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E218 Methyl p-hydroxybenzoate is a 4-hydroxybenzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with methanol.
E218 Methyl p-hydroxybenzoate is the most frequently used antimicrobial preservative in cosmetics.
E218 Methyl p-hydroxybenzoate occurs naturally in several fruits, particularly in blueberries.
CAS: 99-76-3
MF: C8H8O3
MW: 152.15
EINECS: 202-785-7
Synonyms
NIPAGIN PLAIN;P-HYDROXYBENZOIC ACID METHYL ESTER;RARECHEM AL BF 0098;METHYLPARABEN,FCC;METHYLPARABEN,NF;4-HYDROXYBENZOICACIDMETHYLESTER(METHYLPARABEN);4-HYDROXYLMETHYLBENZOATE;Methyl-4-hydroxybenzoat
E218 Methyl p-hydroxybenzoatet has a role as a plant metabolite, an antimicrobial food preservative, a neuroprotective agent and an antifungal agent.
E218 Methyl p-hydroxybenzoate is basically a methyl ester of p-hydroxybenzoic acid.
E218 Methyl p-hydroxybenzoate is non-toxic, and non-carcinogenic in nature.
E218 Methyl p-hydroxybenzoate is a stable, non-volatile compound and finds application as an anti-microbial preservative in foods, drugs and cosmetics.
E218 Methyl p-hydroxybenzoate is readily absorbed through the skin and gastrointestinal tract.
Upon hydrolyzation, E218 Methyl p-hydroxybenzoate is hydrolyzed to p-hydroxybenzoic acid, and the conjugates formed get rapidly excreted in the urine.
E218 Methyl p-hydroxybenzoate one of the parabens, is a preservative with the chemical formula CH3O2CC6H4OH.
E218 Methyl p-hydroxybenzoate is the methyl ester of p-hydroxybenzoic acid. Several related esters are known (ethyl-, propyl-, butylparaben).
Together they are the most common preservatives in cosmetics and foods.
Among their advantages, parabens are inexpensive, colorless, stable, odorless, and readily biodegraded.
E218 Methyl p-hydroxybenzoate serves as a pheromone for a variety of insects and is a component of queen mandibular pheromone.
E218 Methyl p-hydroxybenzoate is a pheromone in wolves produced during estrus associated with the behavior of alpha male wolves preventing other males from mounting females in heat.
E218 Methyl p-hydroxybenzoate, known as Methyl P-Hydroxybenzoate, is a food additive in the category of chemical preservatives.
E218 Methyl p-hydroxybenzoate is a derivative of benzoic acid, E 210.
Although E218 Methyl p-hydroxybenzoate is sparingly soluble, it is found in many food and cosmetic products.
As a widely used preservative, E218 Methyl p-hydroxybenzoate helps extend the shelf life of products and prevents the growth of harmful microorganisms.
E218 Methyl p-hydroxybenzoate is a type of paraben, which is a class of chemicals primarily used as preservatives.
E218 Methyl p-hydroxybenzoate's chemical structure is CH3(C6H4(OH)COO).
E218 Methyl p-hydroxybenzoate appears as a white crystalline powder and is known for its antibacterial and antifungal properties, making it a valuable additive in various industries.
E218 Methyl p-hydroxybenzoate, also known as methylparaben (E218), is an organic chemical compound from the paraben group.
E218 Methyl p-hydroxybenzoate's chemical formula is C8H8O3.
E218 Methyl p-hydroxybenzoate is widely used as a preservative in the pharmaceutical, cosmetic and, above all, food industries.
Thanks to its antibacterial and antifungal properties, E218 Methyl p-hydroxybenzoate effectively prolongs the shelf life of products, preventing them from spoiling.
E218 Methyl p-hydroxybenzoate is valued for its low toxicity and good tolerance by the human body, making it one of the safest preservatives available on the market.
However, paraben compounds, including E218 Methyl p-hydroxybenzoate, are under investigation due to potential endocrine effects, making their safe use constantly monitored.
E218 Methyl p-hydroxybenzoate Chemical Properties
Melting point: 125-128 °C (lit.)
Boiling point: 298.6 °C
density: 1,46g/cm
vapor pressure: 0.000005 hPa (20 °C)
FEMA: 2710 | METHYL P-HYDROXYBENZOATE
refractive index: 1.4447 (estimate)
Fp: 280°C
storage temp.: room temp
solubility: ethanol: soluble0.1M, clear, colorless
pka: pKa 8.15(H2O,t =20.0) (Uncertain)
form: Crystalline Powder
color: White to almost white
Odor: odorless or faint char. odor, sl. burning taste
PH: 5.8 (H2O, 20°C) (saturated solution)
biological source: synthetic
Water Solubility: Slightly soluble in water.
