Methylparaben

This article is about this particular compound. For the class of hydroxybenzoate esters, including discussion on possible health effects, see paraben.

Methylparaben
IUPAC name Methyl 4-hydroxybenzoate
Other names Methyl paraben; Methyl p-hydroxybenzoate; Methyl parahydroxybenzoate; Nipagin M; E number E218; Tegosept; Mycocten
Identifiers
CAS number	99-76-3 Y
PubChem	7456
ChemSpider	7176 Y
UNII	A2I8C7HI9T Y
KEGG	D01400 Y
ChEMBL	CHEMBL325372 Y
Jmol-3D images	Image 1
SMILES COC(=O)c1ccc(cc1)O
InChI InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Y Key: LXCFILQKKLGQFO-UHFFFAOYSA-N Y InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Key: LXCFILQKKLGQFO-UHFFFAOYAH
Properties
Molecular formula	C8H8O3
Molar mass	152.15 g mol−1
Related compounds
Related Parabens	Ethylparaben Propylparaben Butylparaben
Related compounds	Methyl salicylate (ortho isomer)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Occurrence

Methylparaben is found in several fruits, particularly blueberries,^[1][2][3] where it acts as an antimicrobial agent.

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. Usage of methylparaben is known to slow Drosophila growth rate in the larval and pupal stages.^{[citation needed]}

Safety

Methylparaben is produced naturally and found in several fruits, primarily blueberries, along with other parabens. There is no evidence that methylparaben or propylparabens are harmful at concentrations typically used in body care or cosmetics.^[4] Methylparaben and propylparaben are considered generally recognized as safe (GRAS) for food and cosmetic antibacterial preservation.^[5] Methylparaben is readily metabolized by common soil bacteria, making it completely biodegradable.

Methylparaben is readily absorbed from the gastrointestinal tract or through the skin.^[6] It is hydrolyzed to p-hydroxybenzoic acid and rapidly excreted in urine without accumulating in the body.^[6] Acute toxicity studies have shown that methylparaben is practically non-toxic by both oral and parenteral administration in animals.^[6] In a population with normal skin, methylparaben is practically non-irritating and non-sensitizing; however, allergic reactions to ingested parabens have been reported.^[6] Methylparaben is not carcinogenic, mutagenic, teratogenic or embryotoxic; additionally, it is negative in the uterotrophic assay.

Studies indicate that methylparaben applied on the skin may react with UVB leading to increased skin aging and DNA damage.^[7][8]

References

1. ^ Al-Shamma A, Drake S, Flynn DL, Mitscher LA, Park YH, Rao GSR, Simpson A, Swayze JK, Veysoglu T, Wu STS (1981). "Antimicrobial Agents From Higher Plants. Antimicrobial Agents From Peganum harmala Seeds". J Nat Prod 44 (6): 745–747. doi:10.1021/np50018a025. PMID 7334386. 
2. ^ Bais HP, Vepachedu R, Vivanco JM, (1 April 2003). "Root specific elicitation and exudation of fluorescent beta-carbolines in transformed root cultures of Oxalis tuberosa". Plant Physiology and Biochemistry 41 (4): 345–353. doi:10.1016/S0981-9428(03)00029-9. 
3. ^ "In Vitro Cellular and Developmental Biology". Plant 37 (6): 730–741. 2001. 
4. ^ Database of Select Committee on GRAS Substances (SCOGS) Reviews: Methyl Paraben
5. ^ Parabens, Food and Drug Administration
6. ^ ^{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 Chem. Toxicol. 40 (10): 1335–73. doi:10.1016/S0278-6915(02)00107-2. PMID 12387298. http://linkinghub.elsevier.com/retrieve/pii/S0278691502001072. 
7. ^ 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. 
8. ^ 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

• Methylparaben at Hazardous Substances Data Bank
• Methylparaben at Household Products Database