Hindered phenols find a wide variety of applications across many different industry sectors. Butylated hydroxytoluene (BHT) is a most commonly used antioxidant recognized as safe for use in foods containing fats, pharmaceuticals, petroleum products, rubber and oil industries. In the past two decades, there has been growing interest in finding novel antioxidants to meet the requirements of these industries. To accelerate the antioxidant discovery process, researchers have designed and synthesized a series of BHT derivatives targeting to improve its antioxidant properties to be having a wide range of antioxidant activities markedly enhanced radical scavenging ability and other physical properties. Accordingly, some structure-activity relationships and rational design strategies for antioxidants based on BHT structure have been suggested and applied in practice. We have identified 14 very sensitive parameters, which may play a major role on the antioxidant performance of BHT. In this review, we attempt to summarize the current knowledge on this topic, which is of significance in selecting and designing novel antioxidants using a well-known antioxidant BHT as a building-block molecule. Our strategy involved investigation on understanding the chemistry behind the antioxidant activities of BHT, whether through hydrogen or electron transfer mechanism to enable promising anti-oxidant candidates to be synthesized.
New multipotent antioxidants (MPAOs), namely 1,3,4-thiadiazoles and 1,2,4-triazoles bearing the well-known free radical scavenger butylated hydroxytoluene (BHT), were designed and synthesized using an acid-(base-) catalyzed intramolecular dehydrative cyclization reaction of the corresponding 1-acylthiosemicarbazides. The structure-activity relationship (SAR) of the designed antioxidants was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antioxidant activity using DPPH and lipid peroxidation assays verified the predictions obtained by the PASS-assisted design strategy. Compounds 4a-b, 5a-b and 6a-b showed an inhibition of stable DPPH free radicals at a 10(-4) M more than the well-known standard antioxidant BHT. Compounds with p-methoxy substituents (4b, 5b and 6b) were more active than o-methoxy substituents (4a, 5a and 6a). With an IC50 of 2.85 ± 1.09 μM, compound 6b exhibited the most promising in vitro inhibition of lipid peroxidation, inhibiting Fe(2+)-induced lipid peroxidation of essential oils derived from the egg yolk-based lipid-rich medium by 86.4%. The parameters for the drug-likeness of these BHT derivatives were also evaluated according to Lipinski's 'rule-of-five'. All of the BHT derivatives were found to violate one of Lipinski's parameters (Log P ≥ 5) even though they have been found to be soluble in protic solvents. The predictive TPSA and %ABS data allow for the conclusion that these compounds could have a good capacity for penetrating cell membranes. Therefore, these novel MPAOs containing lipophilic and hydrophilic groups can be proposed as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.
A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10⁻⁴ M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe²⁺-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC₅₀ 16.07 ± 3.51 μM/mL) compared to α-tocopherol (α-TOH, 84.6%, IC₅₀ 5.6 ± 1.09 μM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.
Plant tissue or cell culture keeps a significant role in micro-propagation in the plant production industry. Combination of 6-Benzylaminopurine (BAP) and other plant growth regulators like 1-Naphthaleneacetic acid (NAA) or Indole-3-acetic acid (IAA) or indole-3-butyric acid (IBA) was used in the most of the research in tissue culture. The study was carried out to investigate the optimization of the concentration of IBA and BAP combination (0, 0.25, 0.50, 1.0, 1.50, 2.0, 2.5, 3.0 and 3.5 mg/l) for the root, callus and leaf proliferation from the leaf cutting slice. The highest number (6.75) of root proliferation was observed in the concentration of 2.0 mg/l IBA+0.25 mg/l BAP combination. The callus initiation was found in the concentration of IBA 1.0-3.5 mg/l+BAP 1.0-2.0 mg/l. However, the highest callus weight was observed at the concentration of IBA 1.5 mg/l+BAP 1.0 mg/l combination than other combination of concentrations. Positively leaf initiation and formation was better in the concentration of IBA 1-3.5 mg/l+BAP 1.0-2.0 mg/l combination. In addition, the 2,2-diphenyl-2-picrylhydarzyl (DPPH) free radical scavenging potential was higher (70.1%) in leaves extract than in callus extracts (46.3%) at the concentration of 10 mg/ml though both extracts had lower DPPH free radical scavenging activity compared to the positive control, vitamin C and BHT. Theresults conclude that the optimum concentration was IBA 1.5 mg/l+BAP 1.0 mg/l combination to produce callus cell proliferation and concentration of 2.0 mg/l IBA+0.25 mg/l BAP combination was the optimum for root proliferation of broccoli in vitro.
