0
	}}		}}
	| Section8 = {{Chembox Related		| Section8 = {{Chembox Related
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	| OtherFunctn =		| OtherFunction =
			| OtherFunction_label =
	| Function =
	| OtherCpds = ]<br />]<br />]<br />]		| OtherCompounds = ]<br />]<br />]<br />]<br />]
	}}		}}
	}}		}}
			'''Propylparaben''' (also spelled '''propyl paraben''') is the ''n''-propyl ] of ]. It occurs as a ] ] found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods.<ref name="Oishi-2002">{{cite journal|last=Oishi|title=Effects of propyl paraben on the male reproductive system |journal=Food and Chemical Toxicology |date=December 2002 |pmid=12419695 |volume=40 |issue=12 |pages=1807–1013 |doi=10.1016/s0278-6915(02)00204-1}}</ref> It is a member of the class of ]s and can be used as a ] in many water-based cosmetics, such as creams, lotions, shampoos, and bath products.<ref>{{Cite web |last=PubChem |title=Propylparaben |url=https://pubchem.ncbi.nlm.nih.gov/compound/7175 |access-date=2021-12-01 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> As a ], it has an ], which is E216.
			'''Sodium propyl ''p''-hydroxybenzoate''', the ] ] of propylparaben, a compound with formula Na(C<sub>3</sub>H<sub>7</sub>(C<sub>6</sub>H<sub>4</sub>COO)O), is used similarly as a food additive and as an anti-fungal preservation agent. Its E number is E217.
			In 2010, the European Union Scientific Committee on Consumer Safety stated that the use of butylparaben and propylparaben as preservatives in finished cosmetic products as safe to the consumer, as long as the sum of their concentrations does not exceed 0.19%.<ref>{{Cite web|url=http://ec.europa.eu/health/scientific_committees/consumer_safety/docs/sccs_o_041.pdf|title=Scientific Committee on Consumer Safety Opinion on Parabens COLIPA n° P82|last=Directorate-General for Consumer Safety|first=European Union|date=2011|access-date=December 15, 2017}}</ref>
			== Applications ==
			===Food===
			Under FDA regulations, propylparaben is safe to use with a maximum of 0.1% of the weight of the finished food or 200–450 ppm for a variety of foods like ], ]s, jams, baked goods, and ]s.<ref name="Soni-2001">{{Cite journal |last1=Soni |first1=M. G. |last2=Burdock |first2=G. A. |last3=Taylor |first3=S. L. |last4=Greenberg |first4=N. A. |date=June 2001 |title=Safety assessment of propyl paraben: a review of the published literature |journal=Food and Chemical Toxicology |volume=39 |issue=6 |pages=513–532 |doi=10.1016/S0278-6915(00)00162-9 |pmid=11346481 |issn=0278-6915}}</ref> It is even found naturally in a plant called ''Stocksia brahuica''.<ref name="Soni-2005">{{Cite journal |last1=Soni |first1=M.G. |last2=Carabin |first2=I.G. |last3=Burdock |first3=G.A. |date=July 2005 |title=Safety assessment of esters of p-hydroxybenzoic acid (parabens) |journal=Food and Chemical Toxicology |language=en |volume=43 |issue=7 |pages=985–1015 |doi=10.1016/j.fct.2005.01.020|pmid=15833376 }}</ref> It is often used as a food and cosmetic preservative as it has no odor or taste, and does not change the texture.<ref name="Soni-2001"/> The compound has some medicinal application as well as it has been used in ], ]s, eyewashes, weight gain drinks, and recently has been discovered to have ] activities suggesting it may be useful in the development of anticonvulsant medicine.<ref name="Soni-2001"/><ref name="Talevi 527–538">{{Cite journal |last1=Talevi |first1=Alan |last2=Bellera |first2=Carolina L. |last3=Castro |first3=Eduardo A. |last4=Bruno-Blanch |first4=Luis E. |date=2007-10-25 |title=A successful virtual screening application: prediction of anticonvulsant activity in MES test of widely used pharmaceutical and food preservatives methylparaben and propylparaben |journal=Journal of Computer-Aided Molecular Design |language=en |volume=21 |issue=9 |pages=527–538 |doi=10.1007/s10822-007-9136-9 |pmid=17960329 |bibcode=2007JCAMD..21..527T |issn=0920-654X}}</ref>
			Recently, a study of combining plasma-activated water (PAW) with propylparaben show increased ] efficacy of PAW for fresh produce sanitation. PAW is used for fresh produce sanitation. However, when used in food applications, its effectiveness decreased because of interfering substances like ]s, ]s, and ]s. With propylparaben and PAW, bacteria undergo more oxidative stress and cell damage, increasing preservation of produce. For now, the potential health risk and residue level of propylparaben with this new method is still unknown.
