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Ethylparaben is an ethyl ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with ethanol, It acts as an antimicrobial food preservative, an antifungal agent, a plant metabolite and a phytoestrogen. This is a paraben and an ethyl ester.
CAS Number: 120-47-8
Chemical nature: Ethyl-4-hydroxybenzoate
EC number : 204-399-4
Synonyms:
Ethylparaben; ETHYL 4-HYDROXYBENZOATE; 120-47-8; Ethyl paraben; Ethyl p-hydroxybenzoate; Mycocten; 4-Hydroxybenzoic acid ethyl ester; Ethyl parasept; Ethyl parahydroxybenzoate; Easeptol; Ethyl butex; p-Hydroxybenzoic acid ethyl ester; Tegosept E; Napagin A; Nipagin A; Nipazin A; Solbrol A; Sobrol A; Benzoic acid, 4-hydroxy-, ethyl ester; p-Carbethoxyphenol; Aseptoform E; Mekkings E; Aseptin A; Bonomold OE; Ethyl p-oxybenzoate; Ethyl-p-hydroxybenzoate; Ethyl-4-hydroxybenzoate; Ethyl para-hydroxybenzoate; p-Oxybenzoesaeureaethylester; 4-Hydroxy-benzoic acid ethyl ester; 4-Carbethoxyphenol; NSC 23514; p-Hydroxybenzoate ethyl ester; Ethylparaben [NF]; 9001-05-2; UNII-14255EXE39; 4-Hydroxybenzoic acid, ethyl ester; 4-(Ethoxycarbonyl)phenol; Para-hydroxybenzoic acid ethyl ester; Ethylester kyseliny p-hydroxybenzoove; MFCD00002353; Benzoic acid, p-hydroxy-, ethyl ester; Ester etylowykwasu p-hydroksybenzoesowego; E214; Ethylparaben (NF); 14255EXE39; NCGC00160654-01; Carbethoxyphenol; DSSTox_CID_2528; WLN: QR DVO2; DSSTox_RID_76615; DSSTox_GSID_22528; Ethyl 4-hydroxybenzoate, 99%; Caswell No. 447; p-Hydroxybenzoic acid, ethyl ester; CAS-120-47-8; HSDB 938; EINECS 204-399-4; p-Oxybenzoesaeureaethylester [German]; EPA Pesticide Chemical Code 061202; BRN 1101972; Ethyl chemosept; AI3-30960; Aseptine aEthylparaben; ETHYL 4-HYDROXYBENZOATE; 120-47-8; Ethyl paraben; Ethyl p-hydroxybenzoate; Mycocten; 4-Hydroxybenzoic acid ethyl ester; Ethyl parasept; Ethyl parahydroxybenzoate; Easeptol; Ethyl butex; p-Hydroxybenzoic acid ethyl ester; Tegosept E; Napagin A; Nipagin A; Nipazin A; Solbrol A; Sobrol A; Benzoic acid, 4-hydroxy-, ethyl ester; p-Carbethoxyphenol; Aseptoform E; Mekkings E; Aseptin A; Bonomold OE; Ethyl p-oxybenzoate; Ethyl-p-hydroxybenzoate; Ethyl-4-hydroxybenzoate; Ethyl para-hydroxybenzoate; p-Oxybenzoesaeureaethylester; 4-Hydroxy-benzoic acid ethyl ester; 4-Carbethoxyphenol
Ethylparaben. Nipagin® A is a water-soluble preservative. It offers broad spectrum of activity against bacteria and fungi. It is a short-chain paraben for higher water solubility. It exhibits low order of toxicity and effectiveness at low concentrations. It has stability over a broad pH-range and global acceptance in personal care applications. Nipagin® A shows good biodegradability at environmental concentrations. It is used in syndets & bar soaps, shampoos & showers products, liquid soaps, wet wipes, hair conditioners, antiperspirants & deodorants, hair styling products, creams, lotions and decorative cosmetics.Nipagin™ A is a broad spectrum antimicrobial agent designed for preservation of a wide range of cosmetics, toiletries and topical pharmaceuticals. it is suitable for both rinse-off and leave-on formulations. This product is supplied as a white, or almost white crystalline powder.Almost odourless, small, colourless crystals or a white, crystalline powder.Small, colorless crystals or powder at room temperature.Crystals from dilute alcohol.Nipagin A is a broad spectrum antimicrobial agent designed for preservation of a wide range of cosmetics,toiletries and topical pharmaceuticals. Nipagin A is suitable to