2014
DOI: 10.1107/s2053229614021445
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The antioxidant methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate

Abstract: The title compound, C18H28O3, was prepared by the reaction of 2,6-di-tert-butylphenol with methyl acrylate under basic conditions using dimethyl sulfoxide as the promoter. The structure of this antioxidant indicates significant strain between the ortho tert-butyl substituents and the phenolic OH group. In spite of the steric crowding of the OH group, it participates in intermolecular hydrogen bonding with the ester carbonyl O atom.

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Cited by 14 publications
(5 citation statements)
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“…In addition, the EC50 value of bee bread sample was measured as 80.08 ± 0.10 mg/mL. All values ranked it among the powerful antioxidant foods (Li et al, 2014). This high antioxidant property of EBB can be probably due to the functional compounds in its content such as phenolic compound (Methyl-3-(3,5-Ditertbutyl-4-Hydroxyphenyl)-Propionate), aromatic group (Benzo[G]Quinoline-2-Carboxylic-Acid), and terpenoid (Cholest-5-En-3-Ol(3Beta)) (Borawska et al, 2014;Greenland & Bowden, 1994;Khan et al, 2019).…”
Section: Resultsmentioning
confidence: 96%
“…In addition, the EC50 value of bee bread sample was measured as 80.08 ± 0.10 mg/mL. All values ranked it among the powerful antioxidant foods (Li et al, 2014). This high antioxidant property of EBB can be probably due to the functional compounds in its content such as phenolic compound (Methyl-3-(3,5-Ditertbutyl-4-Hydroxyphenyl)-Propionate), aromatic group (Benzo[G]Quinoline-2-Carboxylic-Acid), and terpenoid (Cholest-5-En-3-Ol(3Beta)) (Borawska et al, 2014;Greenland & Bowden, 1994;Khan et al, 2019).…”
Section: Resultsmentioning
confidence: 96%
“…Methyl ester of 3‐(3,5‐di‐tert‐butyl‐4‐hydroxyphenyl)‐propionic acid (Li et al . ), pyrrolo[1,2‐a]pyrazine‐1,4‐dione, hexahydro‐3‐(2‐methylpropyl) and pyrrolo[1,2‐a]pyrazine‐1,4‐dione, hexahydro‐3‐(phenylmethyl) (Ser et al . ) with retention time of 18·3, 18·5 and 22·9 min, respectively, are the three potent antioxidants in this FBE (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…), Methyl 3‐(3,5‐di‐tert‐butyl‐4‐hydroxyphenyl) propionate (Li et al . ), 1H‐Indole‐3‐propanoic acid (Bendheim et al . ), phenol, 2,4‐bis(1,1‐dimethylethyl) (Govindappa et al .…”
Section: Discussionmentioning
confidence: 99%
“…[Colour figure can be viewed at wileyonlinelibrary.com]a potential source of additional promising candidates for further investigation. Among the detected compounds 2 (3H)-Benzofuranone(Meng et al 2016), Methyl 3-(3,5di-tert-butyl-4-hydroxyphenyl) propionate(Li et al 2014), 1H-Indole-3-propanoic acid(Bendheim et al 2002), phenol, 2,4-bis(1,1-dimethylethyl)(Govindappa et al 2014;Padmavathi et al 2014;Rangel-S anchez et al 2014), hexadecanoic acid(Rahuman et al 2000;Kumar et al 2010;Aparna et al 2012), Cinnamic acid(Sova 2012) and 1H-Indole-3-carboxaldehyde(Naik et al 2012)…”
mentioning
confidence: 99%