			Propylparaben is also used as a ], and is designated with the ] E216. Propylparaben is commonly used as a preservative in packaged baked goods, particularly pastries and tortillas.<ref name="NJTimesMay2023">{{cite news |author=Dana G. Smith |date=April 13, 2023 |title=Two States Have Proposed Bans on Common Food Additives Linked to Health Concerns |work=New York Times |url=https://www.nytimes.com/2023/04/13/well/eat/food-additive-ban.html |access-date=May 23, 2023}}</ref> Propylparaben is also a Standardized Chemical Allergen and is used in allergenic testing.<ref>{{Cite web |title=DailyMed - Browse Drug Classes |url=https://dailymed.nlm.nih.gov/dailymed/browse-drug-classes.cfm |access-date=2021-12-01 |website=dailymed.nlm.nih.gov}}</ref><ref>{{Cite web |title=Propylparaben |url=https://go.drugbank.com/drugs/DB14177 |access-date=2021-12-01 |website=go.drugbank.com}}</ref>
			===Cosmetic===
			Propylparaben is one of the most commonly used paraben in cosmetic formulation.<ref name="Soni-2001"/> It can be found in ]s, ], ], ], shaving products, and many more.<ref name="Center for Food Safety and Applied Nutrition-2022">{{Cite web |author=Center for Food Safety and Applied Nutrition |date=2022-03-03 |title=Parabens in Cosmetics |url=https://www.fda.gov/cosmetics/cosmetic-ingredients/parabens-cosmetics |publisher=FDA |language=en}}</ref> In cosmetic products, propylparaben is typically combined with other parabens (such as methylparaben) or other ]s to protect against a broader range of microorganisms.<ref name="Soni-2001"/> The chemical stability in room temperature and wide pH range (4.5–7.5) is advantageous to prolong a product shelf life. Under ] regulations, the maximum use of concentration for propylparaben is 25%.<ref name="Center for Food Safety and Applied Nutrition-2022" /> However, cosmetics do not require testing by the FDA prior to sale.<ref name="Center for Food Safety and Applied Nutrition-2022" /> While there is no conclusive evidence of harm to human health from propylparaben, more cosmetic companies are creating paraben-free lines, specifically in shampoos. Since parabens can easily absorb through skin, daily use is believed to cause toxic accumulation in the body that might be harmful. Some people may also experience allergic reaction to parabens including redness, irritation, itchiness, flaking, and hives.<ref>{{Cite web |last=Jones |first=Oliver A. H. |date=2023-03-27 |title=What is a paraben and why are so many products advertised as 'paraben-free'? |url=http://theconversation.com/what-is-a-paraben-and-why-are-so-many-products-advertised-as-paraben-free-198994 |access-date=2023-11-10 |website=The Conversation |language=en-US}}</ref>
			===Pharmaceutical===
			Used since the mid-1920s as a preservative, parabens are present in ]es, pills, ], injectable solutions, ], and even weight-gain drinks.<ref name="Soni-2001"/> Unlike cosmetics where propylparaben is mostly used in the surface, propylparaben is ingested and absorbed. According to a law from the ] (European Economic Community), the maximum level of parabens in pharmaceutical products is 1% (w/w),<ref>{{Cite web |title=EUR-Lex - l21191 - EN - EUR-Lex |url=https://eur-lex.europa.eu/EN/legal-content/summary/cosmetic-products-until-2013.html |access-date=2023-11-10 |website=eur-lex.europa.eu |language=en}}</ref> much stricter and defined than cosmetics. Propylparaben also cannot be used alone in ] products, such as eyewash because it may cause irritation at the effective concentration level to have antimicrobial activities.<ref name="Soni-2001"/>
