H5501
Methyl 4-hydroxybenzoate
ReagentPlus®, ≥99.0%, crystalline
Synonym(s):
p-Hydroxybenzoic acid methyl ester, Methyl paraben, NIPAGIN
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About This Item
Linear Formula:
HOC6H4CO2CH3
CAS Number:
Molecular Weight:
152.15
UNSPSC Code:
51452201
NACRES:
NA.25
PubChem Substance ID:
EC Number:
202-785-7
Beilstein/REAXYS Number:
509801
MDL number:
Product Name
Methyl 4-hydroxybenzoate, ReagentPlus®, ≥99.0%, crystalline
InChI
1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChI key
LXCFILQKKLGQFO-UHFFFAOYSA-N
SMILES string
COC(=O)c1ccc(O)cc1
product line
ReagentPlus®
assay
≥99.0%
form
crystalline
mp
125-128 °C (lit.)
Quality Level
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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.
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.
Legal Information
ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 2
Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
334.4 °F
flash_point_c
168 °C
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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)
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)
Methylparaben potentiates UV-induced damage of skin keratinocytes
Handa O, et al.
Toxicology, 227(1-2), 62-72 (2006)
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)
Determination of methylparaben from cosmetic products by ultra performance liquid chromatography.
Mincea M, et al.
J. Serb. Chem. Soc., 74(6), 1335-1373 (2009)
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