Methylparaben: Difference between revisions

Methylparaben
Names
	Preferred IUPAC name Methyl 4-hydroxybenzoate
	Other names Methyl paraben; Methyl p-hydroxybenzoate; Methyl parahydroxybenzoate; Nipagin M; E number E218; Tegosept; Mycocten;
Identifiers
CAS Number	99-76-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31835 ;
ChEMBL	ChEMBL325372 ;
ChemSpider	7176 ;
ECHA InfoCard	100.002.532
E number	E218 (preservatives)
IUPHAR/BPS	6273;
KEGG	D01400 ;
PubChem CID	7456;
UNII	A2I8C7HI9T ;
CompTox Dashboard (EPA)	DTXSID4022529 ;
	InChI InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Key: LXCFILQKKLGQFO-UHFFFAOYSA-N ; InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Key: LXCFILQKKLGQFO-UHFFFAOYAH;
	SMILES COC(=O)c1ccc(O)cc1;
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	Colorless crystals or white crystalline powder
UV-vis (λmax)	255 nm (methanol)
Magnetic susceptibility (χ)	−88.7·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)	1 1 0
Related compounds
Related Parabens	Ethylparaben; Propylparaben; Butylparaben
Related compounds	Methyl salicylate (ortho isomer)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH₃(C₆H₄(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

Natural occurrences

Methylparaben serves as a pheromone for a variety of insects^[2] and is a component of queen mandibular pheromone.

It is a pheromone in wolves produced^{[clarification needed]} during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat.^[3]^[4]

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 E number E218.

Methylparaben is commonly used as a fungicide in Drosophila food media at 0.1%.^[5] To Drosophila, methylparaben is toxic at higher concentrations, has an estrogenic effect (mimicking estrogen in rats and having anti-androgenic activity), and slows the growth rate in the larval and pupal stages at 0.2%.^[6]

Safety

There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics. Methylparaben and propylparaben are considered generally recognized as safe (GRAS) by the USFDA for food and cosmetic antibacterial preservation.^[7] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.^[8] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body.^[8] Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and parenteral administration in animals.^[8] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.^[8] 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.^[9]

Studies indicate that methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage.^[10]^[11]

References

^ "Methylparaben Experimental Properties". PubChem.
^ "Semiochemical - me-4-hydroxybenzoate". pherobase.com.
^ Mertl-Millhollen, Anne S.; Goodmann, Patricia A.; Klinghammer, Erich (1986). "Wolf scent marking with raised-leg urination". Zoo Biology. 5: 7–20. doi:10.1002/zoo.1430050103.
^ Steven R. Lindsay (2013). Handbook of Applied Dog Behavior and Training, Adaptation and Learning. John Wiley and Sons.
^ "Bloomington Drosophila Stock Center".
^ Gu W, Xie DJ, Hour XW (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.
^ "Parabens". Food and Drug Administration. 9 September 2020.
^ ^a ^b ^c ^d Soni MG, Taylor SL, Greenberg NA, Burdock GA (October 2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298.
^ Alan AF (2008). "Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products". International Journal of Toxicology. 27 Suppl 4 (Suppl 4): 1–82. doi:10.1080/10915810802548359. PMID 19101832.
^ Handa O, Kokura S, Adachi S, Takagi T, Naito Y, Tanigawa T, et al. (October 2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology. 227 (1–2): 62–72. Bibcode:2006Toxgy.227...62H. doi:10.1016/j.tox.2006.07.018. PMID 16938376.
^ Okamoto Y, Hayashi T, Matsunami S, Ueda K, Kojima N (August 2008). "Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage". Chemical Research in Toxicology. 21 (8): 1594–9. doi:10.1021/tx800066u. PMID 18656963.

External links

Methylparaben at Hazardous Substances Data Bank
Methylparaben Archived 2017-05-01 at the Wayback Machine at Household Products Database
European Commission Scientific Committee on Consumer Products Extended Opinion on the Safety Evaluation of Parabens (2005) [1]

[1] "Methylparaben Experimental Properties". PubChem.

