Mini-Review on Various Analytical Methods for Determination of Certain Preservatives in Different Matrices

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International Journal of Research Studies in Science, Engineering and Technology Volume 8, Issue 2, 2021, PP 1-8 ISSN : 2349-476X DOI : https://doi.org/10.22259/2349-476X.0802001

Hisham Elrefay 1, Omnia A. Ismaiel 2, Wafaa S. Hassan2, Abdalla Shalaby 2, Ali Fouad 3, Mahmoud M. Sebaiy 4* 1 Simco Pharmaceutical industries, 6th of October, Egypt. 2 Department of Analytical Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt. 3 Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al-Azhar University, Assiut, Egypt. 4 Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt. *Corresponding Author: Mahmoud M. Sebaiy, Department of Medicinal Chemistry, Faculty of Pharmacy, Zagazig University, Zagazig, 44519, Egypt.

ABSTRACT In this literature mini-review, we will introduce mode of action and most of up-to-date reported methods that have been developed for determination of certain preservatives such as methylparaben, propylparaben, benzoic acid and potassium sorbate in their pure form, combined form with other drugs, combined form with degradation products, and in biological samples. Most of reported methods include spectrophotometric and chromatographic methods in addition to some electrochemistry methods. Keywords: mini-review; preservatives; methylparaben; propylparaben; benzoic acid; potassium sorbate.

INTRODUCTION been developed for determination of these drugs in different matrices. Preservatives have been used commonly as additives in pharmaceutical products, cosmetic, Methylparaben (Mpn) and food. Liquid preparations are particularly susceptible to microbial growth because of the nature of their ingredients. Such preparations are protected by the addition of preservatives, which prevent the alteration and degradation of the product formulation [1]. Preservatives are mainly effective in controlling mould, inhibiting yeast growth and preventing bacterial proliferation. Their antimicrobial and antifungal properties make them an integral part of the Chemical Name product formulation. Amongst the most Methyl 4-hydroxybenzoate [2]. commonly used preservatives in the conservation of liquid pharmaceutical preparations are sodium Molecular Formula benzoate, potassium sorbate, Propyl Hydro C H O xybenzoate (Propylparaben) and Methyl 8 8 3 Hydroxybenzoate (Methylparaben). The typical Molecular Weight concentrations of these substances allowed are 152.1 gm/mol. from 0.1% to 0.2%, from 0.1 to 0.2% and from 0.1% to 0.25% (w/w) respectively [1]. Physical Properties As such, in this mini-review article, four White or almost white, crystalline powder or preservatives have been studied in respect of colorless crystals. It is very slightly soluble in physical, chemical characters, mode of action water, freely soluble in ethanol (96 per cent) and and most reported analytical methods that have in methanol [2].

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Melting point Spectroscopic Methods 131°C [3]. Literature describes different spectroscopic methods for determination of MPN. A simple METHODS OF DETERMINATION method wasdeveloped for the determination of Official Methods MPN via oxidative coupling with the 2,4- Dinitrophynel hydrazine in the presence of N- The BP proposes a HPLC-UV method using bromosuccinimide in a basic medium, 0.15 m end-capped octadecyl silyl silica gel for Absorbance of the obtained colored products chromatography column and mobile phase of was measured at the corresponding optimum 35:65 V/V 6.8 g/L solution of potassium wavelengths (600 nm) [5]. dihydrogen phosphate, methanol, the detection was at 272 nm [2]. Chromatographic Methods The USP proposes a non-aqueous titration for Several chromatographic methods were the determination of MPN. The drug was described for the determination of the proposed dissolved in 1N sodium hydroxide followed by drug either in pure or in combination with other addition of methyl ethyl ketone then titration drugs summarized in Table 1. with 1 N sulfuric acid, determining the endpoint potentiometrically [4]. Table1. Chromatographic methods for the determination of MPN in pure form or in combination with other drugs. Drugs Method Column Mobile phase Detector λ Ref 0.005 mol/L ammonium acetate (10 mL triethylamine in 1 MPN, Ethylparaben, Hypersil GOLD L solution, pH Nipa-sol and HPLC UV 262 nm [6] C column adjusted to 5.0±0.5 Benzalkonium 18 with glacial acetic acid)-acetonitrile (45:55, V/V) Phenomenex MPN, Ethylparaben, Gemini C (5 Acetonitrile: water Propylparaben, and RP-HPLC 18 UV 254 nm [7] cm×4.6 mm, 5 (34:66, v/v), Butylparaben µm) Included water, methanol, acetonitrile, Methylisothiazolino- a 0.05% aqueous ne, solution of Methylchloroisothiazo (50 × 2 mm i.d.; trifluoroacetic acid, a HPLC UV 257 nm [8] linone, Benzyl alcohol, Merck) 0.1% aqueous solution Sodium benzoate and of formic acid and MPN mixtures thereof.gradient elution Mixture of acetonitrile, 2-phenoxyethanol, Lichrosorb C 8 tetrahydrofuran and MPN, Ethylparaben RP-HPLC (150×4.6 mm, 5 UV 258 nm [9] water (21:13:66, and Propylparaben µm) column v/v/v), MPN: MPN, An 151, 121 Mass Ethylparaben, Rtx-5MS capillary Propylpar GC–MS Helium spectrosco [10] Propylparaben and column aben: py Butylparaben 180, 138 m/z Toluene:Ethyl Ketoprofen, MPN, Silica gel 60 HPTLC acetate:Glacial acetic UV 265 nm [11] and Propyl Paraben F Merck plates 254 acid (6.5:2.5:1.0 v/v/v) MPN - propylparaben, Pre-coated n-pentane - glacial densitomet HPTLC 256 nm [12] Propylparaben - HPTLC plates, acetic acid (88:12, v/v) ry

