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Propyl Gallate molbank Short Note Propyl Gallate Van Hai Nguyen 1,* , Minh Ngoc Le 1 , Hoa Binh Nguyen 1, Kieu Oanh Ha 1, Thai Ha Van Pham 2, Thi Hong Nguyen 3, Nguyet Suong Huyen Dao 1, Van Giang Nguyen 1, Dinh Luyen Nguyen 1 and Nguyen Trieu Trinh 4 1 Department of Pharmaceutical Industry, Hanoi University of Pharmacy, Hanoi 110403, Vietnam; [email protected] (M.N.L.); [email protected] (H.B.N.); [email protected] (K.O.H.); [email protected] (N.S.H.D.); [email protected] (V.G.N.); [email protected] (D.L.N.) 2 Department of Traditional Pharmacy, Hanoi University of Pharmacy, Hanoi 110403, Vietnam; [email protected] 3 Laboratory for Establishment of Reference Standards, National Institute of Drug Quality Control, Hanoi 11022, Vietnam; [email protected] 4 School of Environmental and Life Sciences, College of Engineering, Science and Environment, University of Newcastle, NSW 2308, Australia; [email protected] * Correspondence: [email protected]; Tel.: +84-918-971-109 Abstract: The title compound, propyl gallate (III), is an important substance popularly used in the food, cosmetic and pharmaceutical industries. Current chemical syntheses of this compound are based on the acylation supported by thionyl chloride, DIC/DMAP or Fischer esterification using a range of homogenous and heterogenous catalysts. In this paper, an efficient, green, straightforward, and economical method for synthesizing propyl gallate using potassium hydrogen sulfate, KHSO4, as the heterogenous acidic catalyst has been developed for the first time. In addition, this paper provides a comprehensive spectral dataset for the title compound, especially the new data on DEPT and 2D NMR (HSQC and HMBC) spectra which are not currently available in the literature. Citation: Nguyen, V.H.; Le, M.N.; Nguyen, H.B.; Ha, K.O.; Pham, T.H.V.; Keywords: antioxidant; esterification; potassium hydrogen sulfate; propyl gallate Nguyen, T.H.; Dao, N.S.H.; Nguyen, V.G.; Nguyen, D.L.; Trinh, N.T. Propyl Gallate. Molbank 2021, 2021, M1201. https://doi.org/10.3390/M1201 1. Introduction Academic Editor: Norbert Haider Propyl gallate (n-propyl gallate, n-propyl 3,4,5-trihydroxybenzoate, PG, compound III, CAS Registry number: 121-79-9) is an important synthetic substance widely used in Received: 29 March 2021 cosmetics, foods, pharmaceuticals, and some other fields [1–3]. It is used as an effective Accepted: 9 April 2021 antioxidant in cosmetics to stabilize vitamins, essential oils, perfumes, as well as fats and Published: 12 April 2021 oils [1]. In foods, PG has been employed as an additive (E310) since 1948 to protect fats, oils, and fat-containing food from peroxide-induced rancidity [1]. At a concentration Publisher’s Note: MDPI stays neutral of up to 0.1%, PG is used as a strong preservative and stabilizer in various medicinal with regard to jurisdictional claims in preparations approved by FDA [4,5]. In addition to its antioxidant activity, PG exhibits published maps and institutional affil- anti-inflammatory, anti-angiogenic, and anti-tumor properties [2–6]. iations. PG is not a natural compound and can only be obtained via chemical synthesis. In practice, PG is prepared by either biological (enzymatic) or chemical methods [2,7–13]. The latter have been dominant, focusing on the reaction between gallic acid (I) and n-propanol (propan-1-ol, II) in different conditions as illustrated in Scheme1[1–3,14–27]. Copyright: © 2021 by the authors. Experimentally, there are three main approaches to form PG from gallic acid Licensee MDPI, Basel, Switzerland. and n-propanol. The first approach is via a typical Steglich esterification with N,N0- This article is an open access article diisopropylcarbodiimide (DIC) as the coupling reagent and 4-dimethylaminopyridine distributed under the terms and (DMAP) as the catalyst [14]. However, urea generated by DIC as a by-product can some- conditions of the Creative Commons times be difficult to remove, especially when scaling up. In the second approach, thionyl Attribution (CC BY) license (https:// chloride is used as an additive to convert gallic acid to galloyl chloride which in turn read- creativecommons.org/licenses/by/ ily reacts in situ with n-propanol to form PG [15–17]. This approach requires rigorously 4.0/). Molbank 2021, 2021, M1201. https://doi.org/10.3390/M1201 https://www.mdpi.com/journal/molbank Molbank 2021, 2021, M1201 2 of 9 anhydrous conditions, i.e., dried gallic acid, freshly distilled thionyl chloride and total ex- clusion of water or the use of anhydrous solvents. The third approach utilizes direct Fischer esterification in the presence of various homogenous and heterogenous catalysts, including concentrated sulfuric acid (H2SO4), p-toluenesulfonic acid (p-TsOH), p-toluenesulfonic acid and sulfamic acid (p-TsOH + H2NSO3H), perchloric acid (HClO4), perchloric acid and sulfamic acid (HClO4 + H2NSO3H), ionic liquid N-methyl-2-pyrrolidonium hydrogen- sulfate ([Hnmp]HSO4), brominated sulfonic acid resin, mordenite (a zeolite mineral