Ethyl benzoate

Manufactured by Merck Group

Sourced in United States, Germany, China

Ethyl benzoate is a colorless, fragrant liquid organic compound commonly used in laboratory settings. It is a member of the ester family, formed by the reaction of benzoic acid and ethanol. Ethyl benzoate is a widely used solvent and chemical intermediate in various applications, including serving as a fragrance and flavoring agent.

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Close spelling variants of this product

Ethyl 4-dimethylamino-benzoate (EDMAB) (8 citations) Ethyl 4-dimethylamino benzoate (4-EDMAB, (3 citations) Ethyl-4-(dimethylamino)benzoate (EDB) (2 citations) Ethyl 4-dimethylamino-benzoate (EDAB) (2 citations)

14 protocols using ethyl benzoate

Synthesis and Characterization of Bioactive Compounds

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Auristatin derivatives were obtained from
Glykos Finland. (Helsinki, Finland). Hydrogen sodium phosphate, thiourea,
and the alkyl benzoates (m ethyl benzoate, ethyl benzoate, propyl benzoate,
butyl benzoate, pentyl benzoate, and hexyl benzoate) were purchased
from Sigma (Darmstadt, Germany). Naringerin, hesperetin, testosterone,
and aldosterone were purchased from Acros Organics (Belgium). Sulfadiazine,
naproxen, nadolol, sulfadimethoxine, sulfamethazine, and ketoprofen
were kindly donated by Prof. Michael Lämmerhofer (Tübingen
University, Germany). POPC, POPS, DLPC, and DMPC were purchased from
Avanti Polar Lipids (Alabaster, AL, USA). Methanol (HPLC-grade) and
dihydrogen sodium phosphate monohydrate were from Mallinckrodt Baker
(Deventer, Netherlands). Sodium hydroxide (0.1 M) was from FF-Chemicals
(Yli-Ii, Finland), and sodium dodecyl sulfate (purity 99%) was purchased
from Merck (Darmstadt, Germany).

Ruokonen S.K., Ekholm F.S, & Wiedmer S.K. (2019). Assessing the Interactions of Auristatin Derivatives with Mixed Phospholipid–Sodium Dodecyl Sulfate Aggregate Dispersions. Langmuir, 35(15), 5232-5240.

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Volatile Organic Compound Standards for Analytical Protocols

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The VOCs standards β-cis-ocimene, benzaldehyde (≥99%), cis-geraniol (≥97%), hexanal (≥95%), 1-hexanol (≥98%), ethyl benzoate, ethyl butanoate, ethyl hexanoate, ethyl octanoate, eucalyptol (≥99%), methyl benzoate, methyl butanoate (≥98%), 6-methyl-5-hepten-2-one, myrcene (≥90%), (R)-(+)-limonene (~90%), linalool (≥97%), α-pinene, 1-octen-3-ol (≥95%), γ-terpinene, terpinolene, (-)-terpinen-4-ol, trans-2-heptenal (≥95%), and C₇-C₄₀ n-alkanes mix were purchased from Sigma (Sigma-Aldrich, Saint Louis, MO, USA). All standards were of at least analytical grade.

Starowicz M., Błaszczak W., Ciska E, & Latocha P. (2022). Characterization of Volatile Organic Compounds in Kiwiberries (Actinidia arguta) Exposed to High Hydrostatic Pressure Processing by HS-SPME/GC-MS. Molecules, 27(18), 5914.

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Synthesis and Characterization of Benzoate Esters

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The compounds methyl benzoate (1), n-propyl benzoate(3), n-butyl benzoate (4), methyl 2-naphthoate (7), phenylacetate (9), ethyl 2-bromobenzoate (10), ethyl 3-bromobenzoate (11), ethyl 4-bromobenzoate (12), methyl 8-fluoro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate (methyl flumazenil ester, 16), methyl 4-aminobenzoate (methyl benzocaine ester, 14), and methyl [1,1′-biphenyl]-4-carboxylate (17) were synthesised at the Laboratório de Avaliação e Síntese de Substâncias Bioativas (LASSBio®, UFRJ, Brazil) with degree of purity ≥98%. Flumazenil (13) was purchased from Cristalia® – Brazil. Formic Acid (96%), acetonitrile and methanol of HPLC grade were purchased from Tedia®-Brazil. Water used for the HPLC analysis was produced using a water purification system (Master System MS2000, Gehaka, Brazil). Ethylbenzoate (2), phenylbenzoate (5), benzylbenzoate(6), methyl 2-phenylacetate (8), ethyl 4-aminobenzoate (benzocaine, 13), bicinchoninic acid kit for protein determination, ethylenediamine-tetra-acetic-acid (EDTA), monobasic and bibasic potassium phosphate, bis(p-nitrophenyl) phosphate sodium salt, magnesium chloride hexahydrate, β-nicotinamide adenine dinucleotide phosphate (NADP), D-glucose-6-phosphate, glucose-6-phosphate dehydrogenase, tetrahydrofuran (THF) and lithium hydroxide (LiOH) were purchased from Sigma Aldrich (St. Louis, MO, USA).

de Souza H.M., Guedes J.S., Freitas R.H., Gelves L.G., Fokoue H.H., Sant’Anna C.M., Barreiro E.J, & Lima L.M. (2022). Comparative chemical and biological hydrolytic stability of homologous esters and isosteres. Journal of Enzyme Inhibition and Medicinal Chemistry, 37(1), 718-727.