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Butylparaben silica gel 60F254 for nano-TLC, 10x10 cm, Merck, West Germany. Acetonitrile:citrate Potassium sorbate, Eclipse XDB-C8 HPLC buffer, pH 4.0 (20:80 UV 260 nm [13] MPN, Propylparaben column v/v) Mobile phase A comprised of an 83:17 Betamethasone-17- A (v/v) mixture of valerate, Fusidic acid 100 mm × 3.0 mm acetonitrile and and Potassium sorbate RP-HPLC ID. Ascentis methanol and mobile UV 240 nm [14] as well as Methyl- and Express C18 phase B of a 10 g/l Propylparaben column solution of 85% phosphoric acid in purified water Potassium phosphate Spherisorb C Ethylparaben, MPN 18 buffer (pH7.05)- RP-HPLC column (250mm × UV 254 nm [15] and Propylparaben methanol (47.5:52.5, 4.6 mm) v/v) Equisil BDS, C , NaH PO : Methanol Levetiracetam, MPN 18 2 4 RP-HPLC 5 µm, (150 mm × in ratio of (55:45) pH UV 254 nm [16] and propylparaben 4.6 mm) 7.70 by NaOH

Miscellaneous Methods Chemical name: A voltammetric method using gold electrode Propyl 4-hydroxybenzoate. [2] was used for the electroanalytical determination Molecular formula of MPN in a pharmaceutical product and urine sample by cyclic, linear sweep and square-wave C10H12O3 voltammetric techniques. The oxidation of MPN Molecular weight is irreversible and exhibits a diffusion-controlled process. The oxidation mechanism was 180.2 gm/mol. proposed. The dependence of the current on pH. Physical properties It was found that the optimum buffer for the determination of MPN is pH of 7.0 [17]. A White or almost white, crystalline powder. It is method was developed for the determination of very slightly soluble in water, freely soluble in MPN using modified glassy carbon electrode ethanol (96 per cent) and in methanol [2]. based on a synthesized polypyrrole by Melting point differential pulse voltammetry. polypyrrole was covalently immobilized on glassy carbon 96-99°C [19]. electrode surface using tetraethyl ammonium METHODS OF DETERMINATION: perchlorate and acetonitrile. MPN was oxidized by differential pulse voltammetry and a peak Official methods was observed at 1.20 V [18]. The BP proposes a HPLC-UV method using PROPYLPARABEN (PPN) 0.15 m end-capped octadecyl silyl silica gel for chromatography column and mobile phase of 35:65 V/V 6.8 g/L solution of potassium dihydrogen phosphate, methanol, the detection was at 272 nm [2]. The USP proposes a non-aqueous titration for the determination of PPN. The drug was dissolved in 1N sodium hydroxide followed by addition of methyl ethyl ketone then titration with 1 N sulfuric acid, determining the endpoint potentiometrically [4].