preserve both rinse- off and leave- on formulations.Typical use concentrations of Nipagin A is 0.1 – 0.3 %. Combinations of p- Hydroxybenzoic acid esters, e.g. with Nipasol M, Nipagin M or Nipabutyl exhibit increased activity compared with individual esters.Nipagin A is freely soluble in most oils, waxes, fatty alcohols, but have relatively low solubility in water. The low aqueous solubility does not affect the microbiological efficacy of the esters. Most formulations requiring preservation contain a significant amount of water. This may mean that Nipagin A cannot readily be added directly to the formulation. Other methods of incorporation are quite straightforward however, and are listed below.The solubility of Nipagin A increases greatly as the temperature of the water rises. Therefore a concentrate may be made up by heating an appropriate quantity of water to 60- 100 °C prior to addition of Nipagin A. This concentrate may then be added to the formulation, provided that the ester concentration does not exceed its solubility in the formulation at normal ambient temperatures. Nipagin A is readily soluble in polar organic solvents. Where such a solvent is already part of a formulation an Nipagin A concentrate may be made up prior to addition. If a suitable solvent is not already part of theformulation, a highly concentrated solution may be made up e.g. 32 % in Ethanol, which would give insignificant residual levels of ethanol in the end product. Nipagin A is readily soluble in lipophilic ingredients and may be introduced to a formulation by adding to the oil phase with some warming before any emulsification stage. In multiphase systems, such as emulsions, it is often advisable to use a combination of aqueous dissolution with either of the other methods to ensure adequate preservation. The ester may be incorporated in the water to its maximum solubility and any further quantities may be dissolved in the oil phase, or solvent, as appropriate. Nipagin A remains fully stable over a wide pH range from 4- 8. In general the lower the pH of the formulation, the more active is Nipagin A. That can result in a lower use concentration when the pH of the formulation is more acidic.
Nipagin A is a short-chain paraben for higher water solubility.
Benefits
Broad spectrum of activity against bacteria and fungi
Low order of toxicity
Effectiveness at low concentrations
Stability over a broad pH-range
Water-soluble
Biodegradability at environmental concentrations
Global acceptance in personal care applications
Chemical name
Ethyl 4-Hydroxybenzoate
INCI designation
Ethylparaben
Product properties *)
Appearance (20°C): White, or almost white crystalline powder.
Chemical and physical data
Melting point: 115 - 118 oC
Assayacc. BP/PH.Eur: 98.0 - 102.0 %
IUPAC name
Ethyl 4-hydroxybenzoate
Other names
Ethyl paraben;
Ethyl parahydroxybenzoate;
Ethyl para-hydroxybenzoate;
Ethyl p-hydroxybenzoate;
4-Hydroxybenzoic acid ethyl ester
Identifiers
CAS Number: 120-47-8
Ethylparaben is an ethyl ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with ethanol, It has a role as an antimicrobial food preservative, an antifungal agent, a plant metabolite and a phytoestrogen. It is a paraben and an ethyl ester.
Antimicrobial Preservative Used in Cosmetics and Personal Care.
Uses
Nipagin A is a broad spectrum antimicrobial agent designedfor preservation of a wide range of cosmetics, toiletries and topical pharmaceuticals.Nipagin A is suitable to preserve both rinse- off and leave- on formulations.
