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H5501

Sigma-Aldrich

Methyl 4-hydroxybenzoate

ReagentPlus®, ≥99.0%, crystalline

Synonym(s):

p-Hydroxybenzoic acid methyl ester, Methyl paraben, NIPAGIN

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100 G
£38.40
500 G
£128.00
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£190.00
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£642.00

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100 G
£38.40
500 G
£128.00
1 KG
£190.00
5 KG
£642.00

About This Item

Linear Formula:
HOC6H4CO2CH3
CAS Number:
99-76-3
Molecular Weight:
152.15
Beilstein:
509801
EC Number:
202-785-7
MDL number:
MFCD00002352
UNSPSC Code:
51452201
PubChem Substance ID:
329815219
NACRES:
NA.25

£38.40

Please contact Customer Service for Availability
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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[1]
  • as a constituent in cream formulation[2]
  • as an antifungal agent in Drosophila melanogaster culture[3]

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.[4][5] Methyl 4-hydroxybenzoate has cytotoxic effects on keratinocytes in the presence of sunlight.[6] Methyl 4-hydroxybenzoate upon solar irradiation mediates DNA damage and modulates esterase metabolism resulting in skin damage and favors cancer progression.[7] Methyl 4-hydroxybenzoate has estrogenic functionality and upregulates estrogen-related genes.[8]

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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Certificates of Analysis (COA)

Lot/Batch Number
0000409245
0000409245
0000409267
0000409267
0000403212

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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)
Methylparaben potentiates UV-induced damage of skin keratinocytes
Handa O, et al.
Toxicology, 227(1-2), 62-72 (2006)
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)
Simultaneous Determination of Fusidic Acid, m-and p-Hydroxybenzoates and Butylhydroxyanisole by TLC with Densitometric Detection in UV
Krzek J, et al.
Journal of Liquid Chromatography and Related Technologies, 29(14), 2129-2139 (2006)
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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