The present study was conducted to evaluate the antioxidant activity of Vernonia cinerea, Peperomia
pellucida and combination of Vernonia cinerea and Peperomia pellucida. These two herbs are pants that
often grow at random in different environments but are not commercialized due to the fact that no
comprehensive study of the importance of their use. The extract was prepared with methanol respectively.
1,1-diphenyl-2-picrylhydrazyl (DPPH) assay were used to study their antioxidant activity. The extracts
were compared with commercial antioxidant, butylated hydroxytoluene (BHT). The highest scavenging
effect from peel extract was presented by Vernonia cinerea with the value of 76.3% scavenging activity
(IC50 = 2.909), followed by the combination of Vernonia cinerea and Peperomia pellucida (71.21%
scavenging activity; IC50 = 5.274) and Peperomia pellucida with value of 68.3% scavenging activity (IC50
= 5.572). BHT showed the lowest IC50 value 1.71 with the scavenging activity 90.0%. Low IC50 value will
indicates the strong ability of the extracts to act as DPPH scavenger.
The present study was conducted to evaluate the antioxidant activity of peel extract from three types of
melon, Cucumis melo var cantalupensis, Cucumis melo var inodorus and Citrullus lanatus in family
Curcurbitaceae. The extract was prepared with methanol respectively. 1,1-diphenyl-2-picrylhydrazyl
(DPPH) assay were used to study their antioxidant activity. The extracts were compared with commercial
antioxidant, butylated hydroxytoluene (BHT). The highest scavenging effect from peel extract was
presented by Cucumis melo var inodorus with the value of 52.7 ± 9.1µg/ml (IC50 = 4.61). BHT showed
the lowest IC50 value 1.71 with the scavenging activity 90.0 ± 1.7µg/ml. Low IC50 value will indicates the
strong ability of the extracts to act as DPPH scavenger.
Mechanical properties of blended polyethylene (PE) containing the antioxidant Irganox 1010 and the UV-absorber Tinuvin 326 were studied for future use as radiation capsule material for the TRIGA Mark II research reactor. High density and low density polyethylene were blended with the additives and tested for elongation at break, impact strength and gel content, before and after irradiation inside the nuclear reactor. Characterization via FTIR as well as determination of crystallization and melt transition temperatures through DSC were also conducted. It was found that the addition of the antioxidant at different amounts (from 0 to 4 phr) had various effects on the properties of the blended PE, with 0 phr being the amount at which there was the biggest increase in elongation at break and impact strength, post-irradiation.
Butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and tert-butylhydroquinone (TBHQ) are synthetic antioxidants used in the food industry. Herein, we describe the development of a novel graphite nanocomposite-based electrochemical sensor for the multiplex detection and measurement of BHA, BHT, and TBHQ levels in complex food samples using a linear sweep voltammetry technique. Moreover, our newly established analytical method exhibited good sensitivity, limit of detection, limit of quantitation, and selectivity. The accuracy and reliability of analytical results were challenged by method validation and comparison with the results of the liquid chromatography method, where a linear correlation of more than 0.99 was achieved. The addition of sodium dodecyl sulfate as supporting additive further enhanced the LSV response (anodic peak current, Ipa) of BHA and BHT by 2- and 20-times, respectively.