with orthorhombic structure containing calcium, sodium, potassium, aluminum, and silicate), and tetramethyl cucurbit[6]uril-phosphomolybdic acid (TMeQ [6]-PMA) (Table1)[ 18–27]. Scheme 1. Approaches for preparing propyl gallate (III) from gallic acid (I) and n-propanol (II). Table 1. The reported chemical methods for the preparation of PG. Catalyst or Time № T(◦C) Yield (%) Organic Solvent Purification Technique Ref Additive (h) 1 DIC/DMAP 0 7 66.0 THF Distillation, column [14] 70 5–6 73.0 EtOAc Distillation, extraction, column [15] 2 SOCl2 60–65 1 91.6 NU Precipitation [16] Reflux 5.5 NA EtOAc Extraction, crystallization [17] Reflux 4 NA NU Distillation, crystallization [18] 100 25 60.0 Isobutanol, n-butanol Distillation, crystallization [19] 130 8 NA CH2Cl2 Distillation, crystallization [20] 3 H SO 2 4 Reflux 8–12 74 Toluene Distillation, column [21] 95–100 5 56.5 NU Distillation, crystallization [2] Reflux Overnight 81.0 NU Distillation [22] Reflux 12 77.0 NA NA [23] 4 p-TsOH 107/MW 0.13 94.0 NA NA [23] 80–90 14 63.4 Benzene Distillation, crystallization [24] 5 p-TsOH + H2NSO3H 80–90 15 76.0 Benzene Distillation, crystallization [24] 6 HClO4 80–90 14 63.9 Benzene Distillation, crystallization [24] 7 HClO4 + H2NSO3H 80–90 15 81.6 Benzene Distillation, crystallization [24] 8 [Hnmp]HSO4 95–105 5 89.8 NU Distillation, crystallization [2] Brominated sulfonic 9 100 5 98.0 NU Distillation, crystallization [25] acid resin 10 Mordenite 70 5 96.2 NU Distillation, crystallization [26] 11 TMeQ[6]-PMA NCs 50–70 3-5 95.6 NU Distillation [27] T: reaction temperature, Ref: reference, DIC: N,N0-diisopropylcarbodiimide, DMAP: 4-dimethylaminopyridine, THF: tetrahydrofurane, NA: not available, NU: not used, Hnmp: 1-methyl-2-oxopyrrolidin-1-ium, p-TsOH: p-toluenesulfonic acid, MW: microwave, TMeQ[6]-PMA: tetramethyl cucurbit[6]uril-phosphomolybdic acid, NCs: nanocubes. Molbank 2021, 2021, M1201 3 of 9 In recent years, the study and development of heterogenous catalysts has received significant interest in different areas of organic transformations including the synthe- sis of PG. Heterogenous catalysts obtain many noticeable advantages, including their reusability, higher reaction rate and selectivity, easy product/catalyst separation, and affordability [28–31]. Among them, potassium hydrogen sulfate (potassium bisulfate, KHSO4) has emerged as an inexpensive, green, non-toxic, and easy to handle catalyst dis- playing high level of efficiency and reusability in many organic preparations [32]. However, the synthesis of PG using KHSO4 as a catalyst has not been yet reported. In relation to the spectroscopic characterization of PG, the current data are not complete and restricted to MS, IR, 1H, and 13C NMR data [33–35], while data on the pharmacological studies and physicochemical properties have been constantly updated [34–36]. Herein, we report an efficient, convenient, and economical synthetic procedure to obtain PG by Fischer esterification using KHSO4 as the sole heterogenous catalyst. At the same time, we provide a more complete spectral data set updating missing data on DEPT and 2D NMR (HSQC and HMBC) spectra for this compound. 2. Results and Discussion The target compound III was synthesized in 80.2% of yield from gallic acid monohy- drate (I) and n-propanol (II) using potassium hydrogen sulfate as the heterogenous acidic catalyst (Scheme2). ◦ Scheme 2. Synthesis of propyl gallate (III). Reagents and conditions: gallic acid: n-propanol: KHSO4 (1.0:12:0.40), 100 C, 12 h. A thorough search in Reaxys and SciFinder databases has returned a range of different methods for the preparation of PG. These methods are classified according to the usage of chemical catalysts or additives and summarized in Table1. Our synthetic procedure was based on [2,25,26] in entries 3, 9, and 10 of Table1. These methods were straightforward and offered a green pathway to obtain the final products without a using additional organic solvents and column chromatography. Using traditional catalysts such as concentrated sulfuric acid (H2SO4), p-toluenesulfonic acid (p-TsOH), and perchloric acid (HClO4), its mixture with sulfamic acid (H2NSO3H) afforded PG in moderate to excellent (56.5–94.0%, entries 3–7, Table1)[ 18–24]. However, these reactive catalysts can cause equipment corrosion problems, especially on a large scale. In addition, their use was usually accompanied by toxic and expensive solvents such as dichloromethane and benzene, as well as column chromatography to purify fi- nal products [19–21,24]. In [2], ionic liquid N-methyl-2-pyrrolidonium hydrogensulfate ([Hnmp]HSO4) was used as an efficient catalyst to afford PG in 89.8% of yield (entry 8, Table1). However, the preparation of this ionic liquid is quite complicated, and its regen- eration requires high energy to evaporate water from the filtrate. Recently, three [25–27] have demonstrated the synthesis of PG with excellent yield (up to 98.0%) and purity (up to 99.95%) using heterogenous catalysts, i.e.
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