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Chromatographic Methods drug either in pure or in combination with other drugs summarized in Table 2. Several chromatographic methods were described for the determination of the proposed Table2. Chromatographic methods for the determination of PPN in pure form or in combination with other drugs. Drugs Method Column Mobile phase Detector λ Ref. MPN, Ethyl, HPLC- Agilent Zorbax SB Propyl and Butyl Acetonitrile:water (50:50: v/v) UV 254 nm [20] DAD C narrow bore RR parabens 18 MPN and Propyl Buffer (pH 2.0) and acetonitrile HPLC UV 205 nm [21] paraben Waters 2489), column (68: 32)

Miscellaneous Methods water, soluble in boiling water, freely soluble in ethanol (96 per cent) and in fatty oils [2]. A selective and sensitive method was successfully developed for PPN determination Melting Point: in cosmetic sample using voltammetric sensor 121-125 °C [2]. for PPN based on a nanosized molecularly imprinted polymer–carbon paste electrode METHODS OF DETERMINATION [22]. Official Methods BENZOIC ACID (BZA) The BP [2] and the USP [4] proposes an acid base titration for the determination of BZA. The drug was dissolved in 20 mL of ethanol (96 per cent) then titrated with 0.1 M sodium hydroxide, using 0.1 mL of phenol red solution as indicator, until the color changes from yellow to violet-red. Chemical Name Spectroscopic Methods Benzene carboxylic acid [2]. Literature describes different spectroscopic Molecular Formula methods for determination of BZA in [23-25].

C7H6O2 Chromatographic Methods Molecular Weight Several chromatographic methods were described for the determination of the 122.1 gm/mol. proposed drug either in pure or in combination Physical properties with other drugs summarized in Table 3. White or almost white, crystalline powder or colorless crystals. It is slightly soluble in Table3. Chromatographic methods for the determination of BZA in pure form or in combination with other drugs. Drugs Method Column Mobile phase Detector λ Ref. Salicylic, 3- methyl Phenomenex Acetonitrile- Salicylic, 4- (Torrance, CA, phosphate buffer methyl USA) Kinetex 220–380 nm HPLC/ (pH 2.8; 2 mM) DAD [26] Salicylic, C , 4.6 mm x range 18 mixture (70:30, Acetylsalicylic 100 mm (2.6 v/v) and BZA μm).

PerfectSil 40%Acetonitrile Target C and 60% Sorbic and BZA HPLC-UV 18 UV 254 nm [27] thatwas ammonium purchased acetate buffer (5

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from Merck mmole/L;pH 4.4) (250 × 4.6 mm, 5 μm) Jasco PV- Methanol–acetate 1580 HPLC buffer (pH 4.4) BZA, Sorbic unit using a (35:65) acid, MPN and RP-HPLC Supelco 516 methanol–acetate UV 254 nm [28] PPN C column buffer (pH 4.4) 18 (15 cm×4.6 (50:50) mm, 5_m) thereafter. 90% ammonium Supelcosil LC- The importance Sodium C18,25 cm34.6 of food benzoate and mm, 5 mm, preservatives to 225 nm & HPLC UV [29] Potassium Supelco, consume- acetate 255 nm sorbate Bellefonte, PA, buffer with 10% USA. HPLC-grade acetonitrile Yanapak ODS-A column (250 Acetonitrile- BZA and mm x 4.6 mm HPLC water-acetic acid UV 235 nm. [30] Hippuric acid I.D., 7-pm (35:63:2, v/v/v) particles, Yanagimoto, Kyoto,Japan). 0.05 M potassium Equisil BDS, dihydrogen Risperidone and C , 5 µm, phosphate (pH RP-HPLC 18 UV 260 nm [31] BZA (150 mm × 4.6 2.5) and mm) acetonitrile (65:35; v/v)

Miscellaneous Methods Physical Properties An electro kinetic flow analysis–ion pair solid White or almost white, powder or granules. phase extraction–capillary zone electrophoresis It very soluble in water, slightly soluble in method for the determination of BZA and ethanol (96 per cent) [2]. sorbic acid in food products has been reported [32]. Melting Point Potassium Sorbate (SRT) 270 °C [33]. METHODS OF DETERMINATION: Official Methods The USP and BP proposes a non-aqueous titration for the determination of SRT. The drug was dissolved in glacial acetic acid, and titrated with 0.1 N perchloric acid VS to a blue-green endpoint using add 1 Chemical Name drop of crystal violet as indicator [2][4]. Potassium 2,4-hexadienoate [2]. Chromatographic Methods Molecular Formula Several chromatographic methods were described for the determination of the proposed C6H7KO2 drug either in pure or in combination with other Molecular Weight drugs summarized in Table 4. 150.2 gm/mol.

