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H5501

Sigma-Aldrich

Methyl 4-hydroxybenzoate

ReagentPlus®, ≥99.0%, crystalline

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Synonym(s):
p-Hydroxybenzoic acid methyl ester, Methyl paraben, NIPAGIN
Linear Formula:
HOC6H4CO2CH3
CAS Number:
99-76-3
Molecular Weight:
152.15
Beilstein:
509801
EC Number:
202-785-7
MDL number:
MFCD00002352
PubChem Substance ID:
329815219
NACRES:
NA.25

Quality Level

200

product line

ReagentPlus®

Assay

≥99.0%

form

crystalline

mp

125-128 °C (lit.)

SMILES string

COC(=O)c1ccc(O)cc1

InChI

1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3

InChI key

LXCFILQKKLGQFO-UHFFFAOYSA-N

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Application

Methyl 4-hydroxybenzoate has been used:
  • in sex-linked recessive lethal (SLRL) test in Drosophila melanogaster
  • as a constituent in cream formulation
  • as an antifungal agent in Drosophila melanogaster culture

Biochem/physiol Actions

Methyl 4-hydroxybenzoate, also called methyl paraben or nipagin, comprises the ester of p-hydroxybenzoic acid. It is present naturally in cloudberry, white wine and bourbon vanilla. Methyl 4-hydroxybenzoate has antimicrobial and antifungal functionality and is commercially used as a preservative in the food, cosmetic and pharmaceutical industry. Methyl 4-hydroxybenzoate has cytotoxic effects on keratinocytes in the presence of sunlight. Methyl 4-hydroxybenzoate upon solar irradiation mediates DNA damage and modulates esterase metabolism resulting in skin damage and favors cancer progression. Methyl 4-hydroxybenzoate has estrogenic functionality and upregulates estrogen-related genes.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

The product is not intended for use as a biocide under global biocide regulations, including but not limited to US EPA′s Federal Insecticide Fungicide and Rodenticide Act, European Biocidal Products Regulation, Canada’s Pest Management Regulatory Agency, Turkey’s Biocidal Products Regulation, Korea’s Consumer Chemical Products and Biocide Safety Management Act (K-BPR) and others.

Pictograms

Environment
GHS09

Hazard Statements

H411

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

334.4 °F

Flash Point(C)

168 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Combined activation of methyl paraben by light irradiation and esterase metabolism toward oxidative DNA damage
Okamoto Y, et al.
Chemical Research in Toxicology, 21(8), 1594-1599 (2008)
Methylparaben potentiates UV-induced damage of skin keratinocytes
Handa O, et al.
Toxicology, 227(1-2), 62-72 (2006)
Determination of methylparaben from cosmetic products by ultra performance liquid chromatography.
Mincea M, et al.
J. Serb. Chem. Soc., 74(6), 1335-1373 (2009)
The estrogenicity of methylparaben and ethylparaben at doses close to the acceptable daily intake in immature Sprague-Dawley rats
Sun L, et al.
Scientific Reports, 6, 25173-25173 (2016)
Fruit flies may face a nutrient-dependent life-history trade-off between secondary sexual trait quality, survival and developmental rate
Gray LJ, et al.
Journal of Insect Physiology, 104(8), 60-70 (2018)
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