Methylparaben
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| Preferred IUPAC name
Methyl 4-hydroxybenzoate | |||
| Other names
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3D model (JSmol)
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| Properties | |||
| C8H8O3 | |||
| Molar mass | 152.149 g·mol−1 | ||
| Appearance | Colorless crystals or white crystalline powder[1] | ||
| 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) | ||
| −88.7·10−6 cm3/mol | |||
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| Related compounds | |||
Related Parabens
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Ethylparaben Propylparaben Butylparaben | ||
Related compounds
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Methyl salicylate (ortho isomer) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Template:Chembox Footer/trackingTemplate:Short description
Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula Page Module:Chem2/styles.css has no content.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 insects[3] and is a component of queen mandibular pheromone.
It is a pheromone in wolves produced[<span title="Script error: No such module "decodeEncode".">clarification needed] during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat.[4][5]
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.[12][13]
References
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- ^ Page Module:Citation/CS1/styles.css has no content."Methylparaben Experimental Properties". PubChem.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content."Semiochemical - me-4-hydroxybenzoate". pherobase.com.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.Steven R. Lindsay (2013). Handbook of Applied Dog Behavior and Training, Adaptation and Learning. John Wiley and Sons.
- ^ Page Module:Citation/CS1/styles.css has no content."Bloomington Drosophila Stock Center".
- ^ Page Module:Citation/CS1/styles.css has no content.Gu W, Xie DJ, Hour XW (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.
- ^ a b c d Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content."Parabens". Food and Drug Administration. 9 September 2020. Archived from the original on March 30, 2014.
- ^ Page Module:Citation/CS1/styles.css has no content.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.
- ^ Page Module:Citation/CS1/styles.css has no content.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 Script error: No such module "webarchive". at Household Products Database
- European Commission Scientific Committee on Consumer Products Extended Opinion on the Safety Evaluation of Parabens (2005) [1]
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