FreezingPoint: 131℃
Merck: 14,6107
BRN: 509801
Henry's Law Constant: 4.5×103 mol/(m3Pa) at 25℃, HSDB (2015)
Stability: Stable. Incompatible with strong oxidizing agents, strong bases.
Major Application: flavors and fragrances
Cosmetics Ingredients Functions: PRESERVATIVE FRAGRANCE
Cosmetic Ingredient Review (CIR): Methylparaben (99-76-3)
InChI: 1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChIKey: LXCFILQKKLGQFO-UHFFFAOYSA-N
LogP: 1.98 at 20℃
CAS DataBase Reference: 99-76-3(CAS DataBase Reference)
NIST Chemistry Reference: Benzoic acid, 4-hydroxy-, methyl ester(99-76-3)
EPA Substance Registry System: E218 Methyl p-hydroxybenzoate (99-76-3)
E218 Methyl p-hydroxybenzoate is a colorless crystalline powder with a faint characteristic odor and a slight burning taste.
E218 Methyl p-hydroxybenzoate is slightly soluble in water but easily dissolves in ethanol, ether, acetone, and other organic solvents.
One gram can dissolve in 2.5 ml of ethanol, approximately 4 ml of propylene glycol, or 400 ml of water at 25°C or about 50 ml of water at 80°C.
E218 Methyl p-hydroxybenzoate is commonly used as a fungistat in soft drinks, non-leavened bakery products, and other products, with a permissible level of up to 0.1%.
To inhibit Gram-positive bacteria, 1000 to 4000 ppm are required, and its effectiveness increases with decreasing pH, similar to benzoates.
E218 Methyl p-hydroxybenzoate occurs as colorless crystals or a white crystalline powder.
E218 Methyl p-hydroxybenzoate is odorless or almost odorless and has a slight burning taste.
Soluble in alcohol,ether; slightly soluble in water, benzene, and carbontetrachloride.
E218 Methyl p-hydroxybenzoate has a broad spectrum of antibacterial and antifungal activity.
E218 Methyl p-hydroxybenzoate is stable over a wide pH range, which allows it to be used in a variety of food products.
In addition, E218 Methyl p-hydroxybenzoate is readily soluble in alcohols and some organic solvents, making it easy to incorporate into product formulations.
Content analysis
Method one: determinate according to the content analysis method in "butyl p-hydroxybenzoate (07002)".
Per mL 1 mol/L sodium hydroxide is equivalent to the product (C8H8O3) 152.2mg.
Method two: Take 0.1 g (accurate to 1 mg) of the sample previously dried on silica gel for 5 h and move into a 300 ml flask with a glass plug.
Plus l mol/L sodium hydroxide 10ml, heated in the water bath for 15min.
After cooling, add 0.1mol/L potassium bromate 0.00ml, potassium bromide 5.0g and l mol/L hydrochloric acid 30ml.
Put 15min in the dark room after sealing.
Add potassium iodide 1 g, shake the flask vigorously, with 0.1mol/L sodium thiosulfate titration, with starch test solution (TS-235) as an indicator.
Per ml 0.1mol/L potassium bromate is equivalent to the product (C8H8O3) 25.36mg.
Uses
E218 Methyl p-hydroxybenzoate is the ester of methyl alcohol and p-hydroxybenzoic acid, E218 Methyl p-hydroxybenzoate is a bacteriostatic agent and preservative that was added to local anesthetic agents without vasoconstrictors before 1984 to prevent bacterial growth.
Allergic reactions developed from repeated exposures to parabens led to the removal of this agent from dental anesthetic solutions.
Similar products produced by similar production methods, like ethyl p-hydroxybenzoate (paraben B) and propyl p-hydroxybenzoate (Nepalese c), are also disinfectant preservatives.
The products are irritating to the skin.
E218 Methyl p-hydroxybenzoate is used as an anti-fungal agent.
E218 Methyl p-hydroxybenzoate is also used as a preservative in foods, beverages and cosmetics.
E218 Methyl p-hydroxybenzoate acts as an inhibitor of growth of molds and to lesser extent bacteria and as a vehicle for ophthalmic solution.
E218 Methyl p-hydroxybenzoate is an antimicrobial agent which is a white free-flowing powder.
E218 Methyl p-hydroxybenzoate is active against yeast and molds over a wide ph range. see parabens.
E218 Methyl p-hydroxybenzoate and propylparaben are the most common of these. parabens is one of the most commonly used group of preservatives in the cosmetic, pharmaceutical, and food industries.
Parabens provide bacteriostatic and fungistatic activity against a diverse number of organisms, and are considered safe for use in cosmetics, particularly in light of their low sensitizing potential.
An evaluation of preservatives for use in leave-on cosmetic preparations lists parabens among the least sensitizing.
The range of concentrations used in cosmetics varies between 0.03 and 0.30 percent, depending on the conditions for use and the product to which the paraben is added.