The solubility limitations of phenolic acids in many lipidic environments are now greatly improved by their enzymatic esterification in ionic liquids (ILs). Herein, four different ILs were tested for the esterification of dihydrocaffeic acid with hexanol and the best IL was selected for the synthesis of four other n-alkyl esters with different chain-lengths. The effect of alkyl chain length on the anti-oxidative properties of the resulted purified esters was investigated using β-carotene bleaching (BCB) and free radical scavenging method DPPH and compared with butylated hydroxytoluene (BHT) as reference compound. All four esters (methyl, hexyl, dodecyl and octadecyl dihydrocaffeates) exhibited relatively strong radical scavenging abilities. The scavenging activity of the test compounds was in the following order: methyl ester>hexyl ester⩾dodecyl ester>octadecyl ester>BHT while the order for the BCB anti-oxidative activity was; BHT>octadecyl ester>dodecyl ester>hexyl ester>methyl ester.
The antioxidant activity and the total phenolic content, as well as the influence of petroleum ether, chloroform and methanol extracts from the leaves of Gynotroches axillaris, on microorganisms were studied. The total phenolic contents were evaluated by using Folin-Ciocalteu reagent and the obtained values ranged from 70.0 to 620 mg GAE/g. The efficiency of antioxidation, which was identified through the scavenging of free radical DPPH, exhibited that the highest IC50 was in the methanolic extract (44.7 µg/mL) as compared to the standard ascorbic acid (25.83 µg/mL) and to standard BHT (17.2 µg/mL). In vitro antimicrobial activity of extracts was tested against Gram-negative bacteria, Gram-positive bacteria and fungi. Methanol extract showed activity in the range (225-900 μg/mL) with both types, while petroleum ether and chloroform extracts were only active with Bacillus subtilis. The three extracts strongly inhibited all fungi with activity 225-450 μg/mL. The toxicity test against brine shrimps indicated that all extracts were non-toxic with LC50 value more than 1000 µg/mL. The finding of this study supports the safety of these extracts to be used in medical treatments.
Effect of supercritical CO2 extracted Nigella sativa L. seed extract (NE) on frying performance of sunflower oil and refined, bleached and deodorized (RBD) palm olein was investigated at concentrations of 1.2 % and 1.0 % respectively. Two frying systems containing 0 % N. sativa L. extract (Control) and 0.02 % butylated hydroxytoluene (BHT) were used for comparison. Physicochemical properties such as fatty acid composition (FAC), Peroxide Value (PV), Anisidine Value (AV), Totox Value (TV), Total Polar Content (TPC), C18:2/C16:0 ratio and viscosity of frying oils were determined during five consecutive days of frying. Results have shown that N. sativa L. extract was able to improve the oxidative stability of both frying oils during the frying process compared to control. The stabilizing effect of antioxidants were in the order of BHT > NE. RBD palm olein was found to be more stable than sunflower oil based on the ratio of linoleic acid (C18:2) to palmitic acid (C16:0) and fatty acid composition.
An HPLC method with ultraviolet-visible spectrophotometry detection has been optimized and validated for the simultaneous determination of phenolic compounds, such as butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) as antioxidants, and octyl methyl cinnamate (OMC) as UVB-filter in several personal care products. The dynamic range was between 1 to 250 mg/L with relative standard deviation less than 0.25% (n = 4). Limits of detection for BHA, BHT, and OMC were 0.196, 0.170, and 0.478 mg/L, respectively. While limits of quantification for BHA, BHT, and OMC were 0.593, 0.515, and 1.448 mg/L, respectively. The recovery for BHA, BHT, and OMC was ranged from 92.1-105.9%, 83.2-108.9%, and 87.3-103.7%, respectively. The concentration ranges of BHA, BHT, and OMC in 12 commercial personal care samples were 0.13-4.85, 0.16-2.30, and 0.12-65.5 mg/g, respectively. The concentrations of phenolic compounds in these personal care samples were below than maximum allowable concentration in personal care formulation, that is, 0.0004-10 mg/g, 0.002-5 mg/g, and up to 100 mg/g for BHA, BHT, and OMC, respectively.