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Authentic Standards for Flavor Analysis

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Authentic standards, including acetic acid, phenylacetaldehyde, β-damascenone, dimethyl disulfide, decanal, 4-ethyl-2-methoxyphenol, ethyl benzoate, ethyl lactate, ethyl 3-methylbutanoate, ethyl phenylacetate, furfuryl alcohol, 2-methoxyphenol, limonene, linalool, methional, methyl salicylate, 3-methylbutanal, nonanal, phenylethyl alcohol, sotolone, 3-isobutyl-2-methoxypyrazine (IBMP), 3-methylbutanoic acid and isoamyl acetate were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA) or Sigma-Aldrich China Co. (Shanghai, China).

Li Z., Dong L., Jeon J., Kwon S.Y., Zhao C, & Baek H.H. (2019). Characterization and Evaluation of Aroma Quality in Doubanjiang, a Chinese Traditional Fermented Red Pepper Paste, Using Aroma Extract Dilution Analysis and a Sensory Profile. Molecules, 24(17), 3107.

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Volatile Identification and Enzyme Activity

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The chemicals used for volatile identification and enzyme activity, including hexyl acetate, E-2-hexenyl acetate, Z-3- hexenyl acetate, hexanol, E-2-hexenol, Z-3-hexenol, 2-octanol, butyl acetate, geranyl acetate, ethyl hexanoate, ethyl benzoate, MeJA, MeSA, JA, and SA were purchased from Sigma-Aldrich (USA).

Cao X., Duan W., Wei C., Chen K., Grierson D, & Zhang B. (2019). Genome-Wide Identification and Functional Analysis of Carboxylesterase and Methylesterase Gene Families in Peach (Prunus persica L. Batsch). Frontiers in Plant Science, 10, 1511.

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Synthesis and Characterization of Dyes

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Methyl chloroformate 98%, 3-amino phenol, ethyl acetoacetate, ethyl benzoate, diethylcarbonate 97% and 4-bromoacetophenone 98% were purchased from Sigma Aldrich (Germany) and used directly without any further purification. All solvents used (dioxan, dimethylsulfoxide, dimethylformamide, acetonitrile, acetic acid and acetone) were of spectroscopic grade. 100% polyester fabric (91 g/m², yarn count: dtex 44) was supplied by El-Mahalla El-Kobra Company, Egypt. The fabrics were scoured before application in an aqueous bath containing 2 g.L⁻¹ of nonionic detergent at 80 °C for 30 min to remove any processing oils and impurities. Thin-layer chromatography (TLC) was performed by a Kieselgel 60 F254 (Merck, Darmstadt, Germany), for observation of reaction progress and the purity of the prepared intermediates and synthesized dyes.

Aysha T., Zain M., Arief M, & Youssef Y. (2019). Synthesis and spectral properties of new fluorescent hydrazone disperse dyes and their dyeing application on polyester fabrics. Heliyon, 5(8), e02358.

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Quantitative Analysis of Volatile Compounds

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The following reference standards were purchased from Sigma-Aldrich (St. Louis, MO, USA): C7-C30 saturated alkane mixed standard, (internal standard) 2-methyl-3-heptanone, 2-methylpropyl 2-methylpropanoate, β-myrcene, β-trans-ocimene, ethyl hexanoate, 3-octanone, hexyl acetate, 2-methylbutyl 2-methylbutanoate, (Z)-3-hexenyl acetate, (Z)-hex-3-en-1-ol, 2-nonanone, 3-octanol, ethyl octanoate, (Z)-3-hexenyl butanoate, α-gurgujene, linalool, β-caryophyllene, (Z)-3-hexenyl (E)-2-butenoate, 2-undecanone, m ethyl benzoate, (Z)-3-hexenyl hexanoate, ethyl benzoate, humulene, α-farnesene, (Z)-3-hexenyl benzoate, and β-ocimene. All chemicals were of analytical grade or higher.

Peng Y., Bishop K.S, & Quek S.Y. (2019). Compositional Analysis and Aroma Evaluation of Feijoa Essential Oils from New Zealand Grown Cultivars. Molecules, 24(11), 2053.

