Methylparaben

Methylparaben
source ↗	source ↗
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 Y;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31835 N;
ChEMBL	ChEMBL325372 Y;
ChemSpider	7176 Y;
ECHA InfoCard	100.002.532
E number	E218 (preservatives)
IUPHAR/BPS	6273;
KEGG	D01400 Y;
PubChem CID	7456;
UNII	A2I8C7HI9T Y;
CompTox Dashboard (EPA)	DTXSID4022529 ;
	InChI InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Y Key: LXCFILQKKLGQFO-UHFFFAOYSA-N Y; 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
Density	1.383 g/cm3
Melting point	131 °C (268 °F; 404 K)
Boiling point	265 °C (509 °F; 538 K)
UV-vis (λmax)	255 nm (methanol)
Magnetic susceptibility (χ)	−88.7·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)	source ↗ 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). N verify (what is YN ?) Infobox references

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH₃O₂CC₆H₄OH. It is the methyl ester of p-hydroxybenzoic acid. Several related esters are known (ethyl-, propyl-, butylparaben). Together they are the most common preservatives in cosmetics and foods. Among their advantages, parabens are inexpensive, colorless, stable, odorless, and readily biodegraded.²

Natural occurrences

Methylparaben serves as a pheromone for a variety of insects³ and is a component of queen mandibular pheromone.

It is a pheromone in wolves produced during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat.⁴⁵

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%.⁶ 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%.⁷

Safety

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

Some controversy exists about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.¹⁰ Methylparaben and propylparaben are considered generally recognized as safe (GRAS) by the USFDA for food and cosmetic antibacterial preservation.¹¹ 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

Methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage.¹²¹³

References

"Methylparaben Experimental Properties". PubChem.
Matwiejczuk, Natalia; Galicka, Anna; Brzóska, Małgorzata M. (2020). "Review of the safety of application of cosmetic products containing parabens". Journal of Applied Toxicology. 40 (1): 176–210. doi:10.1002/jat.3917. PMID 31903662.
"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.
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.
Haman, Camille; Dauchy, Xavier; Rosin, Christophe; Munoz, Jean-François (2015). "Occurrence, fate and behavior of parabens in aquatic environments: A review". Water Research. 68: 1–11. Bibcode:2015WatRe..68....1H. doi:10.1016/j.watres.2014.09.030. PMID 25462712.
"Parabens". Food and Drug Administration. 9 September 2020. Archived from the original on March 30, 2014.
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] Matwiejczuk, Natalia; Galicka, Anna; Brzóska, Małgorzata M. (2020). "Review of the safety of application of cosmetic products containing parabens". Journal of Applied Toxicology. 40 (1): 176–210. doi:10.1002/jat.3917. PMID 31903662.

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

[4] 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.

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

[6] "Bloomington Drosophila Stock Center".

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

[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] Haman, Camille; Dauchy, Xavier; Rosin, Christophe; Munoz, Jean-François (2015). "Occurrence, fate and behavior of parabens in aquatic environments: A review". Water Research. 68: 1–11. Bibcode:2015WatRe..68....1H. doi:10.1016/j.watres.2014.09.030. PMID 25462712.

[11] "Parabens". Food and Drug Administration. 9 September 2020. Archived from the original on March 30, 2014.

[12] 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.

[13] 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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