			A MES (Maximal Electroshock) test also shows anticonvulsant activity in propylparaben. Since propylparaben has minimum to no toxicity and well absorbed in the GI tract, it can potentially be develop to new anticonvulsant medicine to control seizures.<ref name="Talevi 527–538"/>
			== Chemical properties ==
			Propylparaben is a stable and non-volatile compound with ] properties and has been used as ]s in food for over 50 years.<ref name="Soni-2001"/> It is typically used in a variety of water-based cosmetics and personal-care products.<ref>{{Cite web |title=propylparaben (CHEBI:32063) |url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:32063 |access-date=2021-12-01 |website=www.ebi.ac.uk}}</ref> it is a white ] solid with a molecular weight of 202.18 ].<ref name="Moscoso-Ramírez-2014">{{Cite journal |last1=Moscoso-Ramírez |first1=Pedro A. |last2=Montesinos-Herrero |first2=Clara |last3=Palou |first3=Lluís |date=September 2014 |title=Antifungal activity of sodium propylparaben alone or in combination with low doses of imazalil against Penicillium decay on citrus fruit |journal=European Journal of Plant Pathology |language=en |volume=140 |issue=1 |pages=145–157 |doi=10.1007/s10658-014-0450-5 |bibcode=2014EJPP..140..145M |issn=0929-1873}}</ref> Humans most often absorb the chemical through their skin or ingestion as it is in many cosmetic and food products as an ] preservative.<ref name="Shin-2019">{{Cite journal |last1=Shin |first1=Mi-Yeon |last2=Shin |first2=Chorong |last3=Choi |first3=Jeong Weon |last4=Lee |first4=Jangwoo |last5=Lee |first5=Seungho |last6=Kim |first6=Sungkyoon |date=September 2019 |title=Pharmacokinetic profile of propyl paraben in humans after oral administration |journal=Environment International |volume=130 |at=104917 |doi=10.1016/j.envint.2019.104917 |issn=0160-4120|doi-access=free |pmid=31234001 |bibcode=2019EnInt.13004917S }}</ref><ref name="Moscoso-Ramírez-2014" /> It is ] in two major pathways leading to the production of either conjugated metabolites or hydrolysates (PHBA, PHHA).<ref name="Shin-2019" /> These products are excreted from the body in urine.<ref name="Shin-2019" /> Propylparaben is an effective ], especially against green and ]s on ].<ref name="Moscoso-Ramírez-2014" /> Its high ] in water allows it to be applied to the fruits easily.<ref name="Moscoso-Ramírez-2014" />
			== Synthesis ==
			One of the simplest ways to produce propylparaben is through the ] of ] with ] using an acidic ].<ref>{{Cite journal |last1=Hazarika |first1=Mridul |last2=Parajuli |first2=Raghab |last3=Phukan |first3=Prodeep |date=January 2007 |title=Synthesis of parabens using montmorillonite K10 clay as catalyst: A green protocol |url=https://nopr.niscpr.res.in/bitstream/123456789/1070/1/IJCT%2014(1)%20(2007)%20104-106.pdf |journal=Indian Journal of Chemical Technology |volume=14 |pages=104–106}}</ref> The first major step includes the ] of the ] due to the acidic conditions. This ] results in a positive charge on the ] which will offset the ] from the ] ] atom, this allows the ] to preform a ] attack on the ].<ref name="Chemistry LibreTexts-2015">{{Cite web |date=2015-08-26 |title=21.6: Chemistry of Esters |url=https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Organic_Chemistry_(Morsch_et_al.)/21%3A_Carboxylic_Acid_Derivatives-_Nucleophilic_Acyl_Substitution_Reactions/21.06%3A_Chemistry_of_Esters |access-date=2023-11-26 |website=Chemistry LibreTexts |language=en}}</ref> The proton of the nucleophilic propanol is then transferred by the ] to the ]s ]. The ] can then act as a good ] and be expelled from the ] as ], allowing the ] ] to reform. Finally, ] of the reformed ] will produce the final ] product, propylparaben.<ref name="Chemistry LibreTexts-2015" />
