Chemistry:Methylparaben

From HandWiki

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH
3O
2CC
6H
4OH. 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.[1]

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

Methylparaben is practically non-toxic by both oral and parenteral administration in animals.[7] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.[7] 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.[8]

Some controversy exists about whether methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.[9] Methylparaben and propylparaben are considered generally recognized as safe (GRAS) by the USFDA for food and cosmetic antibacterial preservation.[10] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.[7] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body.[7]

Methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage.[11][12]

References

  1. ↑ 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. 
  2. ↑ "Semiochemical - me-4-hydroxybenzoate". pherobase.com. http://www.pherobase.com/database/compound/compounds-detail-me-4-hydroxybenzoate.php. 
  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". https://bdsc.indiana.edu/information/recipes/germanfood.html. 
  6. ↑ "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. 
  7. ↑ 7.0 7.1 7.2 7.3 "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. 
  8. ↑ "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. 
  9. ↑ 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. doi:10.1016/j.watres.2014.09.030. PMID 25462712. Bibcode: 2015WatRe..68....1H. 
  10. ↑ "Parabens". Food and Drug Administration. 9 September 2020. https://www.fda.gov/cosmetics/productsingredients/ingredients/ucm128042.htm. 
  11. ↑ "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. Bibcode: 2006Toxgy.227...62H. 
  12. ↑ "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. 
  • 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



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Methylparaben&oldid=4178903"