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Ethylparaben

Alias: NSC23514; NSC 23514; Ethylparaben
Cat No.:V16766 Purity: ≥98%
Ethylparaben is the ethyl ester of paraben and is used as an antifungal preservative and food additive.
Ethylparaben
Ethylparaben Chemical Structure CAS No.: 120-47-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Ethylparaben:

  • Ethylparaben-d4 (Ethyl parahydroxybenzoate-d4; Ethyl 4-hydroxybenzoate-d4)
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Top Publications Citing lnvivochem Products
Product Description
Ethylparaben is the ethyl ester of paraben and is used as an antifungal preservative and food additive.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Ethyl paraben (0-20 mg/mL) demonstrates antimicrobial and antifungal properties against several pathogens [1].
ln Vivo
Ethyl paraben (0–40 mg/kg, intragastrically) raises the levels of estrogen hormone response genes and the estrogen weight of SD estrogen [1].
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Following oral administration, parabens are rapidly absorbed, metabolized, and excreted. Metabolic responses and transformations in mammals vary depending on ester chain length, animal species, route of administration, and test dose. The metabolism of parabens in humans appears to be most similar to that in dogs. The excretion rate of metabolites appears to decrease with increasing ester molecular weight. /4-Hydroxybenzoate (parabens)/ …Deposition of parabens in dogs. Except for butyl ester, which had a recovery rate of 40%, the urinary recovery rates of other esters ranged from 50% to 95%. /It/ …It is concluded that esters are well absorbed, and ester bond hydrolysis and metabolic conjugation are the main elimination pathways. Similar metabolic mechanisms…in humans. Parabens
This study investigated the permeation of methylparaben, ethylparaben, propylparaben, and butylparaben in untreated and lipid-depleted isolated guinea pig dorsal skin, and the effects of three permeation enhancers—N-dodecyl-2-pyrrolidone (laurylpyrrolidone), ethanol, and a mixture of menthol and ethanol—on these parabens. The relationship between the permeability of these parabens and their octanol/water partition coefficients was also investigated, as well as the effects of the permeation enhancers on the fluidity of liposomes containing stratum corneum lipids. The results showed that in untreated guinea pig skin, the permeability of these parabens was positively correlated with their octanol/water partition coefficients. In lipid-depleted guinea pig skin, the permeability of parabens increased, and this was not correlated with their octanol/water partition coefficients. The effects of the permeation enhancers on paraben permeation varied. The osmosis enhancer increased the fluidity of the liposome lipid bilayer. Following intravenous infusion of ethylparaben in dogs, unhydrolyzed ethylparaben was found only in brain tissue. In the liver, kidneys, and muscle, it was immediately hydrolyzed to para-hydroxybenzoic acid. Six hours after oral administration of 1.0 g/kg ethylparaben to dogs, the peak plasma concentrations of free and total ethylparaben reached 427 and 648 μg/cm³, respectively. After 48 hours, all ethylparaben was completely cleared. Metabolism/Metabolites: Para-hydroxybenzoic acid is produced in pigs and Aspergillus. /Excerpt from Table/ Para-hydroxybenzoic acid esters are well absorbed in dogs, with ester bond hydrolysis and metabolic conjugation being the main clearance pathways. Similar metabolic patterns have been observed in humans. Parabens
Orally administered 14C-labeled ethyl paraben contains two major metabolites in the urine of cats: p-hydroxyhippuric acid and free p-hydroxybenzoic acid.
In mice, rats, rabbits, pigs, or dogs, ethyl paraben is excreted in urine as unmodified benzoate, p-hydroxybenzoic acid, p-hydroxyhippuric acid (p-hydroxybenzoylglycine), ester glucuronide, ether glucuronide, or ether sulfate.
For more complete metabolite/metabolite data on ethyl paraben (7 metabolites in total), please visit the HSDB record page.
Known human metabolites of ethyl paraben include (2S,3S,4S,5R)-6-(4-ethoxycarbonylphenoxy)-3,4,5-trihydroxyoxacyclohexane-2-carboxylic acid.
Toxicity/Toxicokinetics
Toxicity Summary
Identification and Uses: Ethyl parabens form colorless small crystals or a white powder. Ethyl parabens inhibits the growth of fungi and bacteria and is used as a preservative in pharmaceuticals, adhesives, and various cosmetic preparations. Human Exposure and Toxicity: Ethyl parabens are irritating to human skin. One human study did not find any sensitizing effects. Parabens are a class of general substances and rarely cause sensitization when applied to intact human skin. Application to damaged skin is a more common cause of sensitization. Oral administration of a mixture of methylparaben, ethylparaben, and propylparaben has been shown to exacerbate pre-existing skin problems. Animal Studies: Ethyl parabens are irritating to the eyes of rabbits. In laboratory animals, acute oral toxicity of ethylparaben is low. Limited long-term studies in rats have shown that ethylparaben has low toxicity and no carcinogenic activity was found. Dietary addition of ethylparaben can lead to proliferation of forestomach cells in rats. Limited Ames bacterial assays did not reveal mutagenicity. Ethylparaben did increase chromosomal aberrations in Chinese hamster ovarian cells, but similar effects were not observed in rats treated with ethylparaben. Oral administration of ethylparaben to pregnant female rats resulted in fetal toxicity at doses reaching maternal toxicity levels. Ethylparaben was not teratogenic in rats. An in vitro study showed that ethylparaben at concentrations as low as 8 mg/mL caused loss of sperm motility; however, an in vivo study showed that adding 0.1% or 1.0% ethylparaben to the diet of mice did not produce sperm toxicity.
Interactions
The biological metabolic pathway of ethylparaben when co-administered with salicylic acid differs from that previously reported when ethylparaben was used alone.
The excretion of the hydrolysis product of ethylparaben—unconjugated paraben—is increased, while the excretion of the glycine conjugates of paraben—para-hydroxyhippuric acid and its ester glucuronide—is decreased. Blood concentration patterns differ significantly from those observed with ethylparaben alone, particularly with delayed elimination of all metabolites. Pharmacokinetic analysis of blood concentration data also revealed the effect of salicylic acid on the biometabolism of ethylparaben.
Non-human toxicity values
LD50 Rat (female) oral 4.30 g/kg
LD50 Rat oral 11.0 g/kg
LD50 Guinea pig oral 2.0 g/kg /from table/
LD50 Rabbit oral 5.0 g/kg /from table/
For more non-human toxicity values (complete data) for ethylparaben (9 items in total), please visit the HSDB record page.
References