[2] "Semiochemical - me-4-hydroxybenzoate". pherobase.com.

[3] Mertl-Millhollen, Anne S.; Goodmann, Patricia A.; Klinghammer, Erich (1986). "Wolf scent marking with raised-leg urination". Zoo Biology. 5: 7–20. doi:10.1002/zoo.1430050103.

[4] Steven R. Lindsay (2013). Handbook of Applied Dog Behavior and Training, Adaptation and Learning. John Wiley and Sons.

[5] "Bloomington Drosophila Stock Center".

[6] Gu W, Xie DJ, Hour XW (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.

[7] "Parabens". Food and Drug Administration. 9 September 2020.

[Soni-8] Soni MG, Taylor SL, Greenberg NA, Burdock GA (October 2002). "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298.

[9] Alan AF (2008). "Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products". International Journal of Toxicology. 27 Suppl 4 (Suppl 4): 1–82. doi:10.1080/10915810802548359. PMID 19101832.

[10] Handa O, Kokura S, Adachi S, Takagi T, Naito Y, Tanigawa T, et al. (October 2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology. 227 (1–2): 62–72. Bibcode:2006Toxgy.227...62H. doi:10.1016/j.tox.2006.07.018. PMID 16938376.

[11] Okamoto Y, Hayashi T, Matsunami S, Ueda K, Kojima N (August 2008). "Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage". Chemical Research in Toxicology. 21 (8): 1594–9. doi:10.1021/tx800066u. PMID 18656963.