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Volatile Ester Compound Isolation

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Ethyl acetate, ethyl 2-methylpropionate, propyl acetate, ethyl propionate, ethyl butyrate, isobutyl acetate, ethyl 2-methylbutyrate, ethyl 3-methyl butyrate, isoamyl acetate, ethyl valerate, butyl butyrate, ethyl hexanoate, isoamyl butyrate, propyl hexanoate, ethyl heptanoate, ethyl lactate, 3-methylbutyl hexanoate, propyl octanoate, ethyl nonanoate, hexyl hexanoate, ethyl 2-furoate, ethyl caprate, ethyl benzoate, ethyl phenylacetate, ethyl laurate, ethyl 3-phenylpropanoate, ethyl tetradecanoate, ethyl pentadecanoate, ethyl palmitate, ethyl oleate, and linoleic acid ethyl ester were obtained from Sigma-Aldrich (Shanghai, China). The internal standard (IS) was 2-octanol (Sigma-Aldrich, Shanghai, China). The linear retention index (RI) was determined with a C7–C30 n-alkane mixture (Sigma-Aldrich, Shanghai, China). All of the reagents used were of analytical grade with a purity of at least 97%, and most with a purity exceeding 99%. A Milli-Q purification system provided pure water (Millipore, Bedford, MA, USA). Sodium chloride (analytical grade) and absolute ethanol (analytical grade) were obtained from Sino-pharm Chemical Reagent Co., Ltd (Shanghai, China).

Niu Y., Liu Y, & Xiao Z. (2020). Evaluation of Perceptual Interactions between Ester Aroma Components in Langjiu by GC-MS, GC-O, Sensory Analysis, and Vector Model. Foods, 9(2), 183.

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Benzoate Derivatives: Pesticide Formulation

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M ethyl benzoate, Tween 20, Tween 80, ethyl benzoate, vinyl benzoate, n-propyl benzoate, n-butyl benzoate, benzyl benzoate, methyl 2-methylbenzoate, methyl 2-chlorobenzoate, methyl 2-methoxybenzoate, and methyl 2-nitrobenzoate were purchased from Sigma-Aldrich (St. Louis, MO). Compounds, iso-butyl benzoate, n-pentyl benzoate, and n-hexyl benzoate were purchased from Alfa Aesar (Tewksbury, MA). Methyl 3-methoxybenzoate (methyl m-anisate) and methyl 3-methylbenazoate (methyl m-toluate) were purchased from TCI America (Portland, OR). Acetone was used as solvent and purchased from Sigma-Aldrich (St. Louis, MO). All chemicals were used without further purification. Commercial pesticides: Distance insect growth regulator was purchased from Valent (Walnut Creek, CA), and TriStar 8.5 SL insecticide was purchased from Cleary Chemical (Alsip, IL). The active ingredients and corresponding concentrations for above commercial pesticides are listed in Table 3.

Feng Y., Chen J, & Zhang A. (2018). Commercially Available Natural Benzyl Esters and Their Synthetic Analogs Exhibit Different Toxicities against Insect Pests. Scientific Reports, 8, 7902.

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Characterization of Hungarian Jonathan Apple

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Apples (Malus domestica ‘Jonathan’, Csány 1) were collected beside the city of Székesfehérvár, located in central Hungary, in September 2019, and were transported to the laboratory for subsequent analysis. The Jonathan apple is a classic American variety, medium-sized apple, and widely regarded as one of the best flavored, with a good sweet/sharp balance. The Viniflora Concerto^TM (L. thermotolerans) and Melody^TM (mixed culture of T. delbrueckii, L. thermotolerans, and S. cerevisiae) starter cultures were obtained from Chr. Hansen A/S (Hoersholm, Denmark), while the Biodiva^TM Level 2 (Torulaspora delbrueckii TD291) and Uvaferm 228 (S. cerevisiae) of Lallemand Inc. (Montréal, QC, Canada) dry yeasts were purchased from Kokoferm Ltd. (Gyöngyös, Hungary). Standards (glucose, fructose, saccharose, acetic acid, lactic acid, succinic acid, acetaldehyde, methanol, isoamyl alcohol, 1-propanol, 1-butanol, 2-butanol, 2-phenylethanol, 1-hexanol, 2-methyl-1-butanol, trans-3-hexen-1-ol, cis-2-hexen-1-ol, benzyl alcohol, ethyl acetate, propyl acetate, ethyl hexanoate, ethyl butyrate, isoamyl acetate, phenylethyl acetate, diethyl succinate, ethyl octanoate, ethyl benzoate, ethyl formate, linalool), and all chemicals of analytical grade were obtained from Sigma-Aldrich (Steinheim, Germany).

Fejzullahu F., Kiss Z., Kun-Farkas G, & Kun S. (2021). Influence of Non-Saccharomyces Strains on Chemical Characteristics and Sensory Quality of Fruit Spirit. Foods, 10(6), 1336.

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