Applications
Typical use concentrations of Nipagin A is 0.1 – 0.3 %.Combinations of p- Hydroxybenzoic acid esters, e.g. with Nipasol M, Nipagin M or Nipabutyl exhibit increased activity compared with individual esters.
Incorporation
Nipagin A is freely soluble in most oils, waxes, fatty alcohols, but have relatively low solubility in water.The low aqueous solubility does not affect the microbiological efficacy of the esters.Most formulations requiring preservation contain a significant amount of water.This may mean that Nipagin A cannot readily be added directly to the formulation.Other methods of incorporation are quite straightforward however, and are listed below.Ethylparaben (ethyl para-hydroxybenzoate) is the ethyl ester of p-hydroxybenzoic acid. Its formula is HO-C6H4-CO-O-CH2CH3. It is a member of the class of compounds known as parabens.It is used as an antifungal preservative. As a food additive, it has E number E214.Sodium ethyl para-hydroxybenzoate, the sodium salt of ethylparaben, has the same uses and is given the E number E215.
Dissolving in water
The solubility of Nipagin A increases greatly as the temperature of the water rises.
Therefore a concentrate may be made up by heating an appropriate quantity of water to 60- 100 °C prior to addition of Nipagin A.
This concentrate may then be added to the formulation, provided that the ester concentration does not exceed its solubility in the formulation at normal ambient temperatures.
Dissolving in organic solvents Nipagin A is readily soluble in polar organic solvents.
Where such a solvent is already part of a formulation an Nipagin A concentrate may be made up prior to addition.
If a suitable solvent is not already part of the formulation,a highly concentrated solution may be madeup e.g. 32 % in Ethanol, which would give insignificant residual levels of ethanol in the end product.
Solubilisation in oils, emulsifiers etc.
Nipagin A is readily soluble in lipophilic ingredients and may be introduced to a formulation by adding to the oil phase with some warming before any emulsification stage.
In multiphase systems, such as emulsions, it is often advisable to use a combination of aqueous dissolution with either of the other methods to ensure adequate preservation.
The ester may be incorporated in the water to its maximum solubility and any further quantities may be dissolved in the oil phase, or solvent, as appropriate.
pH stability
Nipagin A remains fully stable over a wide pH range from 4- 8.
In general the lower the pH of the formulation, the more active is Nipagin A.
That can result in a lower use concentration when the pH of the formulation is more acidic.
Temperature stability
Nipagin A is stable up to 80 °C
Solubility
The solubility of Nipagin A in different solvents is illustrated
in the following table.
Solvent % (w/w)
Water 10 °C 0.06
Water 25 °C 0.11
Water 80 °C 0.86
Water 100 °C 1.7
Acetone 46
Methanol 45
Ethanol 41
Propylene Glycol 20
Glycerol 0.5
Vegetable oils (arachis) 1.0
Liquid paraffin 0.025
Microbial Activity
Nipagin A exhibits microbiostatic activity against a wide range of bacteria, yeast and mould.
This is illustrated by the following table which shows the minimum inhibitory concentration (MIC) of Nipagin A against examples of different groups of microorganisms.
Microorganisms MIC level (%)
Gram Negative Bacteria
Pseudomonas aeruginosa 0.10
Escherichia coli 0.05
Klebsiella aerogenes 0.05
Klebsiella pneumoniae 0.05
Serratia marcescens 0.05
Proteus vulgaris 0.06
Salmonella enteritidis 0.05
Salmonella typhi 0.10
Microorganisms MIC level (%)
Gram Positive Bacteria
Stpahylococcus aureus 0.07
Streptococcus haemolyticus 0.06
Bacillus cereus 0.025
Bacillus subtilis 0.10
Lactobacillus buchneri 0.06
Yeasts
Candida albicans 0.07
Saccharomyces cerevisiae 0.05
Molds
Aspergillus niger 0.04
Penicillium digitatum 0.025
Rhizopus nigricans 0.025
Chemical Properties
white crystalline powder
Chemical Properties
Ethylparaben occurs as a white, odorless or almost odorless, crystalline powder.
