Methylparaben

Methylparaben
Names
IUPAC name
Methyl 4-hydroxybenzoate
Other names
Methyl paraben;
Methyl p-hydroxybenzoate;
Methyl parahydroxybenzoate;
Nipagin M;
E number E218; Tegosept; Mycocten
Identifiers
99-76-3 Yes
ChEBI CHEBI:31835 
ChEMBL ChEMBL325372 Yes
ChemSpider 7176 Yes
Jmol-3D images Image
KEGG D01400 Yes
PubChem 7456
UNII A2I8C7HI9T Yes
Properties
Molecular formula
 C8H8O3
Molar mass 152.15 g·mol−1
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Related compounds
Related Parabens
Ethylparaben
Propylparaben
Butylparaben
Related compounds
 Methyl salicylate (ortho isomer)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
  verify (what is: Yes/?)
Infobox references

Methylparaben, also 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[1] and is a component of queen mandibular pheromone.

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. To Drosophila, methylparaben is toxic at higher concentrations, has an estrogenic effect, and slows the growth rate in the larval and pupal stages at lower concentrations.[2]

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) for food and cosmetic antibacterial preservation.[3] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.[4] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body.[4] Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and parenteral administration in animals.[4] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.[4]

Studies indicate that methylparaben applied on the skin may react with UVB, leading to increased skin aging and DNA damage.[5][6]

References

  1. ↑ Semiochemical - me-4-hydroxybenzoate, pherobase.com
  2. ↑ Gu Wei (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science 30 (1): 252–254.
  3. ↑ Parabens, Food and Drug Administration
  4. ↑ 4.0 4.1 4.2 4.3 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 Chem. Toxicol. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298.
  5. ↑ Handa, O; Kokura, S; Adachi, S; Takagi, T; Naito, Y; Tanigawa, T; Yoshida, N; Yoshikawa, T (2006). "Methylparaben potentiates UV-induced damage of skin keratinocytes". Toxicology 227 (1–2): 62–72. doi:10.1016/j.tox.2006.07.018. PMID 16938376.
  6. ↑ Okamoto, Yoshinori; Hayashi, Tomohiro; Matsunami, Shinpei; Ueda, Koji; Kojima, Nakao (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