This study was undertaken to evaluate the potential of fruit waste materials as source of natural antioxidant. The fruit peels including mango, guava and papaya peel were used in this study. The total phenolic content (TPC) was determined by Folin-Ciocalteu assay while antioxidant activities were determined by using ferric reducing antioxidant power (FRAP), 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, ferric thiocynate (FTC) and thiobarbituric acid (TBA) assays. These antioxidant activities were compared to synthetic antioxidants, BHA/BHT combination and ascorbic acid. The results demonstrated that TPC ranged from 3.23 to 15.84 g GAE/100 g extract. Mango peels extract exhibited highest TPC compared to guava peel and papaya peel extract. In the FRAP assay, mango peel extract at 200 ppm, guava peel extract at 400 ppm and papaya peel extract at 1200 ppm, exhibited reducing power comparable to the permissible amount of BHA/BHT at 200 ppm. At concentration of 250 μg/ml, the DPPH radical scavenging activity of extracts and standards decreased significantly in the order of mango peel extract > guava peel extract > BHA/BHT > ascorbic acid > papaya peel extract. For the FTC assay, the antioxidant activity of mango peel extract was significantly higher than ascorbic acid, guava peel and papaya peel extract but lower than BHA/BHT while in the TBA assay, percentage inhibition of BHA/BHT and ascorbic acid were found to be higher than fruit peel extracts. The quantitative analysis for flavonoids showed the presence of catechin, epicatechin and kaempferol in the peel extracts.
Efficacy of some Malaysian herbal aqueous extracts, BHA/BHT (synthetic antioxidants) and ascorbic acid in retarding oxidative rancidity was tested with cakes. The development of lipid oxidation products during 15 days at room temperature was evaluated by means of Peroxide Value (PV) and Thiobarbituric acidreactive substances (TBARS) value. The six formulations consists of control sample (cake without addition of antioxidant) (F1), cake added with curry leaves extract (F2), cake incorporated with kesum leaves extract (F3), cake added with tenggek burung leaves extract (F4), cake incorporated with ascorbic acid (F5) and cake added with BHA/BHT (F6). Formulation with the incorporation of tenggek burung leaves extract showed powerful oxidative stability effect compared to the formulations with othe plant extracts and control sample. However, cakes with BHA/BHT showed the strongest oxidative stability throughout the storage period. Therefore, it is suggested that tenggek burung leaves extract can be added into the food system for effectiveness as antioxidant to prolong the shelf life of the product.
This study was conducted on selected local herbs such as ulam raja (Cosmos caudatus), kesum (Polygonum minus), selom (Oenanthe javanica), pegaga (Centella asiatica) and curry leaves (Murraya koenigii) to investigate their antioxidative activities. The water extracts of the herbs were analysed for total phenolic content, reducing antioxidant power, ferric thiocyanate (FTC) and the thiobarbituric acid (TBA) test was also accried out. Polygonum minus showed the highest total phenolic content and reducing power among the herbs. Increasing the concentration of the extracts resulted in increased Fe3+ reducing antioxidant power for all the herbs. FTC and TBA tests on the extracts during seven days of storage showed that all the herbs extracts had the ability to reduce oxidation compared to the control (P < 0.05). From the FTC analysis, Murraya koenigii leaves was best in reducing the oxidation rate (67.67%) compared to the other herbs studied. Analysis of TBA showed that Centella asiatica extract had the highest antioxidant effect. However, both TBA and FTC analysis for these two herbs showed no significant difference (P >0.05) from Polygonum minus and butylated hydroxyanisole (BHT) a synthetic antioxidant. Correlation analysis showed positive correlations between amount of total phenolic content and reducing power (r = 0.75) and antioxidative activities (r = 0.58) in linoleic acid emulsion system. This shows that antioxidative activities of these Malaysian herbal plants especially Polygonum minus may be a potential source of natural antioxidants with similar characteristics to the synthetic antioxidant, BHT.