Uses
An antimicrobial
Uses
bronchodilator, tocolytic
Uses
Preservative for pharmaceuticals.
Production Methods
Ethylparaben is prepared by the esterification of p-hydroxybenzoic acid with ethanol (95%).
Synthesis Reference(s)
The Journal of Organic Chemistry, 39, p. 3343, 1974 DOI: 10.1021/jo00937a007
Pharmaceutical Applications
Ethylparaben is widely used as an antimicrobial preservative in cosmetics,food products, and pharmaceutical formulations.
It may be used either alone or in combination with other paraben esters or with other antimicrobial agents. In cosmetics it is one of the most frequently used preservatives.
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.
Owing to the poor solubility of the parabens, paraben salts, particularly the sodium salt, are frequently used. However, this may cause the pH of poorly buffered formulations to become more alkaline.
Contact allergens
This substance 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.
storage
Aqueous ethylparaben solutions at pH 3–6 can be sterilized by autoclaving, without decomposition. At pH 3–6, aqueous solutions are stable (less than 10% decomposition) for up to about 4 years at room temperature, while solutions at pH 8 or above are subject to rapid hydrolysis (10% or more after about 60 days at room temperature).
Ethylparaben should be stored in a well-closed container in a cool, dry place.
Incompatibilities
The antimicrobial properties of ethylparaben are considerably reduced in the presence of nonionic surfactants as a result of micellization. Absorption of ethylparaben by plastics has not been reported, although it appears probable given the behavior of other parabens. Ethylparaben is coabsorbed on silica in the presence of ethoxylated phenols. Yellow iron oxide, ultramarine blue, and aluminum silicate extensively absorb ethylparaben in simple aqueous systems, thus reducing preservative efficacy.
Ethylparaben is discolored in the presence of iron and is subject to hydrolysis by weak alkalis and strong acids.
Regulatory Status
Accepted as a food additive in Europe. Included in the FDA Inactive Ingredients Database (oral, otic, and topical preparations). Included in nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Ethylparaben
* A preservative found in skin care products, often used to treat dry skin through essential oils such as eucalyptus and primrose oil * Read the following TIA articles concerning ethylparaben and its link to cancer: Preservatives and Parabens and Are They Safe? and What Is It: Estrogen in my Shampoo
Ethylparaben is a paraben and preservative found in many skin care products, ranging from skin cream to body lotion to deodorant. It can be found in essential oils used to treat dry skin and in primrose oil serving as an anti-septic. Although parabens are generally considered safe when used in low percentages (.04% - .08%), a study claimed to have found a link between parabens and breast cancer. According to the Cosmetic Ingredient Review (CIR) Expert Panel, however, "the available acute, subchronic, and chronic toxicity tests, using a range of exposure routes, demonstrate a low order of parabens' toxicity at concentrations that would be used in cosmetics" (source). After testing different levels of exposure to parabens in women, men, and children, the CIR Expert Panel found that these "determinations are conservative and likely represent an overestimate of the possibility of an adverse effect (e.g., use concentrations may be lower, penetration may be less) and support the safety of cosmetic products in which parabens preservatives are used."
* A preservative found in skin care products, often used to treat dry skin through essential oils such as eucalyptus and primrose oil
* Read the following TIA articles concerning ethylparaben and its link to cancer: Preservatives and Parabens and Are They Safe? and What Is It: Estrogen in my Shampoo
Functions:
Ethylparaben is a paraben and preservative found in many skin care products, ranging from skin cream to body lotion to deodorant. It can be found in essential oils used to treat dry skin and in primrose oil serving as an anti-septic. Although parabens are generally considered safe when used in low percentages (.04% - .08%), a study claimed to have found a link between parabens and breast cancer. According to the Cosmetic Ingredient Review (CIR) Expert Panel, however, "the available acute, subchronic, and chronic toxicity tests, using a range of exposure routes, demonstrate a low order of parabens' toxicity at concentrations that would be used in cosmetics" (source). After testing different levels of exposure to parabens in women, men, and children, the CIR Expert Panel found that these "determinations are conservative and likely represent an overestimate of the possibility of an adverse effect (e.g., use concentrations may be lower, penetration may be less) and support the safety of cosmetic products in which parabens preservatives are used."