[1]. The estrogenicity of methylparaben and ethylparaben at doses close to the acceptable daily intake in immature Sprague-Dawley rats. Sci Rep. 2016 Apr 28;6:25173.

[2]. Identification of ethylparaben as the antimicrobial substance produced by Brevibacillus brevis FJAT-0809-GLX. Microbiol Res. 2015 Mar;172:48-56.

Additional Infomation
Ethyl paraben is an ethyl ester formed by the condensation of the carboxyl group of 4-hydroxybenzoic acid with ethanol. It functions as an antibacterial food preservative, antifungal agent, plant metabolite, and phytoestrogen. It is both a preservative and an ethyl ester. Ethyl paraben is a standardized chemical allergen. Its physiological effects are achieved through increased histamine release and cell-mediated immunity. Ethyl paraben has been reported in Aeschynanthus bracteatus, Inula salsoloides, and other organisms with relevant data. Ethyl paraben is present in alcoholic beverages. It is an antibacterial and preservative. It is found in red wine, white wine, and sake. Ethyl paraben belongs to the hydroxybenzoic acid derivative family. These compounds contain hydroxybenzoic acid (or its derivatives), which refers to a benzene ring with a carboxylic acid group. Ethyl 4-hydroxybenzoic acid is a metabolite found or produced in Saccharomyces cerevisiae.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H10O3
Molecular Weight
166.18
Exact Mass
166.062
CAS #
120-47-8
Related CAS #
Ethylparaben-d4;1219795-53-5
PubChem CID
8434
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
297.5±0.0 °C at 760 mmHg
Melting Point
114-117 °C(lit.)
Flash Point
120.3±12.6 °C
Vapour Pressure
0.0±0.6 mmHg at 25°C
Index of Refraction
1.539
LogP
2.4
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
12
Complexity
148
Defined Atom Stereocenter Count
0
InChi Key
NUVBSKCKDOMJSU-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H10O3/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
Chemical Name
ethyl 4-hydroxybenzoate
Synonyms
NSC23514; NSC 23514; Ethylparaben
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~601.79 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (15.04 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.0176 mL 30.0879 mL 60.1757 mL
5 mM 1.2035 mL 6.0176 mL 12.0351 mL
10 mM 0.6018 mL 3.0088 mL 6.0176 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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