			]
			== Safety ==
			Propylparaben, among other parabens, has been raising concerns on its possible interaction and disruption of ] in the ]<ref name="Boberg-2010">{{Cite journal |last1=Boberg |first1=Julie |last2=Taxvig |first2=Camilla |last3=Christiansen |first3=Sofie |last4=Hass |first4=Ulla |date=September 2010 |title=Possible endocrine disrupting effects of parabens and their metabolites |journal=Reproductive Toxicology |language=en |volume=30 |issue=2 |pages=301–312 |doi=10.1016/j.reprotox.2010.03.011|pmid=20381602 |bibcode=2010RepTx..30..301B }}</ref> Exposure to high levels of propylparaben has been correlated to lower ] and ] production in males in animal studies,<ref name="Oishi-2002"/><ref name="Boberg-2010" /> with one other study showing that it can even act as an effective ].<ref>{{Cite journal |last1=Bao-Liang |first1=Song |last2=Hai-Ying |first2=Li |last3=Dun-Ren |first3=Peng |date=March 1989 |title=In vitro spermicidal activity of parabens against human spermatozoa |url=https://linkinghub.elsevier.com/retrieve/pii/0010782489900656 |journal=Contraception |language=en |volume=39 |issue=3 |pages=331–335 |doi=10.1016/0010-7824(89)90065-6|pmid=2714092 }}</ref> Animal studies of propylparaben in the body show that propylparaben is metabolized from the ] and excreted rapidly through urine with no accumulation in the body. Despite parabens' interaction with the ], it has not been shown to be significantly correlated with ].<ref name="Boberg-2010" /> With cracked or damaged skins, the use of propylparaben in cosmetics or skincare can result in ]; however, for normal skin, it is considered safe.<ref name="Soni-2005"/>
			As of May 2023, ] began considering banning the use of propylparaben because studies in humans and animals indicate that it acts as an endocrine disruptor and affects reproductive health.<ref name="Oishi-2002" /><ref name="NJTimesMay2023" />
			In October 2023, the ] signed a bill into law outlawing the use of propylparaben in foods by 2027.<ref>{{cite web |title=AB-418 The California Food Safety Act. |url=https://leginfo.legislature.ca.gov/faces/billCompareClient.xhtml?bill_id=202320240AB418&showamends=false |publisher=] |language=en}}</ref><ref>{{Cite web |last=Chuck |first=Elizabeth |date=2023-09-12 |title=California Legislature passes first bill in U.S. to ban food additives, including red dye No. 3 |url=https://www.nbcnews.com/news/us-news/california-legislature-passes-first-bill-us-banning-food-additives-red-rcna104644 |access-date=2023-09-14 |website=www.nbcnews.com |language=en}}</ref> The new law bans the manufacture, sale, and distribution of propylparaben and three other additives (], ], and ]). This is the first law in the U.S. to ban it and will possibly have nationwide effects.<ref>{{cite news |url=https://www.washingtonpost.com/wellness/2023/10/11/california-skittles-ban-chemicals-food/ |title=California isn't banning Skittles, but four additives will be removed |first=Marlene |last=Cimons |newspaper=Washington Post |date=Oct 11, 2023 |url-access=subscription}} The article notes that Red dye No. 3, bromated vegetable oil, potassium bromate and propyl paraben all have been linked to risk of cancer and hyperactivity in children.</ref>
			== References ==
			{{Reflist}}
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