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Table4. Chromatographic methods for the determination of SRT in pure form or in combination with other drugs. Drugs Method Column Mobile phase Detector λ Ref. ACE-121- Ammonium acetate HPLC– 1504 C HPLC 225 and 18 buffer:acetonitrile UV UV column (15 cm _ 3.9 255 nm (72:28,v/v). Sodium benzoate mm I.D., 5 µm) [34] and SRT Phenomenex 150 _ 2 Ammonium acetate LC– mm, 4 l HPLC buffer:methanol (50:50, Mass spectroscopy MS/MS column. v/v).

SRT and Sodium C ‐ bonded Phosphate buffer (0.025 M, RP- 18 benzoate monolithic silica pH 2.0)–water–acetonitrile UV 230 nm [35] HPLC column (50:45:5, v/v/v)

Miscellaneous methods [4] United States Pharmacopoeia, N.F., USP302007: United States Pharmacopoeial A new potentiometric sensor, namely, Convention, Inc. Pt|Hg|Hg2(SOB)2 Graphite, where SOB stands [5] Ahmed, A.M.K., A.S. Khazaal, and A.H. for sorbate ion, are described constructed, Ahmed, Spectrophotometric Determination of evaluated and applied. The potentiometric Methyl Paraben in Pharmaceutical response is independent of the pH of the Formulations by Oxidative Coupling Reaction. solution in the pH range 6.0–9.0. The electrode Tikrit Journal of Pure Science, 2018. 21(6): p. was easily constructed at a relatively low-cost 85-89. with fast response time (within 15–30 s) and can [6] Tian, J., et al., Simultaneous Determination of 4 be used for a period of 4 months without Preservatives in Marketed Eye Drops by significant change in its performance HPLC. China Pharmacy, 2017. 28(15): p. 2134- characteristics. The proposed sensor displayed 2137. good selectivities over a variety of other anions [7] Kumar, S., et al., Development and validation (carboxylates and inorganic anions). of a single RP-HPLC assay method for analysis of bulk raw material batches of four parabens The potentiometric sensor was successfully that are widely used as preservatives in applied to the determination of sorbic acid in pharmaceutical and cosmetic products. Journal real food samples, that is, soft drinks, skim of chromatographic science, 2011. 49(5): p. yogurts, jams and sauces [36]. 405-411. [8] Baranowska, I., et al., Determination of CONCLUSION preservatives in cosmetics, cleaning agents and This literature mini-review represents an up to pharmaceuticals using fast liquid date survey about all reported methods that have chromatography. Journal of chromatographic been developed for determination of certain science, 2013. 52(1): p. 88-94. certain preservatives such as methylparaben, [9] Shabir, G.A., A new validated HPLC method propylparaben, benzoic acid and potassium for the simultaneous determination of 2- sorbate in their pure form, combined form with phenoxyethanol, methylparaben, ethylparaben other drugs, combined form with degradation and propylparaben in a pharmaceutical gel. Indian journal of pharmaceutical sciences, products, and in biological samples such as 2010. 72(4): p. 421-421. liquid chromatography, spectrophotometry, and [10] Han, Y., et al., DLLME Combined with GC–MS electrochemistry. for the Determination of Methylparaben, REFERENCES Ethylparaben, Propylparaben and Butylparaben in Beverage Samples. Chromatographia, 2010. [1] Remington, J.P., Remington: the science and 72(3-4): p. 351-355. practice of pharmacy. Vol. 1. 2006: Lippincott Williams & Wilkins. [11] Patil, P.M., S.B. Wankhede, and P.D. Chaudhari, Stability-indicating HPTLC method [2] The British, P., Volumes II and III, Her for simultaneous determination of Ketoprofen, Majesty’s Stationery Office2013, London, UK. Methyl Paraben and Propyl Paraben in gel [3] Almahy, H.A. and H.E. Khalid, Chemical formulation. Journal of Pharmacy Research, Examination of the Leaves Nerium oleander. 2013. 6(9): p. 945-953. International Journal of Tropical Medicine, [12] Tománková, H. and M. Pinkasová, 2006. 1(2): p. 58-62. Determination of Parabens and their

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Citation: Hisham Elrefay , Omnia A. Ismaiel , Mahmoud M. Sebaiy, et al ," Mini-Review on Various

Analytical Methods for Determination of Certain Preservatives in Different Matrices", International Journal of Research Studies in Science, Engineering and Technology, vol. 8, no. 2, pp. 1-8, 2021, DOI : https://doi.org/ 10.22259/2349-476X.0802001 Copyright: © 2021 Mahmoud M. Sebaiy. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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