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NIPAGIN A

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. 
Nipagin A formula is HO-C6H4-CO-O-CH2CH3. 
Nipagin A is a member of the class of compounds known as parabens.

Nipagin A is used as an antifungal preservative. 
As a food additive, Nipagin A has E number E214.

Sodium ethyl para-hydroxybenzoate, the sodium salt of ethylparaben, has the same uses and is given the E number E215.

Uses of Nipagin A:
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 of Nipagin A:
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.

Pharmaceutical Applications of Nipagin A:
Ethylparaben is widely used as an antimicrobial preservative in cosmetics, food products, and pharmaceutical formulations.
Nipagin A may be used either alone or in combination with other paraben esters or with other antimicrobial agents. 

In cosmetics Nipagin A 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.

Storage of Nipagin A:
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 of Nipagin A:
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 Nipagin A 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.

Safety of Nipagin A:
Ethylparaben and other parabens are widely used as antimicrobial preservatives in cosmetics, food products, and oral and topical pharmaceutical formulations.
Systemically, no adverse reactions to parabens have been reported, although they have been associated with hypersensitivity reactions. Parabens, in vivo, have also been reported to exhibit estrogenic responses in fish.(10) The WHO has set an estimated total acceptable daily intake for methyl-, ethyl-, and propylparabens at up to 10 mg/kg body-weight.
LD50 (mouse, IP): 0.52 g/kg
LD50 (mouse, oral): 3.0 g/kg

Contact Allergens of Nipagin A:
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.

Dissolving in water of Nipagin A:
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 Nipagin A 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, Nipagin A 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 Nipagin A maximum solubility and any further quantities may be dissolved in the oil phase, or solvent, as appropriate.

pH stability of Nipagin A:
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:
Nipagin A is stable up to 80 °C

Solubility of Nipagin A:
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 of Nipagin A:
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 (%)
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 (%)
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

Properties of Nipagin A:
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 %

Names of Nipagin A:

IUPAC name of Nipagin A:
Ethyl 4-hydroxybenzoate

Other names of Nipagin A:
Ethyl paraben
Ethyl parahydroxybenzoate
Ethyl para-hydroxybenzoate
Ethyl p-hydroxybenzoate
4-Hydroxybenzoic acid ethyl ester

Synonyms of Nipagin A:
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
EPA Pesticide Chemical Code 061202
BRN 1101972
Ethyl chemosept
AI3-30960
Aseptine a
Nipagina A
Ethylester kyseliny p-hydroxybenzoove
Ester etylowykwasu p-hydroksybenzoesowego
PubChem20417
Ethyl 4-hydroxy-benzoate
Ethyl 4-hydroxyl-benzoate
Ethylparaben, INN, USAN
ACMC-209a7k
bmse010255
EC 204-399-4
p-Hydroxybenzoic ethyl ester
SCHEMBL28368
4-10-00-00367
Ethyl 4-Hydroxybenzoate,(S)
BIDD:ER0023
CHEMBL15841
Ethyl parahydroxybenzoate (TN)
ZINC1392
DTXSID9022528
ethyl 4-hydroxybenzenecarboxylate
CHEBI:31575
4-hydroxybenzoic acid-ethyl ester
NSC8510
Ethyl parahydroxybenzoate (JP17)
ETHYL PARA HYDROXY BENZOATE
HMS2091E17
Parahydroxybenzoic acid ethyl ester
Pharmakon1600-01400151
4-hydroxy benzoic acid ethyl ester
HY-B0934
NSC-8510
NSC23514
4-(Dimethylamino)benzenesulfonicacid
Tox21_111961
Tox21_300335
ANW-17502
BBL012166
BDBM50428380
NSC-23514
NSC755851
s4525
SBB038536
STK070911
AKOS000120512
Tox21_111961_1
CCG-213682
CS-4403
DB13628
MCULE-4906467392
NSC-755851
NCGC00160654-02NCGC00160654-03
NCGC00160654-04
NCGC00160654-06
NCGC00254462-01
AC-11586
AK-49315
AS-11988
NCI60_041866
SC-22680
SC-46755
SBI-0206674.P002
E-214
E0884
FT-0623514
FT-0626357
FT-0668364
ST50210582
4-FLUORO-3-METHYLPHENYLMAGNESIUMBROMIDE
A16012
A18133
D01647
Ethyl 4-hydroxybenzoate, ReagentPlus(R), 99%
M-3934
AB00375765_03
Q229976
SR-05000001552
SR-05000001552-1
W-108475
BRD-K02464583-001-01-4
Ethyl 4-hydroxybenzoate, SAJ first grade, >=99.0%
Ethyl 4-hydroxybenzoate, Vetec(TM) reagent grade, 99%
Ethylparaben, certified reference material, TraceCERT(R)
F0728-0009
UNII-AZF98361GV component NUVBSKCKDOMJSU-UHFFFAOYSA-N
4-Hydroxybenzoic acid-ethyl ester 1000 microg/mL in Acetonitrile
Ethylparaben, United States Pharmacopeia (USP) Reference Standard
Ethyl parahydroxybenzoate, European Pharmacopoeia (EP) Reference Standard
Ethylparaben, Pharmaceutical Secondary Standard; Certified Reference Material
E4B
 

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