Ultimately, the cosmetics industry has found the low levels of parabens in cosmetics to be safe and the connection between parabens and breast cancer to be weak. The FDA finds that although parabens can mimic estrogen, the actual effects of this low level of activity on the body do not cause cancer in a higher incidence than naturally occurring estrogen. Nonetheless, many paraben-free products are being created to avoid the possible dangers of ethylparaben and other paraben-based preservatives.
Roles Classification
Biological Role(s): antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
phytoestrogen
Any compound produced by a plant that happens to have estrogenic activity.
Application(s): antimicrobial food preservative
A food preservative which prevents decomposition of food by preventing the growth of fungi or bacteria. In European countries, E-numbers for permitted food preservatives are from E200 to E299, divided into sorbates (E200-209), benzoates (E210-219), sulfites (E220-229), phenols and formates (E230-239), nitrates (E240-259), acetates (E260-269), lactates (E270-279), propionates (E280-289) and others (E290-299).
Ethylparaben provides the good performance against Gram positive bacteria exhibited by all the parabens and has the same limitations regarding pH range (acidic only), system compatibility (avoid high levels of ethoxylates) and water solubility (limited). Ethylparaben has been used in combination with Propylparaben in oral preparations for controlling fermentative action. It can be used alone, but is generally used at 0.10 to 0.25% levels with other CoSepts as the antifungal portion of the preservative system.
Use: Ethylparaben is mainly used as antiseptics in cosmetics, food and medicine. It is also can be used as feed preservatives and antiseptic for bacteria.
Use: Preservative, Cosmetics, Feed, Pharmaceutical, Soft Drink, Alcohol Beverage, Beverage Powder, Fruit Juice, Puddings, Sauces, Baking Food, Sauage, Flavoring Agent.
Other names: Benzoic acid, 4-hydroxy-, ethyl ester; Benzoic acid, p-hydroxy-, ethyl ester; p-Carbethoxyphenol; p-Hydroxybenzoate ethyl ester; p-Hydroxybenzoic acid ethyl ester; Aseptoform E; Bonomold OE; Easeptol; Ethyl p-hydroxybenzoate; Ethyl parasept; Ethyl Butex; Ethyl 4-hydroxybenzoate; Mycocten; Napagin A; Nipagin A; Nipazin A; Sobrol A; Solbrol A; Tegosept E; 4-Hydroxybenzoic acid, ethyl ester; Ethyl para-hydroxybenzoate; Ester etylowykwasu p-hydroksybenzoesowego; Ethylester kyseliny p-hydroxybenzoove; Ethyl p-oxybenzoate; Nipagina A; p-Oxybenzoesaeureaethylester; 4-(Ethoxycarbonyl)phenol; 4-Carbethoxyphenol; Aseptin A; Aseptine A; Para-hydroxybenzoic acid ethyl ester; Mekkings E; NSC 23514
Ethylparaben (Ethyl parahydroxybenzoate, Ethyl 4-hydroxybenzoate) is the ethyl ester of p-hydroxybenzoic acid, used as an antifungal preservative and food additive. It is a standardized chemical allergen. The physiologic effect of ethylparaben is by means of Increased Histamine Release, and Cell-mediated Immunity.
Ethylparaben is the ethyl ester of p-hydroxybenzoic acid, used as an antifungal preservative and food additive
Storage instructions
The product must be stored in tighly closed container in a cool, well- ventilated, dry place.
Further information on handling, storage and dispatch isgiven in the EC safety data sheet.
