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
CAS Number	99-76-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:31835 ;
ChEMBL	ChEMBL325372 ;
ChemSpider	7176 ;
ECHA InfoCard	100.002.532
E number	E218 (preservatives)
IUPHAR/BPS	6273;
KEGG	D01400 ;
PubChem CID	7456;
UNII	A2I8C7HI9T ;
CompTox Dashboard (EPA)	DTXSID4022529 ;
	InChI InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Key: LXCFILQKKLGQFO-UHFFFAOYSA-N ; InChI=1/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3 Key: LXCFILQKKLGQFO-UHFFFAOYAH;
	SMILES COC(=O)c1ccc(cc1)O;
Properties
Chemical formula	C8H8O3
Molar mass	152.149 g·mol−1
Appearance	Colorless crystals or white crystalline powder
UV-vis (λmax)	255 nm (methanol)
Hazards
NFPA 704 (fire diamond)	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). verify (what is ?) 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^[2] and is a component of queen mandibular pheromone. Some plants produce methylparaben, example thale cress.^[3] It is commonly used in the preparation of liquid dosage forms.

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.^[4]

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.^[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]

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

References

^ https://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties
^ Semiochemical - me-4-hydroxybenzoate, pherobase.com
^ Walker TS, Bais HP, Halligan KM, Stermitz FR, Vivanco JM (2003). "Metabolic profiling of root exudates of Arabidopsis thaliana". Journal of Agricultural and Food Chemistry. 51 (9): 2548–54. doi:10.1021/jf021166h. PMID 12696935.
^ Gu Wei (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.
^ Parabens, Food and Drug Administration
^ ^a ^b ^c ^d Soni MG, Taylor SL, Greenberg NA, Burdock GA (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.
^ 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.
^ 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

[1] ttps://pubchem.ncbi.nlm.nih.gov/compound/Methyl_4-hydroxybenzoate#section=Experimental-Properties

[2] Semiochemical - me-4-hydroxybenzoate, pherobase.com

[3] Walker TS, Bais HP, Halligan KM, Stermitz FR, Vivanco JM (2003). "Metabolic profiling of root exudates of Arabidopsis thaliana". Journal of Agricultural and Food Chemistry. 51 (9): 2548–54. doi:10.1021/jf021166h. PMID 12696935.

[4] Gu Wei (2009). "Toxicity and Estrogen Effects of Methyl Paraben on Drosophila melanogaster". Food Science. 30 (1): 252–254.

[5] Parabens, Food and Drug Administration

[Soni-6] Soni MG, Taylor SL, Greenberg NA, Burdock GA (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.

[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.

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