E218 Methyl p-hydroxybenzoate is one of the most popular preservatives in beauty products and food items.
According to the National Library of Medicine, the ingredient occurs naturally in a handful of fruits—like blueberries—though it can also be created synthetically.
E218 Methyl p-hydroxybenzoate's found in everything from cream cleansers and moisturizers to primers and foundations and helps these products maintain their effectiveness.
Rabach says that E218 Methyl p-hydroxybenzoate's chock-full of anti-fungal and antibacterial properties, which work wonders to extend the shelf life of skincare, haircare, and cosmetic products.
E218 Methyl p-hydroxybenzoate is an anti-fungal agent often used in a variety of cosmetics and personal-care products.
E218 Methyl p-hydroxybenzoate is also used as a food preservative and has the E number E218.
E218 Methyl p-hydroxybenzoate is commonly used as a fungicide in Drosophila food media at 0.1%.
To Drosophila, E218 Methyl p-hydroxybenzoate is toxic at higher concentrations, has an estrogenic effect (mimicking estrogen in rats and having anti-androgenic activity), and slows the growth rate in the larval and pupal stages at 0.2%.
E218 Methyl p-hydroxybenzoate is mainly used as a preservative in food products, including beverages, sauces, fruit preparations, as well as in cosmetics and pharmaceutical products.
E218 Methyl p-hydroxybenzoate's presence helps prevent the growth of harmful microorganisms, which contributes to the safety and extended shelf life of products.
Pharmaceutical Applications
E218 Methyl p-hydroxybenzoate is widely used as an antimicrobial preservative in cosmetics, food products, and pharmaceutical formulations.
E218 Methyl p-hydroxybenzoate may be used either alone or in combination with other methylparaben is the most frequently used antimicrobial preservative.
The parabens are effective over a wide pH range and have a broad spectrum of antimicrobial activity, although they are most effective against yeasts and molds.
Antimicrobial activity increases as the chain length of the alkyl moiety is increased, but aqueous solubility decreases; therefore a mixture of parabens is frequently used to provide effective preservation.
Preservative efficacy is also improved by the addition of propylene glycol (2–5%), or by using parabens in combination with other antimicrobial agents such as imidurea;
Owing to the poor solubility of the parabens, paraben salts (particularly the sodium salt) are more frequently used in formulations.
However, this raises the pH of poorly buffered formulations.
E218 Methyl p-hydroxybenzoate (0.18%) together with propylparaben (0.02%) has been used for the preservation of various parenteral pharmaceutical formulations.
Preparation
To prepare the drug, p-hydroxybenzoic acid, and methanol were esterified.
First, excess methanol was added to p-hydroxybenzoic acid and stirred to dissolve.
Concentrated sulfuric acid was then slowly added while stirring.
The mixture was heated and refluxed for 10 hours, before being poured into water to precipitate crystallization.
The crude product was then washed with water, sodium carbonate solution, and water, and recrystallized from water or 25% ethanol to obtain the finished product.
The yield of the drug was 85%.
Raw material consumption for each tonne of product included 1200 kg of p-hydroxybenzoic acid and 1000 kg of methanol.
Preparation
E218 Methyl p-hydroxybenzoate is produced through the methanol esterification of p-hydroxybenzoic acid in the presence of sulfuric acid.
The materials are heated in a glass-lined reactor and distilled under reflux.
The resulting acid is neutralized with caustic soda, then crystallized through cooling.
The crystallized product is centrifuged, washed, dried under vacuum, milled and blended, all in corrosion-resistant equipment to avoid metallic contamination.
Contact allergens
E218 Methyl p-hydroxybenzoate is one of the parabens family.
Parabens are esters formed by p-hydroxybenzoic acid and an alcohol.
They are largely used as biocides in cosmetics and toiletries, medicaments, or food.
They have synergistic power with other biocides.
Parabens can induce allergic contact dermatitis, mainly in chronic dermatitis and wounded skin.
Biochem/physiol Actions
E218 Methyl p-hydroxybenzoate, also called methyl paraben or nipagin, comprises the ester of p-hydroxybenzoic acid.
E218 Methyl p-hydroxybenzoate is present naturally in cloudberry, white wine and bourbon vanilla.
E218 Methyl p-hydroxybenzoate has antimicrobial and antifungal functionality and is commercially used as a preservative in the food, cosmetic and pharmaceutical industry.
E218 Methyl p-hydroxybenzoate has cytotoxic effects on keratinocytes in the presence of sunlight.
E218 Methyl p-hydroxybenzoate upon solar irradiation mediates DNA damage and modulates esterase metabolism resulting in skin damage and favors cancer progression.
E218 Methyl p-hydroxybenzoate has estrogenic functionality and upregulates estrogen-related genes.
