H5501
Methyl 4-hydroxybenzoate
ReagentPlus®, ≥99.0%, crystalline
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All Photos(4)
Synonym(s):
p-Hydroxybenzoic acid methyl ester, Methyl paraben, NIPAGIN
Linear Formula:
HOC6H4CO2CH3
CAS Number:
Molecular Weight:
152.15
Beilstein:
509801
EC Number:
MDL number:
UNSPSC Code:
51452201
PubChem Substance ID:
NACRES:
NA.25
Recommended Products
Quality Level
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.
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2
WGK
WGK 1
Flash Point(F)
334.4 °F
Flash Point(C)
168 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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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)
Determination of methylparaben from cosmetic products by ultra performance liquid chromatography.
Mincea M, et al.
J. Serb. Chem. Soc., 74(6), 1335-1373 (2009)
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)
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)
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