Chemistry:Methylparaben
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| Names | |||
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| Preferred IUPAC name
Methyl 4-hydroxybenzoate | |||
| Other names
Methyl paraben;
Methyl p-hydroxybenzoate; Methyl parahydroxybenzoate; Nipagin M; E number E218; Tegosept; Mycocten | |||
| Identifiers | |||
3D model (JSmol)
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| ChEMBL | |||
| ChemSpider | |||
| KEGG | |||
PubChem CID
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| UNII | |||
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| Properties | |||
| C8H8O3 | |||
| Molar mass | 152.149 g·mol−1 | ||
| Appearance | Colorless crystals or white crystalline powder[1] | ||
| UV-vis (λmax) | 255 nm (methanol) | ||
| −88.7·10−6 cm3/mol | |||
| Hazards | |||
| NFPA 704 (fire diamond) | |||
| 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). | |||
 verify (what is   ?)
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| Infobox references | |||
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. https://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties.
- ↑ "Semiochemical - me-4-hydroxybenzoate". pherobase.com. http://www.pherobase.com/database/compound/compounds-detail-me-4-hydroxybenzoate.php.
- ↑ 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". https://bdsc.indiana.edu/information/recipes/germanfood.html.
- ↑ "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science 30 (1): 252–254. 2009. http://www.spkx.net.cn/EN/Y2009/V30/I1/252.
- ↑ "Parabens". Food and Drug Administration. 9 September 2020. https://www.fda.gov/cosmetics/productsingredients/ingredients/ucm128042.htm.
- ↑ 8.0 8.1 8.2 8.3 "Evaluation of the health aspects of methyl paraben: a review of the published literature". Food and Chemical Toxicology 40 (10): 1335–73. October 2002. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298.
- ↑ "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. 2008. doi:10.1080/10915810802548359. PMID 19101832.
- ↑ "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology 227 (1–2): 62–72. October 2006. doi:10.1016/j.tox.2006.07.018. PMID 16938376.
- ↑ "Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage". Chemical Research in Toxicology 21 (8): 1594–9. August 2008. doi:10.1021/tx800066u. PMID 18656963.
External links
- Methylparaben at Hazardous Substances Data Bank
- Methylparaben at Household Products Database
- European Commission Scientific Committee on Consumer Products Extended Opinion on the Safety Evaluation of Parabens (2005) [1]
ja:メチルパラベン
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