The effect of corn silk or Zea mays extract on the physicochemical changes of virgin coconut oil was studied during three consecutive days of deep frying. There were three types of oil blend systems used: virgin coconut oil without antioxidant as control system; virgin coconut oil with butylated hydroxytoluene (BHT) as synthetic antioxidant and virgin coconut oil with Zea mays extract as natural antioxidant. The oil quality was assessed by measuring the colour, viscosity, peroxide, p-anisidine, free fatty acids, totox and iodine value. The results show that Zea mays extract delayed the oil deterioration. The Zea mays extract significantly (p<0.05) lowered the rate of oxidation in virgin coconut oil compared to control oil and was comparable to BHT. Zea mays extract did not change the sensory profiles of French fries which was shown by insignificant difference (p<0.05) between Zea mays and control fries for all sensory attributes (colour, taste, aroma, crispiness, oiliness and overall quality). In general, the Zea may extract was capable of extending the stability and quality of virgin coconut oil and therefore has potential as new source of natural antioxidant for use in deep frying.
This study evaluated lipid oxidation in refrigerated (±4ºC) duck meatballs treated with novel antioxidants over 21 days of storage. The duck meatballs were treated with a control substance, Cosmos caudatus (ulam raja) or Polygonum minus (kesum) extract, or BHT (butylated hydroxytoluene), and data was collected every three days. These results showed that Cosmos caudatus and Polygonum minus had better antioxidant effects on duck meatballs than BHT or the control. Folding and microbial potency test results were not significantly different among the three antioxidants tested but were better in antioxidant-treated samples than in control samples. However, Cosmos caudatus and Polygonum minus were slightly more effective in preventing microbial growth. This result suggests that Cosmos caudatus and Polygonum minus may be potentially useful natural resources for enhancing the shelf life of duck meatballs.
The aim of this study is to determine the antioxidant capacity of underutilized fruits in Malaysia namely Milk apple (Syzygium malaccense), Malay apple (Syzygium malaccense (L.) Merr. and Perry), and Water apple (Syzygium aqueum). Synthetic antioxidants (BHA and BHT) commonly used in the food industries may not be as safe as it was presumed earlier. As BHA and BHT may be carcinogenic, it is important to look for new sources of natural antioxidants from fruits and vegetables. Freeze dried samples extracted with acetone and water were measured by ferric 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging and Ferric Reducing Antioxidant Power (FRAP) assays. Acetone extract (50%) showed higher values for both DPPH and FRAP assays compared with water extract. Milk apple has the highest DPPH value of 95.26% inhibition of DPPH. Milk apple also showed the highest FRAP value with 8722.22 µM of Fe (II) per gram of freeze dried sample. There was a significant difference (P < 0.05) in the types of extraction used. Antioxidant capacities of the samples are in the following order: Milk apple > Malay apple > Water apple. Proximate compositions and mineral contents of the samples were determined too. The samples can be used as a source of natural antioxidants.
Conjugated linoleic acids (CLAs) are a mixture of positional and geometric isomers of linoleic acid (LA) and believed to have many positive biological activities.
The aim of this study was to determine the effect of butylated hydroxytoluene (BHT), a lipid-soluble anti-oxidant added in different concentrations to the Tris egg yolk extenders on semen cytological parameters pre freezing and post thawing (motility, morphology, viability, acrosome integrity and membrane integrity) of Boer goat spermatozoa. A total of 40 ejaculates from four Boer goat bucks were collected using an artificial vagina. Ten replicates of the ejaculates were diluted with a Tris egg yolk based extender which contained various concentrations (0.5mM, 1.0mM, 2.0mM and 3.0mM) of butylated hydroxytoluene while one sample was processed without supplementation of antioxidant and served as control. The diluted semen was cooled at 4°C and loaded into the straw and then stored in liquid nitrogen. It was evident that supplementation of BHT produces positive effect in terms of motility, membrane integrity and acrosome integrity in comparison with the control group in cooled and frozen Boer goat semen. Results showed significant differences in motility, membrane integrity, acrosome integrity and viability of cooled and frozen Boer goat spermatozoa at different concentrations. Motility, membrane integrity, acrosome integrity and viability was significantly higher in all treated groups than the control group (P<0.05) while there was no significant differences (P>0.05) in morphology trait between all group in cooled semen. However, improvement (P<0.05) was observed only in terms of the membrane integrity and acrosome integrity compared to the control and other treated groups in frozen semen. In conclusion, BHT can be used in cryopreservation of Boer goat semen in order to reduce the oxidative stress on spermatozoa.