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Methylparaben

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(Redirected from Methyl p-hydroxybenzoate)
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.532 Edit this at Wikidata
E number E218 (preservatives)
KEGG
UNII
  • InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 checkY
    Key: LXCFILQKKLGQFO-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
    Key: LXCFILQKKLGQFO-UHFFFAOYAH
  • COC(=O)c1ccc(O)cc1
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 checkY☒N ?)
UV-visible spectrum of methylparaben

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

[edit]

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

[edit]

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

[edit]

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

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  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.
  8. ^ 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.
  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.
[edit]
  • 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]
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