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@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
 {{chembox
 | Verifiedfields = changed
@@ Line 8: / Line 9: @@
 | ImageFileR1 = Methylparaben.png
 | ImageSizeR1 = 100px
-| IUPACName = Methyl 4-hydroxybenzoate
+| PIN = Methyl 4-hydroxybenzoate
-| OtherNames = Methyl paraben;<br />Methyl ''p''-hydroxybenzoate;<br />Methyl parahydroxybenzoate;<br />Nipagin M;<br />[[E number]] E218; Tegosept; Mycocten
+| OtherNames = {{Unbulleted list|Methyl paraben|Methyl ''p''-hydroxybenzoate|Methyl parahydroxybenzoate|Nipagin M|[[E number]] E218|Tegosept|Mycocten}}
 |Section1={{Chembox Identifiers
 | IUPHAR_ligand = 6273
@@ Line 31: / Line 32: @@
 | CASNo = 99-76-3
 | PubChem = 7456
-| SMILES = COC(=O)c1ccc(cc1)O
+| SMILES = COC(=O)c1ccc(O)cc1
 }}
 |Section2={{Chembox Properties
 | C=8 | H=8 | O=3
-| Appearance = Colorless crystals or white crystalline powder <ref>https://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties</ref>
+| 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>
 | Density =
-| LambdaMax = 255 nm (methanol)
+| LambdaMax = 255{{nbsp}}nm (methanol)
 | MeltingPt =
 | BoilingPt =
 | Solubility =
-| MagSus = -88.7·10<sup>−6</sup> cm<sup>3</sup>/mol
+| MagSus = −88.7·10<sup>−6</sup>{{nbsp}}cm<sup>3</sup>/mol
   }}
 |Section3={{Chembox Hazards
@@ Line 60: / Line 61: @@
 }}
 [[File:Methylparaben UV-vis spectrum.png|thumb|right|UV-visible spectrum of methylparaben]]
-'''Methylparaben''', also '''methyl paraben''', one of the [[parabens]], is a preservative with the chemical formula CH<sub>3</sub>(C<sub>6</sub>H<sub>4</sub>(OH)COO). It is the [[methyl]] [[ester]] of [[P-Hydroxybenzoic acid|''p''-hydroxybenzoic acid]].
+'''Methylparaben''' ('''methyl paraben''') one of the [[parabens]], is a preservative with the chemical formula CH<sub>3</sub>(C<sub>6</sub>H<sub>4</sub>(OH)COO). It is the [[methyl]] [[ester]] of [[P-Hydroxybenzoic acid|''p''-hydroxybenzoic acid]].
 == Natural occurrences ==
-Methylparaben serves as a [[pheromone]] for a variety of insects<ref>[http://www.pherobase.com/database/compound/compounds-detail-me-4-hydroxybenzoate.php Semiochemical - me-4-hydroxybenzoate], pherobase.com</ref> and is a component of [[queen mandibular pheromone]].
+Methylparaben serves as a [[pheromone]] 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 [[queen mandibular pheromone]].
-Some plants produce methylparaben, example [[thale cress]].<ref>{{cite journal |vauthors=Walker TS, Bais HP, Halligan KM, Stermitz FR, Vivanco JM |title=Metabolic profiling of root exudates of Arabidopsis thaliana |journal=Journal of Agricultural and Food Chemistry |volume=51 |issue=9 |pages=2548–54 |year=2003 |pmid=12696935 |doi=10.1021/jf021166h }}</ref> It is commonly used in the preparation of liquid dosage forms.
+It is a pheromone in wolves produced{{clarify|reason=produced by which animal? Alpha male, other male, or female?|date=June 2021}} during [[estrus]] 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>
 == 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 [[E number]] E218.
-Methylparaben is commonly used as a [[fungicide]] in ''[[Drosophila]]'' food media. To ''Drosophila'', methylparaben is [[toxicity|toxic]] at higher concentrations, has an [[estrogen]]ic effect, and slows the growth rate in the larval and pupal stages at lower concentrations.<ref>{{Cite journal | title = Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster | author = Gu Wei | 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 commonly used as a [[fungicide]] in ''[[Drosophila]]'' 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 [[toxicity|toxic]] at higher concentrations, has an [[estrogen]]ic effect (mimicking estrogen in rats and having anti-[[Androgen|androgenic]] 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 has a known use in the synthesis of [[Nifuroxazide]].
-When methylparaben is reacted with [[Araldite M]], the product is [[Terbufibrol]].
 == Safety ==
-There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.  Methylparaben and [[propylparaben]] are considered [[generally recognized as safe]] (GRAS) for food and cosmetic antibacterial preservation.<ref>[http://www.fda.gov/cosmetics/productsingredients/ingredients/ucm128042.htm Parabens], [[Food and Drug Administration]]</ref>  Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.
+There is controversy about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.  Methylparaben and [[propylparaben]] are considered [[generally recognized as safe]] (GRAS) by the [[USFDA]] 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 = [[Food and Drug Administration]] }}</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 |year=2002 |pmid=12387298 |doi=10.1016/S0278-6915(02)00107-2 }}</ref> It is [[hydrolysis|hydrolyzed]] to [[4-Hydroxybenzoic acid|''p''-hydroxybenzoic acid]] 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 [[parenteral]] 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"/>
+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 [[hydrolysis|hydrolyzed]] to [[4-Hydroxybenzoic acid|''p''-hydroxybenzoic acid]] 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 [[parenteral]] 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>
-Studies indicate that methylparaben applied on the skin may react with [[Ultraviolet|UVB]], 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 (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>
+Studies indicate that methylparaben applied on the skin may react with [[Ultraviolet|UVB]], 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 ==
@@ Line 87: / Line 86: @@
 == External links ==
 * [http://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?dbs+hsdb:@term+@rn+99-76-3 Methylparaben] at Hazardous Substances Data Bank
-* [http://hpd.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=2065 Methylparaben] at Household Products Database
+* [http://hpd.nlm.nih.gov/cgi-bin/household/brands?tbl=chem&id=2065 Methylparaben] {{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) [http://ec.europa.eu/health/ph_risk/committees/04_sccp/docs/sccp_o_019.pdf]
 {{Phenolic acid}}
-[[Category:Phenolic acids]]
-[[Category:Carboxylate esters]]
 [[Category:Methyl esters]]
-[[Category:Fungicides]]
+[[Category:Parabens]]
+[[Category:E-number additives]]
+[[Category:Semiochemicals]]
+[[Category:Insect pheromones]]
 [[ja:メチルパラベン]]